United States Court of Appeals For the First Circuit

No. 21-1983

UNITED STATES OF AMERICA,

Appellee,

v.

DEREK SHEEHAN,

Defendant, Appellant.

APPEAL FROM THE UNITED STATES DISTRICT COURT FOR THE DISTRICT OF MASSACHUSETTS

[Hon. Richard G. Stearns, U.S. District Judge]

Before

Barron, Chief Judge, Selya and Lynch, Circuit Judges.

Robert L. Sheketoff, with whom Sheketoff & O'Brien was on brief, for appellant. Donald C. Lockhart, Assistant United States Attorney, with whom Rachael S. Rollins, United States Attorney, was on brief, for appellee.

June 8, 2023 SELYA, Circuit Judge. Defendant-appellant Derek Sheehan

appeals both the district court's refusal to suppress the seizure

of his cell phone and its refusal to suppress evidence of child

pornography. We conclude that the seizure of the cell phone was

lawful, but that the warrant authorizing the search of his

electronic devices containing the child-pornography evidence was

neither supported by probable cause nor within the good-faith

exception to the warrant requirement. Accordingly, we affirm in

part and reverse in part the district court's denial of Sheehan's

motion to suppress, vacate both Sheehan's conviction and his

conditional guilty plea, and remand for further proceedings

consistent with this opinion.

I

When reviewing the disposition of a motion to suppress,

"[w]e rehearse the facts as supportably found by the district

court," supplementing those facts (as may be necessary) "with

uncontested facts drawn from the broader record." United States

v. Adams,

(1st Cir. 2020). With this standard in

mind, we first canvass the relevant facts and then trace the travel

of the case.

A

On June 28, 2018, a woman reported to police in Norwell,

Massachusetts, that Sheehan had sexually assaulted her younger

brother, who was a friend of Sheehan's son. A seven-week

- 2 - investigation followed, during which state and local police

conducted a series of interviews with several children and their

parents, all of whom were apparently acquainted with Sheehan and

his family.

From those interviews, the police learned of an

elaborate ruse through which Sheehan ostensibly had attempted to

dispel or preempt any suspicions the other parents might have had

that he was a pedophile. In a series of interviews, the parents

independently told a similar tale: that Sheehan had earlier said

that he had been the subject of a state police investigation after

text messages between two children describing him as a pedophile

had been unearthed by administrators at the children's school.

According to the parents, Sheehan said that the

investigation had exonerated him. In support, he showed them what

purported to be both a state police file and an email exchange

between him and the school resource officer. The parents described

the supposed police file as being hundreds of pages in length and

imprinted with the emblem of the Massachusetts State Police. But

all of this was made up out of whole cloth: unbeknownst to the

parents, Sheehan had never before been either the subject or the

target of any such investigation.

- 3 - Police officers also learned that Sheehan had created an

"Apple ID" account for the child he had allegedly assaulted.1 By

creating such an account, Sheehan was able to monitor that child's

text messages, pictures, and videos. Indeed, the police were told

that Sheehan had used a desktop computer in his home to spy on

that child's text messages. One of those messages, sent to another

child in January of 2018, described Sheehan as a "literal child

rpst [sic]."

On August 1, 2018, police officers tried to interview

Sheehan at his home. Because he was not there at the time, they

instead spoke to his wife. She denied ever having seen the state

police file described by the other parents. Before leaving,

though, the officers informed her that Sheehan was under

investigation.

On August 16, one of the parents called the Norwell

police to report that Sheehan and his wife had spoken to her by

telephone a few days earlier. Their stated intention was to deter

her from cooperating with the investigation. They told her, among

1 According to the affidavit submitted in support of the warrant to search Sheehan's home, the interview from which the police learned that Sheehan had created the Apple ID account occurred on August 17 (the day after the application for that warrant had been approved). It is unclear whether the date is a typographical error or whether the affidavit was somehow amended after the warrant issued. In all events, Sheehan does not challenge the warrant itself. Absent a better explanation, we assume — for argument's sake — that the date of the interview was recorded incorrectly.

- 4 - other things, that the police were dissembling about Sheehan and

could not be believed. In that conversation, Sheehan also told

the parent that she should inform the police that he had done

nothing wrong.

That evening, a Norwell police officer, Kayla Puricelli,

applied for a search warrant. The application expressly

incorporated by reference an attached affidavit, which described

the evidence gathered by the police during their interviews with

the parents and children. Additionally, the affidavit referred to

evidence, obtained by state police, that Sheehan had created two

email accounts. He created one such account in the name of the

school resource officer, and he created the other in the name of

the child whom he had allegedly assaulted.

Based on those facts, the affidavit stated that there

was probable cause to believe that Sheehan had committed the crimes

of identity fraud, unauthorized access to a computer, witness

intimidation, and impersonation of a police officer. See Mass.

Gen. Laws ch. 266, §§ 37E, 120F, ch. 268, §§ 13B, 33. To obtain

additional evidence of those crimes, the affidavit (and thus the

warrant application) sought authorization to seize, and

subsequently search, any electronic devices found within Sheehan's

home that could transmit or store digital data, including cell

phones. An assistant clerk of the Hingham District Court issued

the warrant (with docket number 1858SW0035), which authorized the

- 5 - search of Sheehan's house and person, but not the search of any

other person within the home.

The following morning — wielding an arrest warrant

separately obtained by the Massachusetts State Police — officers

arrested Sheehan for indecent assault and battery of a child under

the age of fourteen, see Mass. Gen. Laws ch. 265, § 13B, and

witness intimidation, see id. ch. 268, § 13B. The officers then

searched Sheehan's home pursuant to the warrant obtained by Officer

Puricelli, seizing myriad electronic devices in the process.2

Sheehan's wife had his cell phone in her possession at

the time of the search. While his arrest was taking place, Sheehan

asked his wife to call a lawyer. That is when the arresting

officers seized the phone: in Sheehan's words, one of the officers

"grabbed [his] wife by the arm, twisted her arm[,] and removed the

phone from her hand."3

2 In addition, the police seized a tobacco container, electronic cigarette cartridges, and three unopened bottles of root beer. It is not immediately apparent why the police believed that those items were responsive to the warrant, which authorized only the seizure of computers and electronic devices capable of storing or transmitting digital data. But because that issue does not bear directly upon the current appeal, we do not probe the point more deeply.

3 Sheehan's affidavit states that the search and arrest occurred on August 12. But the affidavit was entered into the record when Sheehan moved for reconsideration of the district court's denial of his motion to suppress the fruits of the August 17 search. Given both the context in which the affidavit was offered and the record as a whole, it can safely be assumed that the affidavit describes the August 17 search. The government

- 6 - Shortly thereafter, state prosecutors moved to impound

the search warrant because it contained information that could

possibly identify juvenile victims of sexual assault. On August

20, a justice of the Hingham District Court granted the motion.

On August 29, Officer Puricelli applied for a second

search warrant, this time seeking to search the electronic devices

seized from Sheehan's home for evidence of possession of child

pornography. See Mass. Gen. Laws ch. 272, § 29C. Like the first

warrant application, the second expressly incorporated an attached

affidavit. In that affidavit, Officer Puricelli stated that

because she had submitted the affidavit "for the limited purpose

of securing a search warrant," she had refrained from including

"each and every fact known to [her] concerning th[e]

investigation." Instead, the affidavit "set forth only those facts

that [she] believe[d] [were] sufficient to establish the requisite

probable cause for a search warrant."

The affidavit then recounted, in pertinent part, that a

seven-week police investigation had culminated in the issuance of

an arrest warrant for Sheehan and a search warrant for his home

(both of which were executed on August 17). The electronic devices

seized in that search were then taken into custody by the

Massachusetts State Police Computer Crimes Unit. A state trooper

asserts as much in its briefing, and Sheehan does not dispute the point.

- 7 - from that unit notified Officer Puricelli that — while downloading

digital evidence from Sheehan's phone — he had seen "pictures he

believed to be child pornography." According to the affidavit,

"[t]he pictures consisted of images of prepubescent penises that

lacked pubic hair." Based solely on that description and the fact

of Sheehan's arrest, the second application sought a warrant to

search all devices seized from Sheehan's home for evidence of

possession of child pornography.

Other than stating that Sheehan had been arrested for

indecent assault and battery on a child under the age of fourteen

in violation of Mass. Gen. Laws ch. 265, § 13B, the second

affidavit neither provided details of the alleged assault nor

recounted any facts drawn from the initial investigation. By the

same token, the second application did not contain copies of any

of the supposedly pornographic images. And although the affidavit

attached to the second application made clear that the devices to

be searched had been seized pursuant to the first search warrant

(which the second affidavit identified specifically by docket

number), the second affidavit at no point expressly incorporated

by reference the first search warrant, the application for that

warrant, or the affidavit furnished in support of that application.

Officer Puricelli did state in the second affidavit that

she had "previously submitted the same application relative to

[the electronic devices]," but she made pellucid that the prior

- 8 - application had been "based on probable cause for other crimes."

What is more, she stated that she had "not previously submitted

the same application" as it related to the crime of possession of

child pornography. (Emphasis in original). She also reiterated

that distinction on the form for the second warrant application.

An assistant clerk of the Hingham District Court — albeit

not the assistant clerk who approved the first warrant — authorized

the search. The second warrant issued with docket number

1858SW0036. The ensuing search uncovered videos of Sheehan

sexually abusing a child on three separate occasions. Based on

that evidence, he was charged in state court with several offenses,

including three counts of aggravated rape of a child in violation

of Mass. Gen. Laws ch. 265, § 22A.

B

Federal criminal charges followed. On September 19,

2018, a criminal complaint was filed in the United States District

Court for the District of Massachusetts, charging Sheehan with

three counts of sexual exploitation of children. See

(a), (e). On October 25, a federal grand jury returned an

indictment on those charges and added a child-pornography

forfeiture allegation, see

§ 2253.

In due season, Sheehan moved to suppress the evidence

obtained pursuant to both the first and second search warrants.

As relevant here, he contended that the police exceeded the scope

- 9 - of the first warrant by seizing his phone from his wife, given

that the warrant did not authorize the search of anyone in the

home (apart from Sheehan himself). He also contended that the

second warrant was unsupported by probable cause because the

application for the warrant neither attached a copy of the image(s)

to which the search was directed nor described the image(s) with

sufficient detail such that a neutral magistrate could determine

whether there was probable cause that the alleged object or objects

of the search were pornographic. See United States v. Brunette,

(1st Cir. 2001).

The district court was unconvinced. As to Sheehan's

phone, the court held that Sheehan lacked standing to contest the

seizure of his phone from his wife's possession. See United States

v. Sheehan, No. 18-10391,

, at *6 n.10 (D. Mass.

Jan. 28, 2020). So, too, it held that the description of the

allegedly pornographic images contained in the second warrant

affidavit was sufficiently detailed to establish probable cause

that child pornography would be found on the devices. See

. Accordingly, the motion to suppress was denied. See

. Sheehan moved for reconsideration, but the district court

summarily denied that motion.

On July 20, 2021, Sheehan entered a conditional guilty

plea, pursuant to a plea agreement, to all counts charged in the

indictment. See Fed. R. Crim. P. 11(a)(2). His plea was

- 10 - contingent upon the retention of his right to appeal the district

court's denial of his motion to suppress. On November 23, Sheehan

was sentenced to serve a 540-month term of immurement. This timely

appeal followed.

II

When reviewing a denial of a motion to suppress, we

examine the district court's "factual findings for clear error and

its legal conclusions, including its ultimate constitutional

determinations, de novo." United States v. Moss,

(1st Cir. 2019). We may uphold a suppression ruling on any ground

made manifest in the record. See id.; United States v. Ackies,

(1st Cir. 2019).

The Fourth Amendment provides that

[t]he right of the people to be secure in their persons, houses, papers, and effects, against unreasonable searches and seizures, shall not be violated, and no Warrants shall issue, but upon probable cause, supported by Oath or affirmation, and particularly describing the place to be searched, and the persons or things to be seized.

U.S. Const. amend. IV. Sheehan contends, as he did below, that

the evidence arrayed against him was obtained in violation of these

safeguards both because the police exceeded the scope of the first

search warrant and because the second search warrant was issued

without a sufficient showing of probable cause. We address these

contentions in turn.

- 11 - III

We start with Sheehan's remonstrances concerning the

seizure of his cell phone. "Whether a search exceeds the scope of

a search warrant is an issue we determine through an objective

assessment of the circumstances surrounding the issuance of the

warrant, the contents of the search warrant, and the circumstances

of the search." United States v. Pimentel,

(1st

Cir. 2022) (quoting United States v. Hitchcock,

(9th Cir.), amended on other grounds,

(9th Cir.

2002)). Here, the first search warrant unmistakably authorized

the police to search Sheehan's residence and his person in order

to seize any handheld digital devices or cell phones. It did not,

however, authorize the search of any other person.

Sheehan contends that the seizure of his phone was the

result of a warrantless search of his wife. He points to no

evidence to support this theory other than statements by the

government before the district court that the phone had been "with"

Sheehan's wife at the time of the search. Sheehan asserts that

such a statement is indicative of his wife having been searched by

the police and that, at the very least, additional evidence should

have been taken on the issue.

The district court declined to address this issue on the

merits. Instead, it held that Sheehan lacked standing to challenge

the seizure of the phone from his wife's possession. On appeal,

- 12 - the government does not press the standing issue but, rather,

invites us to affirm the district court's ruling on an alternative

ground: that no search of Sheehan's wife occurred and that the

seizure of the phone was within the scope of the warrant.

We accept the government's invitation and find its

arguments persuasive. "A search within the meaning of the Fourth

Amendment occurs whenever the government intrudes upon any place

and in relation to any item in which a person has a reasonable

expectation of privacy." Moss,

. There is no such

intrusion, though, when an object is simply held in one's hand and

the officer on the scene can see that the held object is subject

to seizure pursuant to the terms of a warrant. See United States

v. Corleto,

(1st Cir. 2022).

This is such a case. Sheehan points to no evidence that

the phone was concealed on his wife's person. Nor does he point

to any evidence that the police patted her down or rummaged through

her pockets to obtain it. Rather — according to Sheehan's own

account of events — the police pried the phone from her hand. What

Sheehan has described, then, is a seizure of personal property.

See United States v. Jacobsen,

(1984) (defining

a seizure of personal property as "some meaningful interference

with an individual's possessory interests in that property"). The

first search warrant authorized such a seizure, and Sheehan makes

no argument that — to the extent his wife was not searched — the

- 13 - seizure of the phone was not authorized by the warrant. We

therefore uphold the seizure of the phone under the first search

warrant.

IV

This brings us to Sheehan's argument that the second

search warrant was unsupported by probable cause. A finding of

probable cause "demands proof sufficient to support a fair

probability that a crime has been committed and that evidence of

that crime is likely to be found within the objects to be

searched." United States v. Coombs,

(1st Cir.

2017). When assessing whether such a finding is justified, we

look to the totality of the circumstances as they are set forth in

the warrant application and its accompanying affidavit, see

Illinois v. Gates,

(1983), mindful that "[t]he

probable cause standard 'is not a high bar,'" Adams,

(quoting Kaley v. United States,

(2014)).

That standard requires only "the kind of 'fair probability' on

which 'reasonable and prudent [people,] not legal technicians,

act.'" Florida v. Harris,

(2013) (alteration in

original) (quoting Gates,

).

Even so, "[s]ufficient information must be presented to

the magistrate to allow that official to determine probable cause;

his action cannot be a mere ratification of the bare conclusions

of others." Gates,

. Thus, in reviewing the

- 14 - issuance of a warrant, we look to "ensure that the magistrate had

a substantial basis for concluding that probable cause existed."

United States v. Joubert,

(1st Cir. 2015)

(quoting Gates,

).

In the court below, Sheehan challenged the second search

warrant on the ground that the second affidavit's description of

the nude images as seen by the state trooper was not sufficiently

specific to establish probable cause for possession of child

pornography. The court rejected that challenge, and Sheehan renews

it on appeal.

A

Sheehan's argument rests heavily on our decision in

United States v. Brunette, in which we held that a law enforcement

officer's assessment that images constituted child pornography

could not, on its own, support a finding of probable cause

sufficient to justify the issuance of a search warrant. See

. There, the affidavit submitted by the officer

stated that images linked to the defendant depicted "a prepubescent

boy lasciviously displaying his genitals" — a description that

simply parroted the statutory definition of child pornography

without providing any detail about the specific images in question.

at 17 (quoting United States v. Brunette,

(D. Me. 1999)); see

(2)(A)(v). We determined

that such "conclusory statutory language" could not alone

- 15 - establish probable cause because it left the magistrate without

sufficient facts from which to determine independently if the

images constituted child pornography. Brunette,

.

We also wrote, albeit in dictum, that "[a] judge cannot ordinarily

make [a probable cause] determination without either a look at the

allegedly pornographic images, or at least an assessment based on

a detailed, factual description of them."

.

Sheehan argues that the second affidavit's description

of "pictures consist[ing] of images of prepubescent penises that

lacked pubic hair" is equally conclusory and therefore

insufficient to ground a showing of probable cause. The government

demurs, insisting that the affidavit's description of the images

is far more specific than that offered in Brunette.

As a threshold matter, our probable cause inquiry is

shaped by the specific crime for which the police sought evidence.

The second warrant authorized the search of Sheehan's devices for

evidence of possession of child pornography as proscribed by state

law — not federal law (as was the case in Brunette). Compare Mass.

Gen. Laws ch. 272, § 29C with 18 U.S.C. § 2252A. For present

purposes, though, that is a distinction without a difference:

although Massachusetts law defines child pornography as conveying

a "lewd exhibition" of children (whereas federal law uses the term

"lascivious exhibition"), the Massachusetts Supreme Judicial Court

(SJC) has held that the state and federal definitions are

- 16 - synonymous. See Commonwealth v. Rex,

, 1069 n.14

(Mass. 2014). Thus, case law concerning the sufficiency of a

probable cause showing for possession of child pornography under

federal law may inform our analysis here.

Against this backdrop, we hasten to add that child nudity

alone does not make an image pornographic. See United States v.

Amirault,

(1st Cir. 1999); Rex,

.

Instead, the images at issue must be "lewd" (or in the federal

context "lascivious") in nature. See Mass. Gen. Laws ch. 272,

§ 29C;

(2)(A)(v). In making this determination,

courts consider the following factors:

1) whether the focal point of the visual depiction is on the child's genitalia or pubic area;

2) whether the setting of the visual depiction is sexually suggestive, i.e., in a place or pose generally associated with sexual activity;

3) whether the child is depicted in an unnatural pose, or in inappropriate attire, considering the age of the child;

4) whether the child is fully or partially clothed, or nude;

5) whether the visual depiction suggests sexual coyness or a willingness to engage in sexual activity; [and]

6) whether the visual depiction is intended or designed to elicit a sexual response in the viewer.

- 17 - Rex,

(alteration in original) (quoting United

States v. Dost,

(S.D. Cal. 1986)); see

Amirault,

(adopting Dost factors in review of

sentencing enhancement); Brunette,

(same in review

of probable cause determination for warrant).4 It follows that

the second affidavit's description of the images on Sheehan's phone

could only have established probable cause by providing enough

detail for the magistrate to determine — in light of those factors

— that the images seen by the state trooper were sufficiently

"lewd," such that they were indicative of child pornography.

We hold that the affidavit failed to cross this

threshold. Its cursory description that the trooper saw "images

of prepubescent penises that lacked pubic hair" did little more

than signify that the images contained child nudity. That

description offered no detail as to the focus of the images, how

the children were positioned in the images, or whether the images

were sexually provocative in any other respect. See Rex, 22 N.E.3d

at 1070-71. As was the case in Brunette, the affidavit here failed

We caution that although we find these factors "generally 4

relevant" and useful for the guidance they provide, they are "neither comprehensive nor necessarily applicable in every situation." Amirault,

. A determination of an image's lasciviousness "will always be case-specific." Id.; see United States v. Charriez-Rolón,

(1st Cir. 2019).

- 18 - to provide a "reasonably specific description" from which to assess

probable cause. Brunette,

.

The government asserts, unconvincingly, that the use of

the phrase "consisted of" in the warrant application's explanation

that "[t]he pictures consisted of images of prepubescent penises

that lacked pubic hair" denoted a focus on child genitalia. This

is whistling past the graveyard: the assertion that the images

"consisted of" genitalia means only that the genitalia was a

constituent part of the images. See 3 The Oxford English

Dictionary 772 (2d ed. 1989) (defining "consist of" as "to be made

up or composed of; to have as its constituent substance or

elements"). It says nothing as to the focus of the images. The

affidavit's description of the images thus failed to make the

necessary showing of lewdness needed to establish probable cause

of possession of child pornography.

B

That the description of the images in the second

affidavit — when viewed in isolation — failed to establish probable

cause does not end our inquiry. After all, Brunette addressed a

narrow circumstance in which the only proof offered to show

probable cause was the description of the allegedly pornographic

images. See

. Where, as here, an affidavit contains

additional facts probative of child pornography, we consider the

otherwise deficient image description within a broader context to

- 19 - determine whether the totality of the circumstances, as set forth

in the affidavit, justifies a finding of probable cause. See

United States v. Chiu,

(1st Cir. 2022).

In that respect, federal law differs from Massachusetts

law, which does not factor into the probable cause calculus "other

ancillary evidence that may be suggestive of the defendant's state

of mind," and instead focuses exclusively on evidence of "what is

visually portrayed in the pictures themselves." Rex,

n.13. Even so, evidence obtained by state officials while

investigating a violation of state law is admissible in federal

proceedings if it is obtained in conformity with the Constitution.

See United States v. Syphers,

(1st Cir. 2005).

Consequently, we must evaluate whether the second warrant

application and affidavit, taken as a whole, comported with the

requirements of the Fourth Amendment — regardless of the

requirements imposed by state law. See United States v.

Sutherland,

(1st Cir. 1991).

The issue, then, is whether those documents provided a

sufficient basis from which a neutral magistrate could

independently determine if the images that were the object of the

search were lewd in nature. To that end, the second affidavit

makes only a scant showing. In addition to the cursory description

of the images seen by the state trooper, the affidavit states that

after a seven-week investigation, Sheehan was arrested for

- 20 - indecent assault and battery of a child under the age of fourteen,

that the police searched his home pursuant to a search warrant,

and that the search yielded several electronic devices. Refined

to bare essence, the second affidavit offers only two unconnected

data points relevant to the probable cause determination: that

Sheehan was arrested for indecent assault and battery of a child

and that images of child nudity were seen on his phone.

Such a meager showing cannot establish probable cause.

It is true that "[p]robable cause does not require either certainty

or an unusually high degree of assurance." United States v. Morel,

(1st Cir. 2019) (quoting United States v. Clark,

(1st Cir. 2012)). Still, "[a]n affidavit must

provide the magistrate with a substantial basis for determining

the existence of probable cause." Gates,

. The

second affidavit provides almost no basis, never mind a substantial

basis, from which the magistrate could infer that Sheehan's phone

contained child pornography. It does not supply any additional

details about the alleged assault or Sheehan's pedophilic

tendencies. It does not state that Sheehan used a computer as

part of a ploy to prey upon children or that he recorded any of

his assaults. It does not even convey facts, or an opinion by the

affiant-officer based on training and experience, to suggest that

perpetrators of child sexual abuse frequently trade in child

pornography. The short of it is that nothing in the affidavit

- 21 - would permit a magistrate to infer that the assault for which

Sheehan was arrested increased (to the degree required by the

probable cause standard) the likelihood that evidence of child

pornography would be found on his phone. Conjecture or hunch

cannot fill this void.

In each previous case in which we have affirmed a

magistrate's finding of probable cause for possession of child

pornography, the challenged affidavit presented a far more robust

factual showing from which to conclude that the images sought were

child pornography. See Chiu,

(finding probable

cause when affidavit conveyed not only statements that defendant

viewed child pornography, but also evidence of defendant's online

behavior and his technical skill in surreptitiously obtaining

child pornography over internet); United States v. Burdulis,

(1st Cir. 2014) (finding that defendant's email

statements offering to send pornographic images to undercover

officer posing as a minor online, as well as defendant's

transmission of nude image of himself to officer, established

probable cause to search for child pornography). And we have ruled

before that an allegation of child sexual assault does not provide

probable cause to search a defendant's computer or electronic

devices in the absence of facts connecting the assault to the

devices in question. See United States v. Cordero-Rosario,

(1st Cir. 2015) (holding that probable cause was

- 22 - not established to search computer for evidence of child

molestation when affidavit included nothing more than fact that

defendant was under investigation for that crime and allegation of

pornography on computer); cf. Joubert,

(upholding search of electronic devices for evidence of child

molestation when affidavit stated that defendant photographed and

video-recorded his victims).

None of this is to say that evidence of child molestation

or sexual assault cannot in some instances be probative of

possession of child pornography. Such evidence may support a

finding of probable cause when the assault is presented within a

context that makes the possession of child pornography more likely.

See Syphers,

(considering in probable cause

analysis for possession of child pornography allegation that

defendant photographed and fondled minor girls, sexually explicit

pictures found in his home that featured minor girls, and evidence

that he accessed website trafficking in pornographic videos

featuring the same). But the affidavit must present that context

and cannot rely on the magistrate to presume a connection between

an assault charge and the possession of child pornography. See

United States v. Falso,

(2d Cir. 2008)

(holding that allegation that defendant attempted to access child

pornography website, combined with prior conviction for child

sexual abuse, was insufficient to show probable cause for search

- 23 - when no association between those two facts was "stated or

supported"); see also United States v. Perkins,

(9th Cir. 2017).

The bottom line is that a cursory description of images

of child nudity, coupled with the unconnected fact that the

defendant was charged with indecent assault and battery of a child,

does not, without further elaboration and factual support, suffice

to show probable cause of possession of child pornography. See

United States v. Pavulak,

(3d Cir. 2012); United

States v. Doyle,

(4th Cir. 2011). So it is

here — in the absence of additional proof establishing some

relation between those two facts, the magistrate was left without

any substantial basis from which to infer probable cause.

C

The government strives to persuade us that we should

expand the universe of facts available to the magistrate by

considering not only the information provided in the second

affidavit but also the "additional contextual and investigatory

details" provided in the first affidavit. We are not convinced.

Following the government's lead would offend the rule that we must

limit our assessment of probable cause to "information provided in

the four corners of the affidavit supporting the warrant

application." Morel,

n.10 (quoting United States

v. Vigeant,

(1st Cir. 1999)).

- 24 - The government tries to avoid this rule. In its view,

the second affidavit incorporated the first, such that the facts

in the first affidavit "must be considered as well" in the probable

cause determination. As we explain below, this "incorporation"

theory is woven entirely out of gossamer strands of speculation

and surmise and — as such — does not withstand scrutiny.

1

To begin, the government suggests that Sheehan has

waived the right to argue against its incorporation theory. In

advancing this suggestion, the government submits that the

district court held the first affidavit to be incorporated into

the second affidavit and that Sheehan waived any right to contest

that incorporation by failing to make the argument in his opening

brief. We reject the government's characterization of the district

court's order and, thus, reject its argument.

The district court's order stated — in its survey of the

facts of the case — that "Puricelli did not specifically

incorporate by reference her first affidavit." Sheehan,

, at *2 n.3. Even so, the court stated that it was reasonable

to infer "that the second [magistrate] would have been aware of

the earlier warrant issued by his court" because Officer Puricelli

had "four times listed the docket number of the first warrant" in

the second affidavit; because she had "disclosed that the first

application involved the seizure of the same items as named in the

- 25 - second [application]"; and because "the second warrant was given

the next successive docket number to the first."

It is

unclear, though, how such an inference — even if drawn — could be

said to come from within the four corners of the affidavit. And

in any event, the district court upheld the second warrant based

only on the second affidavit's description of the images, without

reference to any facts gleaned from the first affidavit. See

. Consequently, it was not incumbent upon Sheehan to

challenge an incorporation theory that the government has teased

from an off-hand, and ultimately superfluous, footnote in the

district court's order. Cf. United States v. Jurado-Nazario,

(1st Cir. 2020) (explaining that an argument is not

waived when party "brought the issue to the court's attention 'at

the earliest point when it was logical to do so'" (quoting Holmes

v. Spencer,

(1st Cir. 2012))).

2

This brings us to the merits of the government's

argument. The government concedes that the incorporation it

envisions was not done explicitly. It nonetheless argues that the

second affidavit implicitly incorporated the first for the reasons

articulated by the district court: that it referred to the first

warrant by its docket number, that the electronic devices to be

searched had been seized pursuant to that warrant, and that the

second warrant issued with a docket number successive to the first.

- 26 - From this concatenation of circumstances, we can assume, the

government insists, that the assistant clerk who authorized the

second warrant was aware of the facts contained in the first

affidavit (even though the first affidavit was not part of the

application for the second warrant).

The case law that it offers in support of this theory

cannot carry the weight that the government loads upon it. As an

initial matter, the line of cases cited by the government concerns

whether incorporated materials can cure defects in the

particularity or breadth of a search warrant. Those cases do not

directly address the incorporation of materials into a warrant

application.

Notwithstanding that distinction, we are aware of no

case — and the government has identified none — holding that the

mere mention of a document external to an affidavit (by docket

number or otherwise) implicitly incorporates the contents of that

document. Although the government cites cases signaling that no

specific verbiage is required for incorporation, those cases still

require language of some kind that expressly directs the reader's

attention to the purportedly incorporated materials. See, e.g.,

United States v. Lazar,

(6th Cir. 2010) (holding

that attachment's reference to "the below listed patients"

sufficed to incorporate patient list that accompanied warrant

application); United States v. SDI Future Health Inc., 568 F.3d

- 27 - 684, 700 (9th Cir. 2009) (upholding incorporation when warrant

used "suitable words of reference" that pointed explicitly to

incorporated material). There is certainly no support in the case

law for the proposition that merely alluding to a document, without

more, can alone suffice to incorporate that document by reference.

The government further contends that incorporated

materials need not physically accompany a warrant application that

is presented to a magistrate. But the cases that the government

cites in this regard address the separate issue of whether

incorporated materials must accompany a warrant during the

execution of a search. See, e.g., Baranski v. United States,

(8th Cir. 2008); United States v. Hurwitz,

(4th Cir. 2006). Nothing in those decisions

suggests that a magistrate — when determining whether sufficient

probable cause exists to authorize a warrant — may consider

unattached and external materials to which an affiant has only

obliquely alluded. What is more, the relevant case law in this

circuit holds that "[a]n affidavit may be referred to for purposes

of providing particularity if the affidavit accompanies the

warrant, and the warrant uses suitable words of reference which

incorporate the affidavit." Moss,

n.9 (alteration

and emphasis in original) (quoting United States v. Roche,

(1st Cir. 1980)); see United States v. Klein,

, 186 n.3 (1st Cir. 1977). Under this established circuit

- 28 - precedent, incorporation would require both suitable words to that

effect and the attachment of the affidavit. See generally United

States v. Barbosa,

(1st Cir. 2018) (explaining

law-of-the-circuit doctrine); United States v. Wogan,

(1st Cir. 1991) (same).

Those requirements were not satisfied here. Although

the second affidavit refers in passing to the first warrant by

docket number, it never specifically references the first

affidavit. That silence speaks volumes: it stands in stark

contrast to the express incorporation by reference of both

affidavits into their respective search warrant applications,

demonstrating that Officer Puricelli was aware of how to

incorporate documents properly into a warrant application. And

there is nothing in the record to suggest that the first affidavit

was attached to the second warrant application when it was

presented to the magistrate.

Finally, neither the second affidavit's reference to the

seizure of the items during the first search nor the fact that the

second search warrant issued with a docket number successive to

the first has much to do with the issue of incorporation. Together

those facts might, at most, suggest that Officer Puricelli

requested the second search warrant within the context of a larger

investigation. That suggestion, however, would be superfluous:

Officer Puricelli stated as much in the second affidavit. She

- 29 - explained that the affidavit did not include every fact that she

knew about the investigation but, rather, "only those facts [she]

believe[d] [were] sufficient to establish the requisite probable

cause for a search warrant." It defies logic to discount such an

express statement directing the magistrate to the probable cause

showing made within the affidavit itself in favor of a theory of

implicit incorporation based on a web of attenuated inferences.

On these facts, there is simply no basis for concluding that the

second affidavit incorporated the first.

D

The fatal deficiencies of the second affidavit were

therefore left unremedied, and the second search warrant issued

without the required showing of probable cause.

V

When a warrant issues without probable cause, the

evidence obtained from the resultant search is ordinarily

suppressed. See Pimentel,

. Suppression is

inappropriate, though, if the officer who conducted the search

acted in reliance upon the defective warrant and that reliance was

objectively reasonable. See Cordero-Rosario,

. This

exception, familiarly known as the "good-faith exception," is

grounded in the principle that "the purpose of suppression is to

deter police misconduct, and when law enforcement officers have

obtained a search warrant in good faith and acted within its scope,

- 30 - there is 'nothing to deter.'" Coombs,

(citation

omitted) (quoting United States v. Leon,

(1984)).

Notwithstanding the salutary considerations that have

spawned it, the good-faith exception is not a panacea for every

invalid warrant. Importantly, an officer cannot be said to have

relied on a warrant in good faith when the supporting affidavit is

"so lacking in indicia of probable cause as to render official

belief in its existence entirely unreasonable." Leon,

(quoting Brown v. Illinois,

(1975)

(Powell, J., concurring in part)). That a magistrate approved the

warrant despite its obvious deficiencies does not mitigate the

unreasonableness of the officer's conduct. See Vigeant,

; see also Malley v. Briggs,

, 346 n.9 (1986)

("The officer . . . cannot excuse [her] own default by pointing to

the greater incompetence of the magistrate."). And an officer's

reliance on a magistrate's approval of a facially deficient warrant

is especially unreasonable when those "deficiencies arise from the

failure of the [officer] conducting the search to provide the

required supporting information in the affidavit." Cordero-

Rosario,

; cf. Groh v. Ramírez,

(2004) ("[B]ecause petitioner himself prepared the invalid

warrant, he may not argue that he reasonably relied on the

Magistrate's assurance that the warrant contained an adequate

description of the things to be seized and was therefore valid.").

- 31 - In such circumstances, suppression "remains an appropriate

remedy." Leon,

.

"The government bears the burden of showing that its

officers acted with objective good faith." Brunette,

. In assessing the government's good-faith arguments, "we

evaluate all of the attendant circumstances at the time of the

warrant application and its execution."

Here, the government

has done little more than to state, in a conclusory fashion, that

there were sufficient facts indicative of probable cause such that

it was not objectively unreasonable for the officers to have relied

on the second search warrant. But the record, fairly read, belies

the government's optimistic characterization.

For a start, the second affidavit was "so lacking in

indicia of probable cause" that any reliance upon it was

objectively unreasonable. Leon,

. As we already

have discussed, see supra Part IV(B), the affidavit encompassed

little more than a cursory description of the images seen on

Sheehan's phone and the bare fact of his assault — a showing so

bereft of factual support that no reasonable officer would have

thought the warrant valid. See Doyle,

(holding

that evidence of molestation and possession of nude images not

enough to engender good-faith reliance that warrant for child

pornography was supported by sufficient probable cause); United

States v. Hodson,

(6th Cir. 2008) (finding good-

- 32 - faith exception did not apply when evidence of only child

molestation was used to obtain search warrant for child

pornography). And even though a magistrate ultimately approved

the warrant application, Officer Puricelli herself was responsible

for the warrant's defects: she had available a trove of other

information that she could have included in the warrant application

but which she chose to withhold. Her decision to submit a bare

bones affidavit and keep relevant data points to herself undercuts

any suggestion that she was justified in relying on the

magistrate's assurances of the warrant's legality. See Cordero-

Rosario,

.

When we have upheld searches for child pornography under

the good-faith exception, we have done so based on affidavits that

exhibited much more specificity and diligence than the second

affidavit here. See United States v. Robinson,

, 67-

70 (1st Cir. 2004) (upholding warrant on good-faith grounds when

affidavit included evidence that defendant had surreptitiously

photographed adolescents, viewed pornography on his computer

around minors, and asked a child to pose provocatively for him);

see also Syphers,

. So, too, other circuits —

in applying the good-faith exception — have done so only when the

affidavits at issue contained detailed information about the

history of the investigation and/or the defendant's pedophilic

predilections. See, e.g., United States v. Caesar,

,

- 33 - 174 (3d Cir. 2021) (holding good-faith exception applicable when

affidavit described receipt of tip from National Center for Missing

and Exploited Children, defendant's suspicious online behavior

seeking pictures of children in underwear, and evidence of sexual

abuse of two children); United States v. Edwards,

(10th Cir. 2015) (same when affidavit stated that defendant

had posted hundreds of images of child erotica, described some of

those images in detail, contained defendant's comments related to

those postings, and provided affiant-officer's opinion, based on

training and experience, that purveyors of child erotica also

possess child pornography). The affidavit prepared by Officer

Puricelli in connection with the application for the second search

warrant is conspicuously lacking in this level of detail.

Nor can it be said — even considering all the attendant

circumstances — that Officer Puricelli held an objectively

reasonable belief that her first affidavit was incorporated into

the application for the second search warrant. To be sure, the

second affidavit made clear that the devices to be searched had

been seized during a previous search of Sheehan's home and that a

prior warrant application concerning those items had been

submitted to the Hingham District Court. But those facts — whether

viewed singly or in the ensemble — do not form the basis for a

reasonable belief that the first affidavit was incorporated into

- 34 - the second when considered within the context of the record as a

whole.

The record shows that the second affidavit stated that

it did not contain all the facts that the police had uncovered

during their investigation but, rather, included only those facts

that Officer Puricelli believed were "sufficient to establish the

requisite probable cause for a search warrant." Giving due

consideration to that statement, it would be wholly unreasonable

for an officer to presume that the magistrate — in making the

probable cause determination — was to incorporate sub silentio

facts that had been expressly excluded from the affidavit. We

note, as well, that each warrant application explicitly

incorporated its supporting affidavit by reference. Seen in this

light, it strains credulity to suggest that a reasonable officer

would have intended to incorporate additional materials without

using any suitable language, especially when there is no evidence

that those materials were ever submitted to the assistant clerk as

part of the warrant application.5 And the final straw is that

Officer Puricelli noted on the second warrant application that her

5 For this reason, the case at hand is easily distinguished from those cases cited by our dissenting colleague, in which officers were deemed to have had a good-faith basis for believing in the incorporation of an affidavit that was attached to the warrant application and to which the warrant application in some way referred. See United States v. Tracey,

(3d Cir. 2010); United States v. Hamilton,

(8th Cir. 2010).

- 35 - previous application for the seizure of the devices had not made

out probable cause for the crime of child pornography. A

reasonable officer, acknowledging that fact, would have understood

the need for the second warrant application to establish probable

cause on its own.

Our dissenting colleague seems to suggest that because

the first warrant and its accompanying application had been

impounded, Officer Puricelli could reasonably have believed that

it was inappropriate either to attach or to directly refer to those

documents (even while expecting the assistant clerk to understand

that those documents were implicitly incorporated by reference).

But any such belief would surely have been unreasonable, given the

Supreme Court's decision in Groh v. Ramírez, in which reliance on

a facially deficient warrant that failed either to incorporate or

to attach a sealed affidavit (which would have cured the warrant's

deficiencies) was deemed objectively unreasonable.

. For purposes of a Fourth Amendment analysis, there

is no material difference between the impounded warrant here and

the sealed affidavit in Groh, see Pixley v. Commonwealth,

, 328 n.12 (Mass. 2009), and a reasonable officer would

have known that to rely on the impounded warrant without

incorporating it properly was contrary to law.

Relatedly, we add that the record does not support the

notion that Officer Puricelli may have entertained a reasonable

- 36 - belief that the assistant clerk was somehow apprised of the details

of Sheehan's case such that a proper showing of probable cause was

unnecessary. Although some personnel at the clerk's office of the

Hingham District Court may have been familiar with Sheehan's case

due to the first warrant application and the ensuing motion to

impound, each application or motion in this case was handled by a

different officer of that court. Short of rank speculation, there

is simply no basis from which to presume that the assistant clerk

who authorized the second search warrant was aware of the

investigatory information contained in the first affidavit.

We understand that the police have demanding jobs. The

good-faith exception is designed to cut police officers some slack

when they get close calls wrong. See Coombs,

.

The case at hand, however, does not fit that mold: it exhibits a

failure in what is a core competency of a police officer —

presenting sufficient probable cause of a crime to a neutral

magistrate to justify the issuance of a warrant. Under the

circumstances of this case, the good-faith exception does not

apply, and suppression of the evidence is required. See Leon,

.

VI

The expansion of the good-faith exception in Herring v.

United States,

(2009), to cases involving police

negligence does not alter our analysis. In Herring, the Supreme

- 37 - Court declined to apply the exclusionary rule to evidence obtained

by police after they effected an arrest pursuant to a facially

valid warrant, which — unbeknownst to them — had been recalled.

See

. The Court explained that "when police

mistakes are the result of negligence . . . , rather than systemic

error or reckless disregard of constitutional requirements," the

"marginal deterrence" gained by the exclusionary rule fails to

justify the "harm to the justice system" wrought by letting a

criminal go free.

. "To trigger the exclusionary

rule," Chief Justice Roberts wrote, "police conduct must be

sufficiently deliberate that exclusion can meaningfully deter it,

and sufficiently culpable that such deterrence is worth the price

paid by the justice system."

. Because the police

conduct in that case had not been "deliberate, reckless, or grossly

negligent," or the result of "recurring or systemic negligence,"

the Court declined to apply the exclusionary rule. Id.; see Davis

v. United States,

(2011) (stating that deterrent

effect of exclusionary rule is attenuated when police error stems

from isolated negligence).

The Herring Court took pains to anchor its holding to

precedent. See

. Far from breaking new ground,

Herring applied the rationale elaborated in Leon: that the

exclusionary rule should not be invoked when the rule's social

costs outweigh the benefits derived from deterring police

- 38 - misconduct. See Herring,

; see also Leon,

. Nothing in Herring suggests an expansion of the

good-faith exception to circumstances that Leon previously held to

be beyond the pale — such as the issuance of a warrant based on an

affidavit "so lacking in indicia of probable cause" as to render

any reliance on it "entirely unreasonable." Leon,

. That is the situation presented here.

We do not read Herring to require an additional or

individualized assessment of the deliberateness and culpability of

police conduct in such circumstances. Submitting a warrant

application so deficient in probable cause such that no officer

could reasonably rely upon it is exactly the kind of police conduct

the exclusionary rule is meant to deter. See

("[S]uppression is appropriate only if the officers were dishonest

or reckless in preparing their affidavit or could not have harbored

an objectively reasonable belief in the existence of probable

cause."); United States v. Fuccillo,

(1st Cir.

1987) (holding that failure to furnish affidavit with "information

which was known or easily accessible" to police reflected reckless

conduct to which good-faith exception did not apply). To hold

otherwise would expand the good-faith exception to swallow, in a

single gulp, the warrant requirement itself. That cannot be the

- 39 - law. If the good-faith exception is to have any limits, it cannot

encompass the police conduct that occurred here.6

VII

We need go no further. For the reasons elucidated above,

the district court's denial of the motion to suppress is affirmed

in part and reversed in part; the defendant's conviction and his

conditional guilty plea are vacated; and the case is remanded to

the district court for further proceedings consistent with this

opinion.

— Dissenting Opinion Follows —

Our dissenting colleague contends that the exclusionary rule 6

is inappropriate here because the first warrant supplied sufficient probable cause to search Sheehan's electronic devices in their entirety, rendering the second warrant altogether unnecessary. In support, she relies on the decision in United States v. Monell,

(1st Cir. 2015), but that reliance is misplaced. Monell itself distinguished Cordero-Rosario because, although the affidavit at issue in Cordero-Rosario "suffered from 'glaring deficiencies,'" the affidavit at issue in Monell "provide[d] probable cause to believe that a crime involving gun use had occurred, and that some evidence related to that crime was in [the] apartment" that was searched.

(quoting Cordero-Rosario,

). As we have explained, the second warrant issued in this case was supported by an affidavit that was insufficient for the same reasons that the affidavit in Cordero-Rosario was insufficient. Thus, Monell — on its own terms — is of no help to the government's argument that we should uphold the search conducted under the second affidavit on good-faith grounds. And to the extent that our dissenting colleague suggests that the first warrant, standing alone, provided an independently sufficient basis for the government to search Sheehan's electronic devices in a way that would have uncovered the images at issue, the government has made no such argument to us.

- 40 - LYNCH, Circuit Judge, dissenting. With respect, I

regret that the majority has improperly rejected the good-faith

exception to the exclusionary rule, which clearly applies here.

See United States v. Leon,

(1984); see also

Davis v. United States,

(2011); Herring v.

United States,

(2009). The majority errs in

concluding that the law of incorporation of earlier materials into

the second affidavit was so clear that the prophylaxis of

suppression is justified. And, regardless of whether the first

warrant was incorporated, exclusion is not justified on the cost-

benefit analysis described in Davis and Herring. Under binding

Supreme Court case law and First Circuit precedent, we are required

to affirm the district court's denial of the motion to suppress. I

dissent and would, as required by federal law, show greater respect

for the actions of the state judicial and law enforcement

officials.

The majority errs in holding that the second warrant,

dated August 29, 2018, was "based on an affidavit 'so lacking in

indicia of probable cause as to render official belief in its

existence entirely unreasonable,'" such that the good-faith

exception does not apply. Leon,

(quoting Brown v.

Illinois,

(1975) (Powell, J., concurring in

part)). In addition to recounting that Sheehan had been arrested

for indecent assault and battery of a child under the age of

- 41 - fourteen and that the Computer Crimes Unit officer found "images

of prepubescent penises that lacked pubic hair" on Sheehan's

iPhone, this affidavit referred four times to the first warrant by

its docket number. The affidavit also made clear that it concerned

items that had been seized pursuant to the first warrant. And the

second warrant application was given the very next docket number

after the first warrant. Even if one assumes arguendo that the

first warrant needed to be incorporated into the affidavit, a

dubious proposition, this first warrant supplied highly probative

information, such as the fact that a witness reported that Sheehan

had access to a young boy's "texts, pictures and videos" and

"sp[ied]" on him. And, as I describe later, suppression would not

be justified here regardless of whether the first warrant was

incorporated.

The majority discounts other facts about the second

warrant application that bear on the incorporation inquiry. The

Massachusetts state court that issued the warrant is the Hingham

District Court. It is a small court. There can be no doubt that

the judicial officer who authorized the second warrant was aware

of the first warrant. And between the issuance of the first

warrant and the application for the second warrant, the court had

impounded the first warrant, affidavit, and return.7 This order

7 "The terms 'impounded' and 'sealed' are closely related . . . . [A]n order of impoundment prevents the public, but

- 42 - further explains why the second affidavit referred to the first

warrant by docket number rather than including details from this

earlier warrant.8

The majority's reliance on Groh v. Ramírez,

(2004), to argue that a reasonable officer could not have believed

that the second warrant application incorporated the first warrant

and warrant application is misplaced for multiple reasons. First,

Groh addressed the very different question whether a warrant that

completely failed to identify the property to be seized was valid.

. This violated the particularity requirement expressly

set forth in the Fourth Amendment.

. Here, there is no

dispute that the second warrant application and affidavit

described the property to be seized with particularity. There was

no "glaring deficiency" in the warrant application akin to that at

issue in Groh.

.

Further, Groh did not turn on arguments about documents'

sealed status, and the Court did not make new law on this point.

The Court declined to "explore the matter of incorporation" at any

length because it accepted the premise that "the warrant did not

not the parties, from gaining access to impounded material, unless otherwise ordered by the court." Pixley v. Commonwealth,

, 328 n.12 (Mass. 2009).

8 In my view, the state court got it right when it issued the second warrant. That is so even before the good-faith exception is applied.

- 43 - incorporate other [sealed] documents by reference." Id. at 558;

see id. at 554-55, 557-58. Groh did not decide whether the fact

that a document is sealed or impounded bears on the reasonableness

of an officer's belief as to the sufficiency of efforts to

incorporate that document. See id. at 557-58.

Two final points on Groh bear note. To the extent the

decision mentioned the Leon good-faith exception, that reference

predates the Court's expansion of the good-faith doctrine in

Herring and Davis. And Groh itself was the product of a divided

Court, with Chief Justice Rehnquist and Justices Scalia, Kennedy,

and Thomas all in dissent.

It was reasonable for the officers to believe that the

many indicia of incorporation, in combination with the other facts

in the second warrant, sufficed to show probable cause. See United

States v. Tracey,

(3d Cir. 2010) ("Even though

we conclude these efforts [to expressly incorporate an affidavit]

were not legally sufficient . . . it would be reasonable for an

officer in [this officer's] position to believe the affidavit was

properly incorporated and, therefore, the warrant was valid.");

United States v. Hamilton,

(8th Cir. 2010)

(concluding that it was reasonable for an officer to rely on a

warrant "even if [the court] were now to conclude that the words

of incorporation [used in the warrant] were less than clear"). It

is clear that there is no overcoming of the principle announced in

- 44 - Leon. See

("'[A] warrant issued by a magistrate

normally suffices to establish' that a law enforcement officer has

'acted in good faith in conducting the search.'" (quoting United

States v. Ross,

, 823 n.32 (1982))).

The majority and I also disagree about the contours of

the Leon good-faith exception after Davis and Herring. As stated,

my view is that the majority’s holding fails even the Leon test.

It certainly fails under the doctrinal changes worked by Davis and

Herring, which further restricted the use of the exclusionary rule.

See, e.g., United States v. Caesar,

(3d Cir. 2021)

(describing, in a warrant-based search case, Davis and Herring as

"further refine[ments to] the [Leon] good faith exception, placing

the culpability of the officer's misconduct at the center of the

deterrence analysis" and stating that "[i]t could be said that

these [cases] . . . further narrowed the scope of the exclusionary

rule"); R. Re, The Due Process Exclusionary Rule,

, 1887 (2014) (describing Herring as providing "the

doctrinal basis for radically curtailing the circumstances in

which the Fourth Amendment exclusionary rule might apply").

Herring instructs that "[t]he fact that a Fourth

Amendment violation occurred . . . does not necessarily mean that

the exclusionary rule applies" and that the exclusionary rule

applies only where "the benefits of deterrence . . . outweigh the

- 45 - costs" of applying the rule.

.9 "To trigger

the exclusionary rule, police conduct must be sufficiently

deliberate that exclusion can meaningfully deter it, and

sufficiently culpable that such deterrence is worth the price paid

by the justice system."

. Thus, exclusion is typically

proper only where officers engage in "deliberate, reckless, or

grossly negligent conduct," or, "in some circumstances," where

there is "recurring or systemic negligence."

Applying these

principles, the Herring Court held that a negligent recordkeeping

error that led an officer to make an arrest based on a recalled

warrant should not result in exclusion of the evidence found during

the arrest. See

.

The Supreme Court reiterated this cost-benefit analysis

two years later in Davis. Davis emphasized that deterrence is

"the sole purpose of the exclusionary rule" and rejected the

argument that "facilitating the overruling of precedent" was a

relevant consideration.

.

Our circuit has repeatedly relied on Davis and Herring

to conclude that the good-faith exception applies where a police

mistake amounts to isolated negligence rather than intentional,

reckless, or grossly negligent misconduct. See United States v.

9 Herring involved a defendant who was "no stranger to law enforcement."

. Similarly, Sheehan had been under investigation for seven weeks before officers obtained an arrest warrant.

- 46 - Monell,

(1st Cir. 2015) (assuming warrant was

invalid but concluding that, under Herring, "the nature, effect,

and cause of this particular type of . . . invalidity are such as

to render the exclusionary rule inapplicable"); United States v.

Echevarría-Ríos,

(1st Cir. 2014) (finding good-

faith exception applicable where defendant failed to show that

officers engaged in intentional, reckless, or grossly negligent

misconduct in relying on procedurally defective warrant to arrest

him); see also United States v. Cruz-Ramos,

, 42 n.9

(1st Cir. 2021) (concluding that defendant waived applicability of

exclusionary rule where he did not engage in Herring cost-benefit

weighing analysis); United States v. Thomas,

(1st Cir. 2013) (concluding that social costs of excluding DNA

sample obtained in earlier investigation would outweigh deterrent

value).

Here, there can be no possible deterrent effect to be

accomplished by excluding the evidence on the cost-benefit

analysis described in Davis and Herring. See United States v.

Szczerba,

(8th Cir. 2018) (applying good-faith

exception where officer "acted negligently in drafting the

warrant . . . [and] should have . . . ensured that the supporting

affidavit was incorporated into the warrant," but her "conduct

certainly did not reflect the type of deliberate, reckless, or

- 47 - grossly negligent disregard for the Fourth Amendment that the

exclusionary rule can effectively deter").

That there could be no possible deterrent effect is

underscored by the fact that the officers here need not have taken

the cautious measure of applying for a second search warrant to

search the devices seized under the first warrant. The first

warrant authorized officers to search Sheehan's devices for

"computer data files or cellular / smart phone data files" in

relation to the four crimes set forth in that warrant:

impersonation of a police officer, witness intimidation,

unauthorized access to a computer system, and identity fraud. See

Mass. Gen. Laws ch. 266, §§ 37E, 120F; id. ch. 268, §§ 13B, 33.

This situation is thus similar to Monell, where we applied the

good-faith exception to a labeling error in an affidavit because,

if this error had not occurred, "there still would have been a

search" on a different basis, "that search would have been valid,"

and "precisely that evidence which was found in the search

challenged here would have been found in [the] valid search."

. The majority attempts to distinguish Monell by

contending that its rule applies only when the affidavit at issue

is not "glaring[ly] deficien[t]." (Quoting

.) Even

assuming the validity of that premise, here -- for all the reasons

- 48 - previously stated -- the second affidavit is not "glaringly

deficient."

With the greatest respect for my colleagues, I dissent.

- 49 -