United States Court of Appeals For the First Circuit

No. 17-1930

UNITED STATES OF AMERICA,

Appellee,

v.

HUGO SANTANA-DONES, t/n Rafael Jose Ventura, a/k/a Raffi, a/k/a Rafael Ventura, a/k/a Hugo Santana, a/k/a Wilthron Flores,

Defendant, Appellant.

No. 17-1970

UNITED STATES OF AMERICA,

Appellee,

v.

ELVIS GENAO, a/k/a Cocolo,

Defendant, Appellant.

No. 17-2103

UNITED STATES OF AMERICA,

Appellee,

v.

FELIX MELENDEZ, a/k/a Felo, a/k/a Felito,

Defendant, Appellant. No. 17-2113

UNITED STATES OF AMERICA,

Appellee,

v.

OSVALDO VASQUEZ, a/k/a Chu Chu, a/k/a Anthony Christopher,

Defendant, Appellant.

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

[Hon. Timothy S. Hillman, U.S. District Judge]

Before

Lynch, Selya, and Boudin, Circuit Judges.

Karen A. Pickett and Pickett Law Offices, P.C. on brief for appellant Santana-Dones. Leslie W. O'Brien on brief for appellant Genao. Alan Jay Black on brief for appellant Melendez. Marie Theriault on brief for appellant Vasquez. Andrew E. Lelling, United States Attorney, and Alexia R. De Vincentis, Assistant United States Attorney, on brief for appellee.

March 29, 2019 SELYA, Circuit Judge. For the most part, these

consolidated appeals turn on a single issue: whether the district

court erred in concluding that the court which issued the wiretap

warrant could have found the facts in the application to be at

least minimally adequate to support the issuance of the warrant.

We resolve that issue favorably to the government, conclude that

the defendants' unified challenge to the wiretap is unavailing,

determine that the separate claims of error mounted by one of the

defendants are meritless, and affirm the judgments below.

I. BACKGROUND.

We rehearse here only those facts necessary to place

these appeals in perspective. In the summer of 2014, the Drug

Enforcement Administration (DEA), assisted by local law

enforcement officers, began investigating the drug-trafficking

activities of defendant-appellant Osvaldo Vasquez and his cohorts,

including defendants-appellants Hugo Santana-Dones, Elvis Genao,

and Felix Melendez. During the next year, the investigators relied

heavily on two confidential sources, who were buyers, to gather

evidence of the defendants' drug-trafficking activities. All

told, these confidential sources carried out controlled purchases

of nearly 500 grams of heroin and heroin laced with fentanyl and

methamphetamine. They also arranged to purchase at least one

kilogram of cocaine.

- 3 - DEA agents supplemented the efforts of these

confidential sources through traditional investigative techniques

such as physical surveillance and the use of a pen register. In

September of 2014, the agents obtained a warrant from a federal

magistrate judge, pursuant to

and Federal Rule of

Criminal Procedure 41(e)(2)(C), authorizing the installation of a

GPS tracking device on a vehicle driven by Vasquez during certain

observed drug sales. The agents then went a step further and,

from April to July of 2015, made use of a wiretap of Vasquez's

cellular telephone, which had been authorized and periodically

renewed by a federal district judge pursuant to

.

Matters came to a head in August of 2015 when DEA agents,

accompanied by local officers, executed search warrants at six

locations linked to the defendants (five in Massachusetts and one

in Rhode Island). Arrest warrants had also been obtained and all

four defendants were arrested at that time. Large quantities of

heroin and cocaine, as well as drug paraphernalia and a firearm,

were recovered in the process.

The next month, a federal grand jury sitting in the

District of Massachusetts handed up an indictment charging all

four defendants with conspiracy to distribute and to possess with

intent to distribute heroin and cocaine and distribution and

possession with intent to distribute heroin and/or cocaine. See

(a)(1), 846. Vasquez alone was charged with

- 4 - possession of a firearm in furtherance of a drug-trafficking crime.

See

(c). All the defendants initially maintained

their innocence and moved to suppress any and all evidence

garnered, directly or indirectly, through the use of the wiretap.

The defendants argued that the affidavit in support of the

application for the wiretap failed to satisfy the statutory

requirement that the government demonstrate necessity. See

(1)(c). The government opposed the motion.

Following a non-evidentiary hearing, the district court took the

matter under advisement and, on October 11, 2016, found the showing

of necessity sufficient and denied the motion.

Starting around this time, Vasquez experienced a number

of changes in his legal representation. Counsel 2A and 2B,

appointed just before Vasquez's arraignment, withdrew shortly

after the denial of the motion to suppress, citing a breakdown in

the attorney-client relationship. Vasquez's next attorney

(Counsel 3) represented him for less than a month before

withdrawing on December 5 due to a conflict. His successor

(Counsel 4) was appointed on December 8, 2016.

Less than one month later, Vasquez moved for a 90-day

extension of time to file additional motions to suppress. The

government opposed the motion, and the district court denied it on

January 24, 2017. The court subsequently rejected Vasquez's motion

for reconsideration.

- 5 - In due course, the four defendants pleaded guilty to all

the charges, reserving the right to challenge the district court's

suppression-related rulings and to claim ineffective assistance of

counsel. See Fed. R. Crim. P. 11(a)(2). After accepting the

quartet of pleas, the district court sentenced Santana-Dones to

serve an 80-month term of immurement; sentenced Genao to serve 37

months; sentenced Melendez to serve 70 months; and sentenced

Vasquez (whom both the government and the court regarded as the

ring leader) to serve 125 months. These timely appeals followed,

and we consolidated them for briefing and oral arguments. On

appeal, all of the defendants pursue their challenges to the

suppression-related rulings but only Vasquez attempts to pursue an

ineffective assistance of counsel claim.

II. THE WIRETAP EVIDENCE.

"When assaying a district court's ruling on a motion to

suppress wiretap evidence, we review its factual findings for clear

error and its legal conclusions de novo." United States v. Gordon,

(1st Cir. 2017). Applying this standard, the

pivotal question is whether "the facts set forth in the application

were minimally adequate to support the determination that was

made." United States v. Villarman-Oviedo,

(1st Cir.

2003) (quoting United States v. Ashley,

(1st

- 6 - Cir. 1989)).1 The district court answered this question in the

affirmative and, to find clear error, we "must form a strong,

unyielding belief, based on the whole of the record, that a mistake

has been made." United States v. Rodrigues,

(1st

Cir. 2017) (quoting United States v. Siciliano,

(1st Cir. 2009)). Put another way, we will "affirm under the clear

error standard 'if any reasonable view of the evidence supports'

the district court's finding."

(quoting Siciliano,

).

In this instance, "[o]ur inquiry is guided by Title III

of the Omnibus Crime Control and Safe Streets Act of 1968,

, which governs the rules for federal telephone

wiretaps." United States v. Rose,

(1st Cir.

2015). "Title III provides a comprehensive scheme for the

regulation of electronic surveillance, prohibiting all secret

interception of communications except as authorized by certain

state and federal judges in response to applications from specified

federal and state law enforcement officials." Rodrigues,

(quoting Dalia v. United States,

(1979)).

1 Santana-Dones acknowledges that this is the correct standard of review under our circuit precedent, but "wishes to preserve for the record [the argument] that such a standard does not comport with statutory requirements or with due process under the Fifth Amendment because it relieves the Government of its burden of proof." Given his concession, we need not dwell upon the argument that he wishes to preserve.

- 7 - Congress has made pellucid the law's main purposes: "(1)

protecting the privacy of wire and oral communications, and (2)

delineating on a uniform basis the circumstances and conditions

under which the interception of wire and oral communications may

be authorized." Gelbard v. United States,

(1972)

(quoting S. Rep. No. 90-1097, at 66 (1968), as reprinted in 1968

U.S.C.C.A.N. 2153)). It follows, then, that "wiretapping is to be

distinctly the exception — not the rule." United States v.

Hoffman,

(1st Cir. 1987).

To ensure that the exception does not swallow the rule,

the law "imposes a set of statutory requirements on top of the

constitutional requirements applicable to ordinary search

warrants." United States v. Burgos-Montes,

(1st

Cir. 2015). Of particular pertinence for present purposes, the

wiretap application must contain (in addition to the foundational

showing of probable cause) "a full and complete statement as to

whether or not other investigative procedures have been tried and

failed or why they reasonably appear to be unlikely to succeed if

tried or to be too dangerous." United States v. Nelson-Rodriguez,

(1st Cir. 2003) (quoting

(1)).

"This aptly-named 'necessity' prong requires the government to

have 'made a reasonable, good faith effort to run the gamut of

normal investigative procedures before resorting to means so

intrusive as electronic interception of telephone calls.'" Rose,

- 8 -

(quoting United States v. Cartagena,

(1st Cir. 2010)).

Of course, necessity is "a relative term — and it is

context-specific." Gordon,

. Necessity must,

therefore, "be viewed through the lens of what is pragmatic and

achievable in the real world."

. This is particularly

true in cases — like this one — that involve large, complex drug-

trafficking networks: "[b]ecause drug trafficking is inherently

difficult to detect and presents formidable problems in pinning

down the participants and defining their roles, investigative

personnel must be accorded some latitude in choosing their

approaches." United States v. David,

(1st Cir.

1991).

In the case at hand, the government pinned its hopes for

a wiretap authorization on an affidavit executed by Michael P.

Boyle, a DEA special agent.2 The defendants challenge the adequacy

of this affidavit as a means of demonstrating necessity. Although

their challenge is multi-dimensional, their central thesis is that

the government gave short shrift to traditional investigative

procedures and sought to resort to wiretap surveillance with

2 At the time he submitted the affidavit, Boyle had been a DEA special agent for over twenty-four years and had served as the case agent for numerous high-priority drug and gang cases. In his own words, he had received "hundreds of hours of additional specialized training in narcotics law enforcement, including courses in drug trafficking, criminal enterprises and gangs."

- 9 - precipitous haste. The district court rejected this thesis,

determining that the government "made a reasonably good faith

effort to run the gam[ut] of normal investigative procedures before

resorting to electronic surveillance."

We begin with bedrock: the Supreme Court has warned

that a wiretap is "not to be routinely employed as the initial

step in criminal investigation." United States v. Giordano,

(1974). Even so, "the government need not

demonstrate that it exhausted all investigative procedures" before

turning to a wiretap. Santana, 342 F.3d at 65. To strike this

balance, a reviewing court must examine whether reasonable

procedures were attempted (or at least thoroughly considered)

prior to seeking a wiretap. See United States v. Lopez,

(1st Cir. 2002). Relatedly, the court must examine the

need for a wiretap in light of what those procedures yielded. See

United States v. Delima,

(1st Cir. 2018).

The defendants counter that the government made a

gadarene rush to employ electronic surveillance and that, as a

result, its attempt to show necessity is unconvincing. Here,

however, the district court supportably determined that Boyle's

affidavit was sufficient to allay any reasonable concern that the

wiretap was being sought prematurely. The affidavit demonstrated

that the government had employed (and exhausted) a number of

traditional investigative measures over the course of more than

- 10 - six months, which included obtaining information from confidential

sources and informants; conducting protracted physical

surveillance; participating in controlled drug buys; issuing

administrative subpoenas for telephone, rental car, and travel

records; and analyzing telephone records and pen register data.

The district court found that nothing in Boyle's affidavit, fairly

read, suggested an effort on the government's part to shortcut

normal procedures. This finding easily passes muster under clear

error review.

Next, the defendants assert that the affidavit

demonstrated the opposite of what the government intended. Rather

than showing that the procedures employed to that point had failed

to achieve the goals of the investigation, the affidavit — as

Santana-Dones says in his brief — is a testament to the

government's "great investigative success by traditional

investigative means." He adds that the government "had more than

enough 'goods' to pursue criminal prosecution but instead wanted

to get to bigger fish." Seen in this light, the defendants

contend, the more intrusive wiretap procedure was not necessary.

The district court rejected this contention, and so do

we. The inquiry into whether the government has sufficiently

demonstrated necessity does not hinge on whether it already has

garnered enough goods to pursue criminal prosecution. After all,

an application for a wiretap will always have to disclose some

- 11 - meaningful level of previous success in order to satisfy the

probable cause requirement and justify further investigation. See

Rose,

n. 1; Nelson-Rodriguez,

.

Thus, the inquiry must be directed to whether traditional

investigative procedures already have succeeded or would be likely

to succeed in laying bare the full reach of the crimes that are

under investigation. See Delima,

; Villarman-Oviedo,

. If not, the government may be able — as here — to

show the need for a wiretap in order to complete its investigation.

See Rose,

(holding that some level of success in

investigation did not foreclose a finding of necessity when "the

government was still seeking a wealth of information at the time

that it submitted the wiretap applications").

To be sure, the level of success achieved through a given

procedure will vary in relation to the scope of the investigation

as established by the government. It follows that, in seeking a

wiretap, the government cannot be permitted to set out goals that

are either unrealistic or overly expansive. See Delima,

. Placing a judicial imprimatur on such a tactic would allow

the government to characterize any level of success as incomplete

and, thus, to portray a wiretap as necessary in virtually every

circumstance. See United States v. Blackmon,

(9th Cir. 2001) ("The government may not cast its investigative

- 12 - net so far and so wide as to manufacture necessity in all

circumstances.").

Here, however, the government's stated investigatory

goals mirror those that we have sanctioned in earlier wiretap

cases. The government's brief summarizes those goals as including

"discovering the sources, delivery means, storage locations, and

distribution methods for the narcotics; locating resources used to

finance the trafficking; and determining how the conspiracy

invested and laundered their drug proceeds." The district court

implicitly found these goals, which focused on locating

distribution sources and tracking funds, both reasonable and

attainable.

Information such as the government sought by means of

the proposed wiretap is meat and potatoes in a drug-trafficking

investigation, not pie in the sky. This helps to explain both why

the stated goals of the investigation appear reasonable and

attainable and why we conclude that the district court's implicit

finding was not clearly erroneous. And in so concluding, we do

not write on a pristine page. For instance, we held in Delima

that the government's investigatory goals were not overly broad

when the government sought to "(1) identify the conspiracy's

leaders; (2) ascertain the names, phone numbers, and addresses of

associates of the conspiracy, including drug suppliers,

distributors, and customers; (3) determine the manner in which

- 13 - drugs were trafficked [] and stored . . . ; and (4) discover the

methods used by the organization to funnel proceeds back to

individual participants."

. So, too, in United

States v. Martinez, we identified as "discrete and realistic goals

for a criminal drug investigation" the government's stated

objectives of identifying drug suppliers, discerning the manner in

which the organization transported drugs, establishing how

payments were made, pinpointing storage locations, and

understanding how the coconspirators laundered and invested drug

proceeds.

(1st Cir. 2006).

The district court also found that the government's

affidavit described a level of success through traditional

procedures that fell short of meeting these "legitimate and

attainable" goals.

. This finding, too, passes muster

under clear error review. We hold, therefore, that the

government's successful use of traditional investigative tools up

to the date of Boyle's affidavit does not defenestrate its showing

of necessity. See United States v. Cao,

(1st Cir.

2006) ("Plainly the partial success of the investigation did not

mean that there was nothing more to be done." (emphasis in

original)).

The defendants launch yet another attack on the

government's showing of necessity. They say that the government

did not sufficiently demonstrate the failure, futility, or danger

- 14 - of traditional investigative procedures. Their argument rests

heavily on the fact that one of the government's confidential

sources, who previously had engaged only in controlled drug buys,

was invited to work directly for the drug-trafficking organization

but refused on the government's instructions. Building on this

foundation, the defendants maintain that Boyle's affidavit "never

establishe[d] with any logic" why the DEA failed to avail itself

of this opportunity to penetrate the drug ring. Moreover, the

defendants insist that the government presented no evidence of any

likely danger.

Like the district court, we review the government's

assessment that a specific investigative opportunity is overly

dangerous or unlikely to be productive in a "practical and

commonsense manner." Hoffman,

(quoting United

States v. Scibelli,

(1st Cir. 1977)). Here,

some of the statements contained in Boyle's affidavit are based,

at least in part, upon his experience as a specially trained agent.

"We have regularly upheld affidavits in support of wiretap

applications where the agents assert a well-founded belief" that

traditional investigative procedures had run their course and that

further use of them would likely prove futile in achieving the

goals of the investigation. Rodrigues,

. So, too,

where the agents assert a well-founded belief that traveling down

- 15 - a particular investigative avenue would be too dangerous. See,

e.g., Ashley,

.

Viewed against this backdrop, it is evident that the

mere existence of an opportunity for a government cooperator to

take a more prominent position in the targeted enterprise does not

automatically render a wiretap unnecessary. United States v.

Woods,

(6th Cir. 1976), illustrates this point.

There, a government informant had declined an invitation to become

a "lieutenant" in the enterprise under investigation.

.

The defendant moved to suppress subsequently gathered wiretap

evidence on the basis that the government turned down this

invitation. The district court denied the motion, and the Sixth

Circuit affirmed, stating that the informant's opportunity to

"penetrate deeper into a criminal organization under

investigation" did not in any way undermine the government's

showing of necessity.

Boyle's affidavit struck a similar tone. In it, he

highlighted several potential pitfalls. He first reasoned that

even if the confidential source became a member of the drug-

trafficking organization, she was unlikely to gain access to needed

"information such as the identity of the source of supply, the

methods of delivery or the intended transportation route, or the

larger distribution network." In support, Boyle noted the high

degree of compartmentalization that characterized the drug-

- 16 - trafficking organization and what would be the source's entry-

level status. Based on these representations — which comprise

appreciably more than "conclusory statements that normal

techniques would be unproductive," Ashley,

— the

district court concluded that the government sufficiently showed

that the proposed infiltration would in all probability be futile

as a means of achieving certain goals of the investigation and,

thus, did not obviate the necessity for a wiretap. This finding

is not clearly erroneous.

If more were needed — and we doubt that it is — the

district court also gave weight to Boyle's expressed concern that

an attempt to infiltrate the organization could backfire and

jeopardize the entire investigation. Boyle's affidavit

persuasively predicted a greater likelihood of exposure should an

infiltration be attempted, emphasizing the wariness of members of

the drug ring and the fact that the government's other confidential

source had already been compromised. Given these concerns, we

discern no clear error in the district court's determination that

the risk of exposure reinforced the government's decision not to

try the infiltration gambit before seeking a wiretap.3

3 In a related vein, the district court concluded that pursuing infiltration of the drug-trafficking organization was apt to be too dangerous. The court based its conclusion on the inherent perils of asking a government cooperator to work undercover for a large drug-trafficking organization and the risk of discovery. Even though Boyle's affidavit was not specific on

- 17 - In sum, the limited prospect of advancing the

investigation's goals, the potential jeopardy to the confidential

source, and the risk of exposing the investigation coalesced to

provide a firm basis for the district court's conclusion that the

game was not worth the candle. It follows inexorably, as night

follows day, that the opportunity to infiltrate did not render the

proposed wiretap unnecessary.

That ends this aspect of the matter. We hold that the

district court did not err in concluding that the wiretap

application, read in tandem with its supporting affidavit, was

more than minimally adequate to justify the authorization of a

wiretap. Consequently, we reject the defendants' unified claim of

error.

this score — it stated, in conclusory terms, only that the government feared that an attempt to infiltrate the organization would "pose a serious risk to the personal safety" of the confidential source — the status and circumstances of the investigation justified a reasoned belief that the proposed infiltration was fraught with danger. See Gonzalez, 412 F.3d at 1115 ("Quite sensibly, the necessity requirement for a wiretap order does not compel law enforcement officers to use traditional investigative strategies at the risk of danger to themselves or others."); United States v. Smith,

(4th Cir. 1994) (affirming district court's finding that infiltration was "too dangerous to be a reasonable option"); see also United States v. Mills,

(1st Cir. 2013) (stating that "snitching is dangerous work, and informants literally put their lives on the line by doing what they do").

- 18 - III. THE REMAINING CLAIMS.

Vasquez — who is represented in this court by yet another

counsel — advances two more claims of error. First, he submits

that the district court erred in denying his motion for an

extension of time within which to file additional motions to

suppress. Second, he submits that certain of his prior lawyers

(Counsel 2A, 2B, and 3) abridged his Sixth Amendment right to

effective assistance of counsel. We discuss these claims of error

sequentially.

A. Extension of Time.

Court-imposed deadlines are often used to ensure the

orderly administration of justice — and quite properly so. In

federal criminal cases, district courts typically set such

deadlines for the filing of pretrial motions. This practice is

memorialized in Federal Rule of Criminal Procedure 12(c)(1), which

provides in pertinent part that a district court may, in its

discretion, "set a deadline for the parties to make pretrial

motions." The court may enlarge or revise such a deadline at any

time before trial. See Fed. R. Crim. P. 12(c)(2).

When a party seeks to file a pretrial motion out of time,

the district court may, upon a showing of "good cause," grant such

a motion. Fed. R. Crim. P. 12(c)(3). This good cause standard

gives Rule 12(c) some bite, underscoring the district court's

authority to set and enforce motion-filing deadlines. Cf. United

- 19 - States ex. rel. D'Agostino v. EV3, Inc.,

(1st

Cir. 2015) (discussing civil analogue to Rule 12(c)). We review

a district court's decision to deny relief under Rule 12(c)(3)

solely for abuse of discretion. See United States v. Arias,

(1st Cir. 2017); United States v. Santos Batista,

(1st Cir. 2001).

We move now from the general to the specific. Early on,

the parties in this case filed a joint memorandum, see D. Mass. R.

116.5(c), setting a June 13, 2016, deadline for filing pretrial

motions to suppress. The district court acquiesced in this

deadline, and the defendants twice obtained judicial extensions of

it. The latest version of the deadline expired on July 18, 2016.

By then, the defendants had filed their joint motion to suppress

the wiretap evidence. See supra Part II.

The district court denied the joint suppression motion

on October 11, 2016. Vasquez's lawyers (Counsel 2A and 2B)

withdrew shortly thereafter. They were succeeded by Counsel 3,

who served in that capacity for less than a month and withdrew on

December 5, 2016. Three days later, the district court appointed

Counsel 4 to represent Vasquez.

On January 3, 2017, Counsel 4 moved for a 90-day

extension of time within which to file a motion to suppress.

Counsel 4 indicated that Vasquez wished to file a motion to

suppress evidence obtained from the search of his home and

- 20 - "possibly" another motion to suppress wire communications. In a

hearing on the motion to extend, Counsel 4 doubled down, stating

that Vasquez also wished to move to suppress the fruits of the GPS

tracking warrant.

Because Vasquez's motion for an extension effectively

sought leave to file untimely motions, it directly implicated Rule

12(c)(3)'s good cause standard. See United States v. Sweeney,

(1st Cir.), cert. denied,

(2018). We

have interpreted the good cause standard to require a showing of

both cause (that is, a good reason for failing to file a motion on

time) and prejudice (that is, some colorable prospect of cognizable

harm resulting from a failure to allow the late filing). See

Arias,

; Santos Batista,

. "Such a

showing is, by its very nature, fact-specific." United States v.

Ayer,

(1st Cir. 1988).

In the court below, Vasquez's attempt to show good cause

consisted of characterizing his prior lawyers as either too busy

to file timely motions or simply guilty of dereliction of duty.

For example, he suggested that Counsel 2A and 2B "surely spent the

bulk of [their] time reviewing the voluminous related discovery

and preparing the very well-crafted motion and memorandum" on the

wiretap suppression motion and, thus, did not have enough time to

file other motions to suppress. He surmised that Counsel 2A and

2B would have filed these additional motions if they had more time,

- 21 - and that their failure to file these motions indicated some

irredeemable flaw in their representation.

The district court rejected Vasquez's speculative

arguments, finding that Counsel 2A and 2B had "ample opportunity

to prepare and present the issues," especially since the relevant

deadline had been suggested by the defendants and twice extended

by the court. The district court further found that Vasquez had

been represented by "experienced, able and qualified" attorneys

and that he could not "avail himself of a 'do over' [simply]

because he ha[d] successor counsel."

We detect nothing resembling an abuse of discretion in

the district court's conclusion that Vasquez failed to demonstrate

good cause for reopening the motion-filing deadline over five

months after it had expired. Good cause for allowing a defendant

to file motions out of time demands more than the appearance of

new counsel seeking to second-guess the decisions of prior counsel.

See United States v. Trancheff,

(8th Cir. 2011).

After all, allowing new counsel to reopen an expired deadline in

order to pursue strategic options forgone by prior counsel would

put a premium on changing counsel and unfairly advantage the

defendant.

Nor is there any basis for a claim that Vasquez was

subjected to unreasonable temporal constraints. His then-counsel

participated in the setting of the original deadline for filing

- 22 - motions to suppress, and the district court twice obliged the

defendants (including Vasquez) when they sought to enlarge this

deadline. All told, Vasquez had a total of 297 days from the date

of his arraignment until the expiration of the extended deadline

within which to file pretrial motions. That was ample time for

his counsel to prepare and file any strain of suppression motion.

To say more about this claim of error would be pointless.

We conclude, without serious question, that the district court

acted well within the wide encincture of its discretion in denying

Vasquez's motion to extend.

B. Ineffective Assistance of Counsel.

Vasquez also argues that several of his prior lawyers

(namely, Counsel 2A, 2B, and 3) were constitutionally ineffective

in representing him. See U.S. Const. amend. VI; see also

Strickland v. Washington,

(1984). This claim of

error, though, was not adjudicated in the district court. While

Vasquez's motion to extend alleged that ineffective assistance of

counsel was one of the reasons explaining the untimeliness of the

motion, he did not make a Sixth Amendment claim at that time.

Consequently, no attempt was made to develop a record that might

be suitable for the adjudication of such a claim.

"We have held with a regularity bordering on the

monotonous that fact-specific claims of ineffective assistance

cannot make their debut on direct review of criminal convictions,

- 23 - but, rather, must originally be presented to, and acted upon by,

the trial court." United States v. Mala,

(1st

Cir. 1993). In adopting this prudential praxis, we have reasoned

that "such claims typically require the resolution of factual

issues that cannot efficaciously be addressed in the first instance

by an appellate tribunal."

More particularly, "'why counsel

acted as he did [is] information rarely developed in the existing

record,' and this information is crucial to resolve an ineffective

assistance claim." United States v. Vázquez-Larrauri,

(1st Cir. 2015) (emphasis and alteration in original)

(quoting United States v. Torres-Rosario,

(1st

Cir. 2006)). Unless "the critical facts are not genuinely in

dispute and the record is sufficiently developed to allow reasoned

consideration" of a claim of ineffective assistance, a criminal

defendant who wishes to pursue such a claim must do so in a

collateral proceeding. United States v. Natanel,

(1st Cir. 1991).

Apparently mindful that, over the years, we have

resolutely hewed to this principle, see, e.g., United States v.

Miller,

(1st Cir. 2018); United States v.

Kifwa,

(1st Cir. 2017); United States v. Torres-

Estrada,

(1st Cir. 2016), Vasquez struggles to

bring his case within the narrow confines of the Natanel exception.

He suggests, based primarily on the assessment of Counsel 4, that

- 24 - the additional motions to suppress had such obvious merit that the

failure to file them within the allotted time frame was

unquestionably a grave mistake. The premise on which this

suggestion rests is sound: the Natanel exception might apply if

the record was sufficiently developed to demand a conclusion that

the failure to file the additional suppression motions was

"objectively unreasonable 'under prevailing professional norms.'"

United States v. Mercedes-De La Cruz,

(1st Cir.

2015) (quoting Strickland,

). But this is not such

a case.

The searches at issue here were conducted pursuant to

duly issued warrants, so that a court, in each instance, had made

a preliminary determination of probable cause. Moreover, we have

no way of telling, on this incomplete record, why Vasquez's prior

counsel did not file such motions. The rule of Occam's Razor

teaches that the simplest of competing theories should often be

preferred and, here, the obvious reason — that counsel simply did

not believe that the motions would succeed — is entirely plausible.

In a nutshell, the record simply does not justify a finding that

counsel's failure to file additional motions to suppress was

objectively unreasonable under prevailing professional norms.

The short of it is that the relevant facts have not been

adequately developed. And, thus, Vasquez's ineffective assistance

- 25 - of counsel claim falls squarely within the Mala rule. We therefore

dismiss this claim of error without prejudice.

IV. CONCLUSION.

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

we affirm the judgments of the district court; without prejudice,

however, to Vasquez's right to raise his ineffective assistance of

counsel claim, should he so elect, in a collateral proceeding

pursuant to

.

So Ordered.

- 26 -