United States Court of Appeals For the First Circuit

No. 22-1723

UNITED STATES,

Appellee,

v.

DANIEL DONALD,

Defendant, Appellant.

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

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

Before

Barron, Chief Judge, Howard and Gelpí, Circuit Judges.

Michael Pabian, for appellant.

Karen L. Eisenstadt, Assistant United States Attorney, with whom Rachael S. Rollins, United States Attorney, was on brief, for appellee.

October 16, 2023 BARRON, Chief Judge. This appeal concerns the challenge

that Daniel Donald brings to his five 2021 convictions in the

United States District Court for the District of Massachusetts on

federal drug- and gun-related charges. He argues that the

convictions must be vacated because the District Court failed to

suppress incriminating statements that he made to law enforcement

which he contends were obtained in violation of his rights under

Miranda v. Arizona,

(1966). We agree.

I.

A.

A federal grand jury returned the operative indictment

in May 2019. It charged Donald with conspiracy to distribute and

to possess with intent to distribute heroin, cocaine, cocaine base,

and fentanyl in violation of

(Count One);

possession with intent to distribute those drugs in violation of

(a)(1) (Counts Two through Five); and being a felon

in possession of a firearm in violation of

(g)(1)

and 924(e) (Count Six). Before trial, Donald moved to suppress

statements that he made to law enforcement immediately after his

arrest, which occurred on November 30, 2017.

At the evidentiary hearing on the suppression motion,

the government called only one witness -- Gary Morris, a Worcester,

Massachusetts police officer who was a member of a U.S. Drug

- 2 - Enforcement Agency Task Force ("Task Force") that had been

investigating Donald for his suspected involvement in a drug-

distribution operation. Officer Morris testified as follows.

On November 30, 2017, Task Force members executed

federal search warrants in Worcester at a basement apartment and

an adjacent, detached apartment, each of which Donald was renting.

Although Donald did not live in either apartment, the Task Force

suspected that he and two other individuals were using the

apartments to run a drug-distribution operation.

On the day of the search, Donald arrived at the property

where the two apartments were located accompanied by the two other

individuals. Task Force members then detained the three of them,

took them inside the basement apartment, and showed them the

federal search warrants. One of the Task Force members thereafter

recited Miranda warnings to the three individuals, including

Donald, and presented them with a pre-printed form to sign titled

"Miranda Warnings and Waiver."

The form included questions regarding whether the three

individuals understood their Miranda rights as well as whether

they wished to waive those rights and speak to investigators.

Donald signed the form and did not place a checkmark on the line

next to the statement that read: "Yes, I wish to talk to you now

and waive my Fifth Amendment Right pursuant to Miranda."

- 3 - Members of the Task Force proceeded to execute the search

warrants. Inside the basement apartment, the Task Force members

found two grinders of the type that can be used to grind and dilute

drugs. In the detached apartment, the Task Force members found -

- hidden in a wall -- a kilogram of cocaine, 345 grams of heroin,

80 grams of crack cocaine, 200 fentanyl pills, and a loaded

firearm.

Officer Morris returned to the basement apartment and

spoke with a DEA agent on the scene about the contraband that had

been found in the detached apartment. At that point, Donald

approached members of the Task Force and asked to speak with "the

bald guy," which the Task Force members understood to be a

reference to DEA Agent David DiTullio.

Officer Morris and Agent DiTullio took Donald to the

bathroom of the basement apartment to speak privately. While

there, Officer Morris "reminded" Donald of the Miranda warnings

that Donald had been given. Donald "stated he wished to speak to"

Task Force members, "asked what he can do to help himself," and

stated that "he would provide information."1 Agent DiTullio then

Agent DiTullio later testified at trial that Donald did not 1

at that time state the purpose of his request to speak. However, because Donald agrees that we must assess the record "in the light most favorable to the trial court ruling," United States v. Tibolt,

(1st Cir. 1995), we accept Officer Morris's testimony on this point for the purposes of the analysis below.

- 4 - responded that any further conversation would have to occur at the

Worcester Police Department ("WPD"). No further conversation with

Donald occurred at the property.

Task Force members transported Donald to the WPD, where

he affirmed that he still wished to speak to law enforcement.

Donald was escorted to a room that was being both audio and video

recorded. We recount below what the parties agree that recording

establishes, noting any points of dispute along the way.

At the WPD, Officer Morris first reminded Donald of his

Miranda rights by stating:

I'm just gonna remind you that at the house I Mirandized you, read you your rights, you understood those right. . . . [Y]ou signed the form saying you understood them. . . . [E]verything's still the same and . . . you know if you wish to talk with us, if you want to stop at any time that's your right to do so. After that, Agent DiTullio began speaking to Donald, stating:

So as we talked before, . . . we're going down the road of the state charges tonight . . . this could have went another way, but you have some information that may help you with this whole thing. . . . And based on that, we're willing to talk to you . . . . So . . . we showed our hand of good faith by . . . you're not being charged federally tonight. Soon thereafter, Agent DiTullio asked Donald, "You know

what we got out of the side of the house, you know exactly what

- 5 - was there, right?" Donald then paused, put his hands in the air,

and asked, "None of this can be used against me, can it?"

The parties do not agree about what happened next.

Donald contends that Officer Morris answered the question that

Donald had asked by saying, "No." The government argues that the

record supportably shows that Officer Morris did not provide that

answer or, at least, that it supportably shows that he did not do

so in any "intelligible" manner.

The parties do agree, however, that whether or not

Officer Morris responded "No" to Donald's question, Agent DiTullio

stated right after that question: "We have the stuff so it's, so,

it is what it is . . . ." The parties further agree as to the

following sequence of events.

Donald interrupted Agent DiTullio and stated, "I

understand so that's just, yes let's just . . . yes ok yes sure I

assumed. Just ok so go ahead, so you got what you got and what

can I do to help myself out is what I want to get to." Agent

DiTullio responded to Donald's interruption by asking him to "tell

[them] the story" because this was "the first step in cooperation"

and that he should "tell [them] . . . what [he] kn[e]w was in the

side of the house" because "[they] kn[e]w what was there." Donald

sighed and chuckled, after which Agent DiTullio said, "You gotta

- 6 - trust us man. Like we told you, not 92% cooperation not 99, you

gotta be on board and trust us."

Donald responded:

I understand that, you know, but I'm trying to do what I can to get myself out of a bad situation. I know that I can guarantee to you guys, but on your end, you can't guarantee much of anything outside of the fact that you know, "you help us out, we'll do what we can." I don't want to put myself under the . . . gun giving statements . . . of what was there, so on and so forth, and it gets held against me in the court of law as evidence. You know what I'm saying? I know what . . . you guys got but you have to prove that it's mine. And we're not going to do that, okay, I'm just simply saying I know what . . . was there and I wanna do what I can to help myself out . . . . Officer Morris stated at that point that the Task Force

was "starting with" "keeping the charges at the state level" if

Donald was "willing to cooperate," to which Donald replied, "I

am." Donald then stated: "[H]ypothetically speaking, let's say

there was a kilo of coke, a little over 300 grams of dopy and a

little over 200 pills and whatever, hypothetically . . . and a

gun, hypothetically." Agent DiTullio and Officer Morris then

continued asking Donald questions about what was in the house.

Later, Officer Morris told Donald that for him to be

able to form a "partnership" with members of the Task Force, Donald

would have to "show something . . . of what [he could] do to help

- 7 - [them]." Donald proceeded to give a full confession over the

following twenty minutes regarding the nature and extent of his

drug-dealing activities, the identity of his supplier, and how and

when Donald might be able to arrange a meeting with that supplier

so that officers could apprehend that supplier. Donald was charged

the next day with the federal crimes set forth in the operative

indictment.

B.

Prior to trial, Donald moved to suppress "all" the

statements that he made "on November 30th, 2017." The District

Court denied Donald's motion to suppress in a written order on May

23, 2019.

In doing so, the District Court rejected Donald's

contention in his motion that Officer Morris responded "No" when

Donald asked, "None of this can be used against me, can it?" The

District Court found, based on its review of the recording of the

interrogation, that Officer Morris did not so respond and that

"[i]f there was a response . . . it was unintelligible."

Donald moved for reconsideration of this ruling, but the

District Court denied the motion. The case then proceeded to

trial.

During the cross-examination of Agent DiTullio, Donald's

counsel played the recording and asked Agent DiTullio, "Did you

- 8 - hear officer -- Task Officer Morris say any communication on the

video?" Agent DiTullio responded, "He said 'no.'" Counsel then

said, "Okay. So to the -- what you call to be a response, can any

of this be used against me, you -- and after that statement was

made, you heard Task Officer Morris say no?" Agent DiTullio

responded, "Yes."

Based on the testimony from Agent DiTullio, Donald

orally moved at the close of the government's case for the District

Court to reconsider its suppression ruling. Donald did so again

at the close of evidence.

The District Court denied both motions. The jury

returned its verdict on October 29, 2021, and found Donald not

guilty of the conspiracy charge (Count One) but guilty of the

remaining charges (Counts Two through Six).

A few weeks later, on November 17, 2021, the District

Court noted during a teleconference between the parties that it

had some concerns about its suppression ruling due to Agent

DiTullio's testimony. Donald subsequently filed his fourth motion

for reconsideration of the denial of his suppression motion. The

District Court heard argument on the matter on June 23, 2022.

Donald addressed the District Court directly at that time and

stated:

I was under the impression that my statements were not going to be used against me for a

- 9 - variety of reasons. . . . [T]he interrogation began under the premise where Agent DiTullio was representing to me that I was there to help myself out . . . . Again, I attempt to make clear what my position is that I don’t want to give statements about what was discovered in the hide and have those statements used against me in a court of law as evidence. . . . So, although I didn’t feel comfortable speaking about the gun and the drugs, I didn’t necessarily have a problem in the confession, because I was under the impression . . . I was there to help myself out, that my cooperation would result in me not being charged federally . . . . Again, I took that interpretation to mean that my previously invoked rights were the same as everything else, and I could speak freely with them, because it was in the -- in a form of a cooperation. So while there’s no disagreement that I generally understood what my rights were, I do believe that in certain context on certain situations an individual can provide statements without the worry of having those statements come back to haunt them, such as, I don’t know, maybe in a proffer session or something like that.

On July 29, 2022, the District Court issued a written

order that denied Donald's fourth motion for reconsideration. The

District Court concluded, as it had in its earlier rulings on the

suppression motion, that Donald understood his Miranda rights and

"knowingly, intelligently and voluntarily waived them, and agreed

to talk to the agents."

The District Court also assessed whether statements that

Donald made in the recording "constituted his free and voluntary

- 10 - act." It concluded that, despite Agent DiTullio's testimony that

he heard Officer Morris respond "No" to Donald's question, it still

could not "determine that [Officer Morris] said 'No,'" mainly

because Donald "did not wait for the agents to respond before he

started to make statements, thereby undermining his contention

that he only talked to the agents because of the assurance that

his statements could not be used against him." The District Court

did not stop there, however. It also concluded that, even if

Officer Morris did say "No," it was "not clear whether [Officer

Morris] was assuring Donald that his statements could not be used

against him," and Donald "never asked for clarification" and never

"again raise[d] the issue of whether anything he [said could] be

used against him." The District Court further reasoned that

Donald's conduct later in the interview, such as speaking in

hypotheticals, "create[d] a strong inference that Donald

understood anything he said could be used as evidence against him

at trial." And, additionally, the District Court pointed to

Donald's "significant criminal history" and "experience[] with the

criminal justice system," as well as the fact that he initiated

the interview, as reasons to think that Donald's responses were

voluntary.

Thus, the District Court found "[b]ased on the totality

of the circumstances . . . that Donald did not misunderstand his

- 11 - rights" and "knew that any statements made to [Agent DiTullio] and

[Officer Morris] could be used against him at trial." In addition,

the District Court found in "making this determination" that

"neither [Agent DiTullio] or [Officer Morris] made any assurance

to Donald that his statements could not be used against him such

that his statements were rendered involuntary or otherwise

undermine the effectiveness of the Miranda warnings which had been

given."

The judgments of conviction, per which Donald was

sentenced to 192 months of imprisonment, were entered on September

14, 2022. Donald then filed this timely appeal.

II.

We begin with the portion of Donald's challenge to his

convictions in which he contends that the government failed to

show that he validly waived his Miranda rights before he made the

statements that he seeks to suppress. One of his arguments in

that regard rests on the contention that the District Court clearly

erred in finding that Officer Morris did not respond "No" to

Donald's question "None of this can be used against me, can it?"

Donald reasons that any Miranda waiver that he supposedly made

could not have been valid if that "waiver" came only after Officer

Morris responded "No." Donald contends that any such waiver then

would have been the result of law enforcement's misdescription of

- 12 - the waiver's consequences and so could not have been knowingly,

intelligently, and voluntarily made.

As we will explain, we conclude that the District Court

clearly erred in finding that Officer Morris did not respond "No"

and that, reviewing de novo, the "No" response rendered Donald's

purported Miranda waiver invalid. Accordingly, we begin and end

our analysis of Donald's challenge to his convictions on those

grounds,2 as we see no basis for concluding that the District

Court's denial of Donald's suppression motion was harmless error.

A.

There are "two distinct dimensions," Moran v. Burbine,

(1986) (citing Edwards v. Arizona,

(1981)), to the inquiry into whether a Miranda waiver was

"voluntarily, knowingly and intelligently" made. Miranda,

. First, "the relinquishment of the right must

have been voluntary in the sense that it was the product of a free

and deliberate choice rather than intimidation, coercion, or

deception." Moran,

. Second, "the waiver must

2Donald separately argues that we must reverse the District Court's denial of his motion to suppress because the interrogators did not "scrupulously honor[]" his express invocation of his right to remain silent under Miranda, as required by Michigan v. Mosley,

(1975). And that is so, Donald argues, because the interrogators did not give him a fresh set of Miranda warnings at the outset of the interview. We do not address that contention because we conclude that the government cannot satisfy its burden to show that Donald validly waived his Miranda rights.

- 13 - have been made with a full awareness of both the nature of the

right being abandoned and the consequences of the decision to

abandon it."

Thus, "[o]nly if the 'totality of the

circumstances surrounding the interrogation' reveal both an

uncoerced choice and the requisite level of comprehension may a

court properly conclude that the Miranda rights have been waived."

(quoting Fare v. Michael C.,

(1979)).

The government "bears the burden of showing the validity

of the waiver by a preponderance of the evidence," and we must

"start with a presumption that [Donald] did not waive his rights,"

United States v. Carpentino,

(1st Cir. 2020). To

determine whether the government has met its burden to show that

a valid waiver occurred, we review de novo "determinations on

matters of law, including whether the totality of the circumstances

demonstrate that the defendant's statement was knowing and

voluntary." United States v. Rojas-Tapia,

(1st Cir.

2006). We review "subsidiary findings of fact" for clear error.

B.

The parties agree that Donald expressly invoked his

Miranda rights when he declined to speak to law enforcement after

he was given the "Miranda Warnings and Waiver" form. There also

is no dispute that Donald did not expressly waive those rights at

- 14 - any time thereafter. The question, then, is whether he impliedly

did so.

Donald conceded at oral argument that if he impliedly

did so before he asked, "None of this can be used against me, can

it?" then he would likely have no claim under Miranda, given our

ruling in United States v. Bezanson-Perkins,

(1st

Cir. 2004). But the government does not contend in its briefing

to us that the asserted implied waiver occurred before Donald asked

that question or even before Officer Morris responded to it,

insofar as Officer Morris did so respond. Indeed, the government

states in its briefing to us that Donald "waived his Miranda rights

by participating in the interview that he himself had requested"

(emphasis added). And we do not understand the government in so

stating to be suggesting that Donald's mere asking of the question

that preceded the supposed "No" response from Officer Morris

amounted to Donald "participating in the interview" that followed.

Nonetheless, the government did contend for the first

time at oral argument that Donald waived his Miranda rights when

he first indicated (after having invoked Miranda) that he wanted

to speak to law enforcement and that he then waived those rights

again at the WPD at some point before Donald argues that Task Force

Officer Morris answered "No." But we see no merit to this late-

breaking contention.

- 15 - As an initial matter, we note that we do not understand

the District Court to have found that Donald's waiver of his

Miranda rights occurred either before Donald asked the question to

Officer Morris that precipitated the claimed "No" response or

before the moment at which Donald contends that Officer Morris

responded "No." For, in denying Donald's first motion to suppress,

the District Court did not determine that the waiver occurred at

the property where the searches were executed based solely on

Donald having reinitiated communication with law enforcement after

having expressly asserted his Miranda rights. Rather, the District

Court found that there had been a waiver, not only based on the

fact that Donald was reminded of Miranda at the outset of the

interview at the WPD, but also based on the fact that the recording

of the interview "reflects a free-flowing exchange initiated by

the Defendant with the agents." Similarly, in the denial of

Donald's motion for reconsideration of the denial of the

suppression motion, the District Court rested its determination

that there had been a valid waiver on the course of the "free-

flowing exchange" as a whole -- that is, on statements that Donald

made throughout the exchange and on the fact that law enforcement

made no assurances to him during the exchange that could "undermine

the effectiveness of the Miranda warnings which he had been given."

- 16 - In any event, our precedents preclude us from agreeing

with the government's belated contention about how early the

claimed waiver occurred. The record does show that Donald

initiated contact with Task Force members at the property where

the searches were executed after he had expressly invoked his

Miranda rights. But we have explained that "[a] suspect does not

waive his Miranda rights merely by initiating investigation-

related communication with law enforcement officers after

previously asserting his right to counsel." Carpentino,

. And we see no basis in the record for concluding that,

after having expressly invoked his Miranda rights, Donald did more

than initiate investigation-related communication with law

enforcement prior to making the statements that followed what

Donald contends was the "No" response from Officer Morris.

In Carpentino, for example, we held that the defendant

had not waived his Miranda rights, after having expressly invoked

them, by waving from his cell to get a guard's attention, asking

to talk to the troopers who had previously interviewed him,

returning to an interview room, and responding once there to a

trooper's statement that the troopers would "have to re-Mirandize

[him] because [they] brought [him] back in" by stating: "How much,

would, uhm, the maximum time be for something like this?"

. Instead, we concluded that the waiver had occurred based on

- 17 - what happened "[a]fter the defendant initiated the second phase of

the interview."

(emphasis added).

The government is right that in United States v. Mejia,

(1st Cir. 2010), we stated that there are "certain

types of cases in which courts routinely conclude that a defendant

who has professed an understanding of his right to remain silent

has waived that right" and that these include cases where "after

receiving warnings and asserting . . . a right to remain silent,

[the defendant] spontaneously recommences the dialogue with his

interviewers,"

. But Mejia is fully consistent with

Carpentino in determining the validity of asserted waiver by

focusing on what had occurred over the course of the defendant's

"dialogue" with officers, and not simply on what had occurred at

the moment at which the defendant chose to initiate communication

with law enforcement.

Indeed, in concluding that there was

a valid Miranda waiver in Mejia, we emphasized that the defendant,

after having been given the Miranda warnings three times and having

signed a form that indicated that he understood those rights,

"began responding to questions willingly and even offered to become

an informant."

. We explained that this sequence of

events indicated that "this was a voluntary conversation that Mejia

undertook after having been fully advised of his rights."

- 18 - C.

Although we have concluded that Donald did not waive his

Miranda rights as early as the government belatedly asserted at

oral argument that he had, there is still the question as to

whether Officer Morris responded "No." In asserting that any

claimed waiver that was made was not a valid one, Donald contends

that Officer Morris did make that response and thus that there was

no valid waiver. The District Court found, however, that Officer

Morris did not so respond or, at least, that the answer Officer

Morris gave was "unintelligible."

Our review of this factual finding by the District Court

is for clear error, which means we must "defer to the [D]istrict

[C]ourt's finding[] unless 'the record, read as a whole, gives

rise to a strong, unyielding belief that a mistake has been made.'"

United States v. Negron-Sostre,

(1st Cir. 2015)

(quoting United States v. Hughes,

(1st Cir.

2011)). As the District Court pointed out, the moment in question

features Officer Morris, Donald, and Agent DiTullio all speaking

and interrupting each other in quick succession, sometimes

speaking simultaneously. Indeed, at just the moment that Officer

Morris -- on Donald's account -- says "No," Agent DiTullio is also

speaking. And, whether due to microphone volume levels or the

volumes of their actual voices, both Agent DiTullio's and Donald's

- 19 - voices appear to be louder in the recording than Officer Morris's

voice, particularly in instances when multiple people are speaking

simultaneously. So, this was not a situation in which the District

Court was confronted with just a simple exchange between two

parties to decipher.

Nonetheless, our review of the recording still leads us

to conclude that it is clear that Officer Morris did say "No" at

just the moment that Donald argues that he did. Moreover, there

was no finding by the District Court, insofar as Officer Morris

did intelligibly respond "No," that Donald did not hear the

statement. For these reasons, we conclude that Donald has

satisfied his burden under the clear-error standard in contending

that Officer Morris responded "No" in an intelligible manner when

Donald asked, "None of this can be used against me, can it?" Cf.

Scott v. Harris,

, 378–81 (2007) (granting summary

judgment for petitioner on the ground that "[r]espondent's version

of events is so utterly discredited by the [videotape recording of

the car chase at issue] that no reasonable jury could have believed

him" and commenting that the "Court of Appeals should not have

relied on such visible fiction; it should have viewed the facts in

the light depicted by the videotape"); see also United States v.

Reinberg,

(6th Cir. 2023) (concluding that the

district court's finding "wasn't clearly erroneous" based on a

- 20 - review of the video because "[a]t best, the video is partially

ambiguous" and "the district court's interpretation of the video

was the most plausible").

D.

Having shown that no waiver occurred before Officer

Morris said "No" and that it was clear error for the District Court

to find that Morris did not make that response, Donald still must

show one thing more to succeed on his challenge to the denial of

his suppression motion. He must show that the government cannot

meet its burden to show that his purported waiver following that

"No" response was made "voluntarily, knowingly and intelligently."

Moran,

(quoting Miranda,

).

To show that a Miranda waiver was voluntary, the

government must show that it "was the product of a free and

deliberate choice rather than intimidation, coercion, or

deception."

To show that the waiver was knowing, the

government must show that it was made "with a full awareness of

both the nature of the right being abandoned and the consequences

of the decision to abandon it," meaning that the government must

show that the defendant not only "knew he could stand mute and

request a lawyer" but also "that he was aware of the [government's]

intention to use his statements to secure a conviction[.]"

at

421–22 (emphasis added).

- 21 - Donald contends that the government cannot meet its

burden to show that his waiver was knowing in light of the "No"

response because of the confusion that response could have created

about the effect under Miranda of his speaking to law enforcement

about what was found at the property where the searches were

executed. He contends that Hart v. Att'y Gen. of Fla.,

(11th Cir. 2003), supports his contention.

There, the Eleventh Circuit looked to statements made by

investigators even after the defendant had already signed an

explicit Miranda waiver -- such as that "honesty wouldn't hurt

him," as well as that a "con" of his getting counsel was that

counsel might advise him not to respond to some of the officers'

questions -- and concluded that because those statements

contradicted the earlier Miranda warnings, they rendered the

defendant's waiver "not voluntary, knowing, and intelligent."

at 894–95. In the same way, Donald contends, he could have

reasonably interpreted Officer Morris's "No" response as an

assurance that none of his statements could be used against him

and thus as a statement that contradicted the earlier Miranda

warnings in a way that rendered any subsequent waiver of Donald's

Miranda rights invalid.

The government responds that the "No" response, even if

made, is not determinative. That is so in part, the government

- 22 - contends, because of the nature of the question that Donald asked

before that response was given.

According to the government, the District Court

"implicitly found that [Donald's question] was referring to some

kind of separate promise relating to his cooperation, not his

Miranda rights" (emphasis added). The government thus reasons

that there is no basis for concluding that the "No" response, even

if made, could have caused any confusion on Donald's part about

what Miranda itself provided, given that the District Court found

that response would have at most concerned the nature of a separate

cooperation agreement that Donald may have thought he had. We are

not persuaded.

For starters, we note that even if the District Court

found, and did not clearly err in so finding, that Donald's

question was referring to a separate cooperation agreement, we

must still decide whether, in consequence of the "No" response,

the government has met its burden to establish that Donald

knowingly, intelligently, and voluntarily waived his Miranda

rights. But insofar as the government means to argue that the

District Court made a finding of fact that the question did not

reflect any confusion on Donald's part about what the effect under

Miranda would be of his entering into a conversation with law

enforcement about what was found at the property, such that our

- 23 - review of the District Court's assessment of whether he was

confused in that respect is only for clear error, we reject the

contention.

The assessment of what Donald ultimately understood

about Miranda -- as well as what he understood would be the

consequences of waiving its protection -- presents a question of

law, not fact. And that is because the question concerns whether,

based on the totality of the circumstances, the government has

shown that Donald did knowingly waive his Miranda rights by

speaking to law enforcement as he did following the "No" response.

See Rojas-Tapia,

. As a result, we review that

question de novo and not for clear error.

Indeed, we do not understand the District Court itself

to have been operating on a different understanding in ruling as

it did. Even if the District Court found the question that Donald

asked pertained to a cooperation agreement, the District Court

explicitly referred to the remainder of its assessment of whether

the waiver was knowing, intelligent, and voluntary, and its

resulting conclusions, as being "[b]ased" on a "totality of the

circumstances."

That said, the government does also argue that, even on

de novo review, the waiver was valid, given the totality of the

circumstances. And so we must address that contention as well.

- 24 - In making this argument, the government rightly points

to aspects of the record that show that this case is somewhat

distinct from Hart,

. After all, unlike in that case,

there seems to be no dispute that Donald had a basic understanding

of Miranda. As the government argues, Donald testified at the

reconsideration hearing that "there's no disagreement that [he]

generally understood what [his] rights were" or that he believed

that "in certain context[s] . . . an individual can provide

statements without the worry of having those statements come back

to haunt them, such as . . . in a proffer session." Building off

those features of the record, the government further contends that,

as a result, even if Officer Morris did say "No," that response

would not merit vacating Donald's convictions because a de novo

review of the totality of the circumstances reveals that the

response did not actually cause Donald to become confused about

the existence of his right to remain silent under Miranda. Thus,

the government argues, Donald's contention that there was no valid

Miranda waiver fails and that he, at most, would have had a non-

Miranda-based due-process claim -- which he has not brought --

that his confession was obtained through "coercive official

tactics," see Bezanson-Perkins,

.

But, based on our de novo review of the record, we cannot

conclude that the government has shown that Donald's familiarity

- 25 - with the criminal-justice system was sufficiently nuanced that it

would educate him about whether, under Miranda, statements he made

while cooperating in this matter were immunized, even though the

record does show that he generally understood that statements that

he made would not be immunized. Thus, consistent with Hart, we

conclude from a de novo review of the record that the government

has failed to show that, given the totality of the circumstances,

the "No" response did not cause Donald to misunderstand the

protection that he was foregoing under Miranda by speaking as he

did when he did.

To that point, Donald stated -- after he received the

"No" response but before he spoke in hypotheticals -- that he did

not want to "put [him]self under the . . . gun giving statements"

that would "get[] held against [him] in the court of law as

evidence." True, that statement could show, as the government

contends, that Donald was not under the impression that, under

Miranda, he could speak with impunity. But, it equally could show

that Donald was simply confused about how freely he could speak in

this setting under Miranda without giving up its protections, given

the "No" response he had received. Indeed, even the District Court

observed at trial based on this statement by Donald that "[i]t's

almost as if [Donald] thought . . . that he could say whatever he

wanted with impunity because he had invoked his [rights] before."

- 26 - Thus, while we appreciate the District Court's evident

care in considering this fact-dependent Miranda issue, we cannot

conclude -- given the equivocal nature of the record on the key

point -- that the government has satisfied its burden to show that

Donald validly waived his Miranda rights. And, as this error was

not harmless, we agree with Donald that none of his convictions

can stand.

III.

For the reasons stated above, the convictions are

vacated, and the case is remanded for further proceedings

consistent with this opinion.

- 27 -