United States v. Joseph Samir Zakhari

RECOMMENDED FOR PUBLICATION

Pursuant to Sixth Circuit I.O.P. 32.1(b)

File Name: 23a0231p.06

UNITED STATES COURT OF APPEALS

FOR THE SIXTH CIRCUIT

┐

UNITED STATES OF AMERICA,

│

Plaintiff-Appellee, │

> No. 22-5328

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v. │

│

JOSEPH SAMIR ZAKHARI, │

Defendant-Appellant. │

┘

Appeal from the United States District Court for the Western District of Kentucky at Louisville.

No. 3:19-cr-00208—Rebecca Grady Jennings, District Judge.

Argued: April 27, 2023

Decided and Filed: October 23, 2023

Before: KETHLEDGE, WHITE, and STRANCH, Circuit Judges.

_________________

COUNSEL

ARGUED: Michael R. Mazzoli, COX & MAZZOLI PLLCE, Louisville, Kentucky, for

Appellant. Terry M. Cushing, UNITED STATES ATTORNEY’S OFFICE, Louisville,

Kentucky, for Appellee. ON BRIEF: Michael R. Mazzoli, COX & MAZZOLI PLLCE,

Louisville, Kentucky, for Appellant. Terry M. Cushing, UNITED STATES ATTORNEY’S

OFFICE, Louisville, Kentucky, for Appellee.

WHITE, J., delivered the opinion of the court in which STRANCH, J., joined in full and

KETHLEDGE J., joined in Section III only. KETHLEDGE, J. (pp. 21–23), delivered a separate

opinion concurring in part and dissenting in part.

No. 22-5328 United States v. Zakhari Page 2

_________________

OPINION

_________________

WHITE, Circuit Judge. Defendant-Appellant Joseph Zakhari was convicted of

attempting to persuade a minor to engage in illegal sexual activity, in violation of 18 U.S.C.

§ 2422(b) (Count 1); attempting to transmit an obscene image to a minor, in violation of

18 U.S.C. § 1470 (Count 2); and attempting to produce child pornography, in violation of

18 U.S.C. § 2251(a) and (e) (Count 3). The district court sentenced him to the applicable

mandatory minimum term of fifteen years in prison. On appeal, Zakhari argues that the court

erroneously denied his motion to suppress his statement to police as obtained in violation of his

right to counsel and his motion to dismiss Count 3 as vindictive. Because the suppression

motion should have been granted and the district court did not sufficiently consider the claim of

prosecutorial vindictiveness, we REVERSE the denial of the motion to suppress, VACATE the

conviction, and REMAND for a new trial and reconsideration of the motion to dismiss.

I.

A.

In May 2019, Zakhari was in the fifth year of an MD-PhD program at the University of

Louisville and planned to become a cardiothoracic surgeon. His family was in Maryland, and his

school friends had started residencies around the country, so he was lonely. That month, while

investigating human trafficking at the Kentucky Derby, a detective with the Kentucky Attorney

General’s Office created a fake dating profile for “Dani” on the website MeetMe. The profile,

which used an image of a female officer when she was in her late teens or early twenties, showed

“Dani” was a single, eighteen-year-old female in Louisville looking for “Friendship, Dating,

Chat” and that she had an account under the name “boredcrbgirl” on the messaging application

Kik. Five days after the profile was posted, Zakhari wrote “Hey” to “boredcrbgirl” on Kik but

received no response. He then spent the summer in Maryland and returned to Louisville in the

fall.

No. 22-5328 United States v. Zakhari Page 3

In October, Zakhari began a spree of messages to sixty-one social-media accounts over

three days on MeetMe, Kik, and Badoo (another online platform), including “boredcrbgirl,” who

was one of the few to respond. He wrote, “Hey. How are you?”; “Bored,” she replied. R. 193,

PID 1839. Zakhari replied, “Same. And horny,” to which “boredcrbgirl” wrote, “LOL. How

old are you?” At this point, the following exchange occurred:

Zakhari: 32. How old are you?

“boredcrbgirl”: NVM. 15.

Zakhari: Oh. I thought you were older.

“boredcrbgirl”: Yeah.

Zakhari: So you don’t want to jerk off together?

“boredcrbgirl”: Um, like FR?

Zakhari: Yeah. Are you horny?

“boredcrbgirl”: WDY think.

Zakhari: Yes.

“boredcrbgirl”: LOL. My mom is gonna be here at 12:00.

R. 193, PID 1839-40.

Zakhari continued chatting with “boredcrbgirl” over the next two days, making lewd

suggestions, requesting photographs, and sending pictures of his penis. Among other things, he

wrote: “Have toys?”; “You want to fuck in person?”; “Let me see more pics of you first”; “And

you fuck older guys?”; “Send me some naughty pics of you”; “Can I see you in underwear?”;

“Could you handle my big dick?”; “Do you like giving head?”; “I also want to fuck your ass”;

and “Is your pussy shaved? . . . Can I see?” Id. at PID 1841, 1843-46, 1849, 1851.

“boredcrbgirl” replied, “WDY think?” when he asked about having sex in person, and “Yeah,”

when he asked about sex with older men, but she never made sexual suggestions of her own. Id.

at PID 1843. In response to picture requests, “boredcrbgirl” sometimes sent images of the

female officer as an adult but never indulged Zakhari’s requests for sexual images.

At times, Zakhari expressed doubt about how old “boredcrbgirl” truly was and whether

she was real. “Are you a real person?,” he wrote, and he asked for “a pic of you doing the peace

sign”; he received an image of the officer posing less than a minute later. R. 193, PID 1848.

No. 22-5328 United States v. Zakhari Page 4

He expressed confusion about why “boredcrbgirl” was home from school for two days in a row,

and he found the shift that “boredcrbgirl” said her mom worked as a nurse odd based on his

knowledge of hospitals. When he gave his address, “boredcrbgirl” remarked it was near “Z

Bar,” and he then asked twice for her age again before “boredcrbgirl” responded, “Told you.

15.” Id. PID 1854-55. “Are you sure you aren’t 18?,” he asked; “Nah, I’m sure. LOL,” she

replied. Id. at PID 1855.

Zakhari pushed for “boredcrbgirl” to come to his apartment for sex, but she said she

wanted to meet at her place. “Hm. You are underage,” he wrote, “I’m just nervous about

coming to your place . . . [a]nd fucking a 15 year old.” Id. at PID 1855, 1857. “If you came over

to my place your mom couldn’t walk in on us,” he explained. Id. at PID 1857. Eventually, he

suggested she “take an Uber over to my place and ride my hard cock,” and she asked, “How long

is it to get there?” Id. PID 1862-63. They agreed on a plan for Zakhari to send an Uber.

The officer who had posed for the images arrived at Zakhari’s residence in the Uber

while agents were positioned nearby. “I’m outside,” she messaged; “Coming down,” he

responded. Id. at PID 1865. When he met her, he said, “Hey, how are you?,” and asked if she

was “ready to go upstairs.” Id. at PID 1905. He was then arrested and brought up to his

apartment where officers conducted a search before transporting him to the Crimes Against

Children Unit.

The detective who had been messaging with Zakhari interrogated him at the unit,

beginning with noting the importance of the questioning and giving the Miranda warnings.1 “Do

you understand what I just told you?,” the detective asked; Zakhari replied, “Yes sir,” and the

detective followed up with, “Do you want to talk to me right now?” R. 203, PID 2323. Zakhari

put his head in his hands and paused for ten seconds: “I don’t know who to call, I don’t know if

I call my dad or my sister. Oh my god.” R. 60, PID 428, Ex. 1 05:43-06:00. He dropped his

1

Zakhari was told: “I have to advise you of your rights because[,] like I said[,] you’re in custody

obviously, alright, and I know you know that you have those rights[,] so I’m gonna read ‘em to you. . . . You have

the right to remain silent[;] anything you say can and will be used against you in court. You have the right to have

[an] attorney present during questioning[;] if you cannot afford an attorney but desire one the court will appoint one

for you at no cost. You can stop the questioning at any time by refusing to answer further or by requesting to

consult your attorney.” R. 203, PID 2323 (emphasis added).

No. 22-5328 United States v. Zakhari Page 5

head again, was silent for another long pause, and said, “I can answer some questions and then

maybe call, I don’t even know what to think any more, I—I—.” Id. at 06:05-06:13. The

detective interjected, “Yeah, I understand, listen. It’s been a big day, right?,” and assured

Zakhari that he would “help [him] get through this.” R. 203, PID 2324.

After Zakhari responded to some basic questions about his name and birth date, the

following exchanged occurred:

Detective: And how about your social security number?

Zakhari: Can I call my dad?

Detective: Well, you know, I don’t have your phone and I can’t give it

to you right now.

Zakhari: But you said I can stop at any time and call if I wanted to.

Detective: Yeah, well, is your dad an attorney?

Zakhari: My sister’s an attorney.

Detective: Do you wanna call your sister?

Zakhari: Yeah, I mean sh—2

Detective: If you want to, yes but that’s gonna be the end of us

talking.

Zakhari: Well—

Detective: And that’s not my rule, that’s just the way it is.

Zakhari: I understand I just don’t know what more you want me to

say. I made a huge mistake if you want me to say that.

R. 60, PID 428, Ex. 1 07:09-07:45. After this, Zakhari continued to answer the detective’s

questions and made a series of incriminating statements. He admitted he “decided to

communicate with somebody I shouldn’t have been communicating with” and admitted he

should not have been communicating with the person because she was “a minor” and he was not

“under the age of 18.” R. 203, PID 2330. “That’s illegal,” he said; the detective responded, “So

I mean like I said obviously you’re not a lawyer but I mean you, you have knowledge of the

law,” and Zakhari said, “Yes sir.” Id. A few minutes later, Zakhari said, “Sir, I would like my

2

There is a pause of approximately four seconds between Zakhari saying, “Yeah, I mean sh—,” and the

detective interjecting. R. 60, PID 428, Ex. 1 07:26-07:30.

No. 22-5328 United States v. Zakhari Page 6

lawyer at this point.” Id. at PID 2340. The detective spoke with Zakhari for a few more minutes

before allowing him to speak with his father.

B.

In November 2019, Zakhari was indicted on two charges: attempting to persuade a minor

to engage in illegal sexual activity, in violation of 18 U.S.C. § 2422(b), and attempting to

transmit an obscene image to a minor, in violation of 18 U.S.C. § 1470. In June 2020, the

government added a third charge—attempting to produce child pornography in violation of

18 U.S.C. § 2251(a) and (e)—which increased the mandatory minimum punishment from ten to

fifteen years.

Zakhari moved before trial to suppress his statements, arguing he had invoked his right to

an attorney. The district court found that Zakhari’s later statement—“I would like my lawyer at

this point”—was a clear invocation of his rights and excluded the remainder of the interrogation.

R. 75, PID 710. But the court found that Zakhari had not made “a clear and unambiguous

invocation of his right to counsel” earlier when he identified his sister as an attorney and said he

wanted to call her. Id. at PID 708-10. Thus, the jury was permitted to watch footage of his

confession.

Additionally, Zakhari sought to strike the third charge, arguing it was the product of

prosecutorial vindictiveness. The district court denied that motion, accepting the government’s

explanations and finding that the volume and nature of the motions practice to that point showed

no reasonable likelihood of vindictiveness.

The jury convicted Zakhari of all charges. At sentencing, the district court noted that

Count 3 yielded a “more significant mandatory minimum of 15 years that was not there before”

and thus the court was “quite frankly limited in what [it could] do . . . based on the charging

decisions.” R. 198, PID 2297. The court explained that it had not struck Count 3 because the

“standard for that is just incredibly high and so difficult to prove” but acknowledged “there were

points made in that which now that I’ve sat through trial, I kind of understand.” Id. Specifically,

the court said that the interactions were in a single course of conduct and Zakhari’s exchange

was “probably the same interaction that would have happened if [‘boredcrbgirl’] were 16 or 19

No. 22-5328 United States v. Zakhari Page 7

or 50” because an exchange of pictures based on trying to learn “who this other person is on the

end of the line” while planning a sexual encounter is “all part and parcel . . . of one criminal

scheme.” Id. at PID 2298. For this reason, the court concluded that Count 3 could “have been

added at the very beginning of the case” and that “if it was going to be added, it was there all

along.” Id.

Additionally, the court observed that there were “facts that came to light during the trial

that definitely caused [the court] some pause.” Id. at PID 2299. Specifically, the court said:

I think it’s very reasonable to assume . . . that Mr. Zakhari was looking at a

website that he believed showed this individual as 18. He asked questions when

he got in this next chat and maybe didn’t believe the statement . . . that she was

. . . 15 right from the start and [he] continued to inquire and ask questions. . . .

[N]one of that really made a big difference to the jury based on what the jury

instructions were . . . because at the end of the day she was 15, he ordered the

Uber, he took that step and went forward.

Id. The court found that Zakhari “had an irrational and inappropriate reaction” and everything

changed for him from “that one moment which lasted . . . less than an hour.” Id. at PID 2300.

“[He was] not an individual who was seeking out minors,” the court said, and “seem[ed] to have

almost stumbled into [contact] by not believing the one website connected to the other website.”

Id. PID 2300-01. Accordingly, it found the fifteen-year mandatory minimum “in excess of what

would be necessary,” expressing regret to be “hand-tied” by Count 3. Id. at PID 2304.

II.

Zakhari argues that the district court erred in denying his motion to suppress the entire

interrogation because he invoked his right to counsel when he said he wanted to call his sister,

whom he had identified as an attorney. We review a district court’s factual findings for clear

error and legal rulings de novo, including a ruling on whether a defendant invoked his rights

under the Fifth Amendment. United States v. Potter, 927 F.3d 446, 450 (6th Cir. 2019).

A.

Once a person communicates “his desire to deal with the police only through counsel,” he

is “not subject to further interrogation by the authorities until counsel has been made available to

No. 22-5328 United States v. Zakhari Page 8

him.” Edwards v. Arizona, 451 U.S. 477, 484-85 (1981). “[A]ll questioning must cease.” Smith

v. Illinois, 469 U.S. 91, 98 (1984). This “bright-line prohibition” prevents investigators from

“wear[ing] down the accused” in “explicit or subtle, deliberate or unintentional” ways so as to

convince him “to incriminate himself notwithstanding his earlier request for counsel’s

assistance.” Id. The burden is on the government to show a proper waiver of the right to

counsel. See Seymour v. Walker, 224 F.3d 542, 554 (6th Cir. 2000).

To invoke the right to counsel, the accused must make a “statement that can reasonably

be construed to be an expression of a desire for the assistance of an attorney.” Davis v. United

States, 512 U.S. 452, 459 (1994) (quoting McNeil v. Wisconsin, 501 U.S. 171, 178 (1991)). “If

an accused makes a statement concerning the right to counsel ‘that is ambiguous or equivocal’ or

makes no statement, the police are not required to end the interrogation, or ask questions to

clarify whether the accused wants to invoke his or her Miranda rights.” Berghuis v. Thompkins,

560 U.S. 370, 381 (2010) (citation omitted).

Any ambiguity must come from the statement itself or what led to it. It is “intolerable” to

“[u]s[e] an accused’s subsequent responses to cast doubt on the adequacy of the initial request.”

Smith, 469 U.S. at 98-99. “No authority, and no logic, permits the interrogator to proceed . . . on

his own terms and as if the defendant had requested nothing, in the hope that the defendant might

be induced to say something casting retrospective doubt on his initial statement that he wished to

speak through an attorney or not at all.” Id. at 99 (alteration in original) (quoting People v.

Smith, 466 N.E.2d 236, 241 (Ill. 1984) (Simon, J., dissenting)).

B.

The district court found Zakhari’s request to call his sister equivocal because, when asked

if he wished to call her, he “quickly stammered through the beginning of an affirmative answer”

but then expressed “a different thought” by saying “yea—” and then “I mean she” before falling

silent. R. 75, PID 710. The court reasoned that this “more closely resemble[d] an attempt to

speak with family than a serious request for counsel.” Id. (alteration in original) (citation

omitted). We disagree.

No. 22-5328 United States v. Zakhari Page 9

The following facts are informative. Less than two minutes after hearing his rights, after

answering only two short questions, Zakhari asked to call his father, and, when the detective

deflected the request by referring to Zakhari’s phone, Zakhari stated that he thought he could

stop and make a call at any point. This was a clear reference to the detective’s prior statement:

“You can stop the questioning at any time by refusing to answer further or by requesting to

consult your attorney.” R. 203, PID 2323. And when the detective responded, “Yeah, well, is

your dad an attorney?,” Zakhari immediately responded: “My sister’s an attorney.” Id. at PID

2325. He did not say something like, “No, but I’d like to talk to him anyway”; his immediate

response was to identify a lawyer he knew. When the detective asked, “Do you wanna call your

sister?,” Zakhari responded after less than a second: “Yeah, I mean sh—.”3 R. 60, PID 428, Ex.

1 07:22-07:27.

With these facts in mind, we disagree with the district court’s conclusion that Zakhari’s

request to call his father was “an attempt to speak with family.” It is true that a valid request

must be for “the particular sort of lawyerly assistance that is the subject of Miranda,” which

concerns the defendant’s “desire to deal with the police only through counsel.” United States v.

Suarez, 263 F.3d 468, 486 (6th Cir. 2001) (first quoting McNeil, 501 U.S. at 179; then quoting

Edwards, 451 U.S. at 484). But we have never suggested that a request is less valid where

counsel is family. Such a rule would be illogical: It is common sense for a person to seek

“lawyerly assistance” from the lawyer they know best and likely the only lawyer whose contact

information they know offhand.

Moreover, the factual context shows Zakhari had “lawyerly assistance” in mind. See

Abela v. Martin, 380 F.3d 915, 926 (6th Cir. 2004) (analyzing “the circumstances surrounding

the statement”), abrogated on other grounds by Guilmette v. Howes, 970 F.3d 698 (6th Cir.

2010) (en banc). By referring to the detective’s prior statement that the interrogation could stop

at any time, Zakhari specifically indicated he wanted to “stop.” Cf. Potter, 927 F.3d at 451

(finding no invocation where defendant “never once said that he wanted to stop”). He asked to

call his dad almost immediately after being told he could call an attorney, not a family member;

3

Although the district court found that Zakhari said the word “she,” our review shows that he only uttered

the syllable “sh.” R. 60, PID 428, Ex. 1 07:22-07:27. Further, he clearly said the full word “yeah,” not “yea—.” Id.

No. 22-5328 United States v. Zakhari Page 10

instantly identified his sister as an attorney when asked if dad was one; and said “Yeah” without

hesitation after being asked directly whether he wanted to call her. Further, the detective

understood that Zakhari sought “lawyerly assistance” because he told Zakhari that questioning

would cease if he called his sister. Cf. Abela, 380 F.3d at 926 (finding persuasive that officer’s

actions showed understanding of request for counsel). Zakhari plainly sought counsel within the

meaning of Miranda, regardless of his relation to the attorney he wished to contact.

Nor was Zakhari’s invocation otherwise ambiguous or equivocal. True, he said, “I mean

sh—” after saying “Yeah,” that he did want to call his sister, and he paused for four seconds

before the detective interrupted. But he did not stammer in saying “Yeah,” as the district court

found. Nor did he introduce “a different thought”; he had four seconds to contradict the

affirmative response given but did not do so. Rather, “I mean sh—” emphasized the import of

his earlier communication: that he wanted to stop and make a call. It is common when speaking

for people to stop midsentence while still expressing a clear idea, and “a suspect need not ‘speak

with the discrimination of an Oxford don.’” Davis, 512 U.S. at 452 (quoting id. at 476 (Souter,

J., concurring)). Nor must the accused appear unshakeable in his decision or enthusiastic about

calling counsel. See Smith, 469 U.S. at 97 (finding invocation based on “Uh, yeah. I’d like to do

that”); Yenawine v. Motley, 402 F. App’x 997, 998 (6th Cir. 2010) (per curiam) (“I might need to

speak with my lawyer about whether I should talk with you.”); Kyger v. Carlton, 146 F.3d 374,

376 (6th Cir. 1998) (“I’d just as soon have an attorney.”); United States v. Wysinger, 683 F.3d

784, 790-91 (7th Cir. 2012) (“I mean, but can I call one now? That’s what I’m saying.”); Wood

v. Ercole, 644 F.3d 83, 91 (2d Cir. 2011) (“I think I should get a lawyer.”); Cannady v. Dugger,

931 F.2d 752, 755 (11th Cir. 1991) (“I think I should call my lawyer.”).

As made plain in Abela, an invocation is sufficient despite a verbal hedge when other

elements of the situation establish that the defendant sought to invoke his rights. Abela said,

“maybe I should talk to an attorney by the name of William Evans,” 380 F.3d at 926, which is

more equivocal than Zakhari’s affirmative answer to the direct question whether he would like to

call his sister. This court found Abela’s statement clear and unequivocal because the

“surrounding circumstances” showed he identified a specific attorney, and the interrogator

construed the statement as an invocation. Id. Those same circumstances are present here.

No. 22-5328 United States v. Zakhari Page 11

Zakhari had just identified his sister as an attorney. And the detective did not need to clarify by

inquiring, “Are you seeking her legal advice?” He understood what Zakhari sought and told him

questioning would stop.

For good reason, we are unaware of a case finding no invocation where a defendant

replied affirmatively to a direct question about whether he wanted to call an attorney. We are

mindful that the Supreme Court explained in Davis that the Edwards rule is meant to provide “a

bright line that can be applied by officers in the real world of investigation and interrogation

without unduly hampering the gathering of information.” 512 U.S. at 461. In that spirit, the

Court explained, “this clarity and ease of application would be lost” with a standard that

“require[d] questioning to cease if a suspect makes a statement that might be a request for an

attorney.” Id. Under that alternative regime, “officers would be forced to make difficult

judgment calls about whether the suspect in fact wants a lawyer even though he has not said so,

with the threat of suppression if they guess wrong.” Id.

In this case, Zakhari had already made statements that could possibly have sought to

invoke his right to counsel (i.e., “Can I call my dad?” and “[Y]ou said I could stop at any time.”)

and the detective sought clarity. The detective then asked Zakhari directly if he wanted to call

someone Zakhari had identified as an attorney, and Zakhari said, “Yeah, I mean sh—,” before

the detective re-engaged with him. Although ineloquent, this was an affirmative response. If we

required more in this situation, we would essentially invite officers to ask, “But are you really

sure?” before the right to counsel is invoked. Such a standard would drain Miranda of meaning

and undermine the ease of Edwards. Officers must take defendants at their word if they answer

that they would like to speak to an attorney—as the officer did here, R. 203, PID 2325 (“If you

want to, yes[,] but that’s gonna be the end of us talking”)—and cease questioning.

Accordingly, we conclude that Zakhari adequately invoked his Fifth Amendment right to

counsel and the district court should have granted his motion to suppress the entirety of his

interrogation.

No. 22-5328 United States v. Zakhari Page 12

C.

We turn to the government’s alternative argument that, even if the district court erred in

denying the motion to suppress, this error was harmless because of other evidence in the record:

the Kik messages, in which “boredcrbgirl” repeatedly stated she was 15; the fact that Zakhari

ordered an Uber; and Zakhari’s utterances immediately after arrest (“I can’t believe how stupid I

was” and “What [was] I . . . thinking?”). R. 194, PID 1971.

The admission of the interrogation was not harmless. A constitutional error is harmless if

it “appears ‘beyond a reasonable doubt that the error complained of did not contribute to the

verdict obtained.’” Neder v. United States, 527 U.S. 1, 15 (1999) (quoting Chapman v.

California, 386 U.S. 18, 24 (1967)). As the Supreme Court has cautioned: “A confession is like

no other evidence. Indeed, ‘the defendant’s own confession is probably the most probative and

damaging evidence that can be admitted against him.’” Arizona v. Fulminante, 499 U.S. 279,

296 (1991) (citation omitted). Given the power of a confession, our review of the evidence, and

the district court’s observation at sentencing that Zakhari had a plausible defense that he did not

actually believe “boredcrbgirl” was underage, the government has not shown beyond a

“reasonable doubt” that the confession video did not contribute to Zakhari’s conviction. We thus

reverse the district court’s denial of the motion to suppress, vacate the conviction, and remand

for a new trial.

III.

Next, Zakhari argues that the district court abused its discretion when it denied his

motion to dismiss Count 3, the child-pornography count, rejecting his claim of prosecutorial

vindictiveness. This charge, which increased the mandatory minimum by five years, was added

on June 17, 2020, seven months after the original indictment was handed down on November 20,

2019.

A.

We review for abuse of discretion a district court’s decision whether to dismiss an

indictment for prosecutorial vindictiveness. United States v. LaDeau, 734 F.3d 561, 565 (6th

No. 22-5328 United States v. Zakhari Page 13

Cir. 2013). “A district court abuses its discretion ‘when it relies on erroneous findings of fact,

applies the wrong legal standard, misapplies the correct legal standard when reaching a

conclusion, or makes a clear error of judgment.’” Id. at 565-66 (quoting Schlaud v. Snyder, 717

F.3d 451, 457 (6th Cir. 2013)). “Because a district court has no discretion not to abide by

governing law, an erroneous legal conclusion deserves no deference on appeal.” Id. at 566.

Thus, “a district court commits error requiring reversal if its determination whether to dismiss an

indictment for prosecutorial vindictiveness depends upon a misapplication of pertinent law,” but

“where the district court’s dismissal determination hinges upon factual findings, we defer to the

district court’s decision unless the findings upon which it was predicated are clearly erroneous.”

Id.

The Fifth Amendment forbids the government from punishing defendants for exercising

their constitutional and statutory rights. See United States v. Goodwin, 457 U.S. 386, 372

(1982). Consequently, defendants may challenge the government’s charging decisions for actual

or presumptive vindictiveness. See LaDeau, 734 F.3d at 566. The latter theory recognizes a

rebuttable presumption of vindictiveness if the defendant shows a “realistic likelihood” that a

charge was vindictive. Goodwin, 457 U.S. at 384 (quoting Blackledge v. Perry, 417 U.S. 21, 27

(1974)). This standard is objective and considers “whether a reasonable person would think

there existed a realistic likelihood of vindictiveness,” not the “defendant’s subjective

impressions.” United States v. Andrews, 633 F.2d 449, 454 (6th Cir. 1980) (en banc).

To assess this likelihood, a court “must weigh two factors: (1) the prosecutor’s ‘stake’ in

preventing assertion of the protected right and (2) the reasonableness of the prosecutor’s

actions.” United States v. Poole, 407 F.3d 767, 776 (6th Cir. 2005) (quoting Andrews, 633 F.2d

at 454). Once a reasonable likelihood is found, a presumption arises in defendant’s favor and the

government must rebut it “with ‘objective, on-the-record explanations’ such as ‘governmental

discovery of previously unknown evidence’ or ‘previous legal impossibility.’” LaDeau, 734

F.3d at 566 (quoting Bragan v. Poindexter, 249 F.3d 476, 482 (6th Cir. 2001)). This approach

“reconcile[s] two conflicting rules of law: 1) prosecutors have and need broad discretion to file

charges where there is probable cause that someone has broken the law; 2) vindictive conduct by

No. 22-5328 United States v. Zakhari Page 14

persons with the awesome power of prosecutors . . . is unacceptable and requires control.”

Andrews, 633 F.2d at 453.

In LaDeau, we affirmed the district court’s decision to presume vindictiveness where the

defendant won a motion to suppress that “eviscerated” the government’s case and then, five days

before trial, the government obtained a superseding indictment that changed the prescribed

sentencing range from 0-10 years’ imprisonment to 5-20 years’ imprisonment, and that was also

based on a new theory of guilt applied to the same conduct as before. 734 F.3d at 564-63, 569.

There was “little reason to suspect that the prosecutor’s view of LaDeau’s case changed

significantly between the two indictments,” which occurred thirteen months apart, “given that the

government already possessed all of the relevant evidence that supported the superseding

indictment well before procuring the first indictment.” Id. at 565, 568.

B.

The parties submitted briefs to the district court on Zakhari’s vindictiveness claim and

echo their arguments on appeal. Zakhari argued that the addition of a new count substantially

increasing his mandatory minimum, without new evidence and after vigorous motions practice,

established a presumption of vindictiveness. Specifically, he noted that, before the superseding

indictment (in June 2020), he moved to amend his conditions of release on several occasions (in

December 2019, February 2020, and April 2020); moved for return of electronic devices (in

January 2020); moved to suppress his interrogation (in February 2020); sought discovery of

evidence connecting the “Dani” account on MeetMe to the “boredcrbgirl” Kik account (in May

2020); and moved to compel the appearance of the decoy officer—whose identity the

government had not revealed—at the suppression hearing (in June 2020). The government

opposed all these motions except for Zakhari’s first motion to modify his terms of release.

Lastly, Zakhari noted that, at the sentencing hearing for a 2007 child-pornography case involving

a different defendant, a district court cautioned the same prosecutor against arguing that the

defendant should be penalized for using a motion to suppress to assert his constitutional rights.

The government responded by explaining its decision. According to its brief, in January

2020, the prosecutor was on the faculty of a course that discussed charging and sentencing in

No. 22-5328 United States v. Zakhari Page 15

child-exploitation cases, and around this time also worked on a case similar to Zakhari’s, in that

there was an alleged attempt at exploitation and the defendant had requested images. That case

involved debate over applying U.S. Sentencing Guideline § 2G1.3(c)(1), which assigns a base

offense level of 32 “[i]f the offense involved causing, transporting, permitting, or offering or

seeking by notice or advertisement, a minor to engage in sexually explicit conduct for the

purpose of producing a visual depiction of such conduct.” Additionally, in February 2020, the

prosecutor reviewed cases from recent sting operations with detectives and resolved to present

five indictments to the March grand jury, including Zakhari’s superseding indictment. She

decided, for “consistency,” that “if the defendant asked the undercover for sexually explicit

images, an attempted production of child pornography was included rather than relying on the

cross reference in U.S.S.G. § 2G1.3(c)(1) to address the conduct.” R. 71, PID 552. Because of

COVID-19, the grand jury did not convene again until June 17, 2020, when it handed down

Zakhari’s superseding indictment. The government also provided context for the 2007 case

Zakhari pointed to and emphasized that this occurred over a decade before.

The district court found that Zakhari failed to show enough to presume vindictiveness.

The court reasoned that Zakhari’s pretrial motions were “routine and minimally burdensome

filings” and thus “unlikely to prompt a vindictive prosecutorial response,” which the court found

contrasted with LaDeau, where the defendant’s successful motion to suppress forced the

government to start over, and the government made a new charging decision right before trial.

R. 109, PID 850-51 (quoting 734 F.3d at 568). The court further noted that the government’s

brief explained its delay in adding the charge. The court rejected Zakhari’s argument that the

court should require evidence, rather than taking the government at its word, and also rejected

Zakhari’s argument that Count 3 came too late, again noting the government’s brief and citing

Goodwin’s proposition that a “prosecutor’s assessment of the proper extent of prosecution may

not have crystallized” before trial. Id. at PID 852 (quoting United States v. Branham, 97 F.3d

835, 850 (6th Cir. 1996)). And the court found that, timeline aside, Zakhari failed to show the

prosecutor had a stake in his pretrial motions, given that “it is unrealistic to presume that a

prosecutor’s response to a pretrial motion is an effort to penalize or deter the defendant” and that

LaDeau involved a successful motion to suppress. Id. at PID 852-53 (quoting Branham, 97 F.3d

No. 22-5328 United States v. Zakhari Page 16

at 850). As to the prosecutor’s conduct in the 2007 case, the court noted that Zakhari cited no

other examples to establish a pattern of vindictiveness and that the case was many years before.

C.

We conclude that the court abused its discretion in failing to require the government to

substantiate its explanations. Zakhari showed enough to presume vindictiveness and thus the

government needed to justify the addition of Count 3 using “objective, on-the-record

explanations.” LaDeau, 734 F.3d at 566 (quoting Bragan, 249 F.3d at 482). It was not enough

to rely on unsupported assertions in the government’s brief.

We start with the reasonableness of the prosecutor’s conduct, the most salient factor in

this case. A court must be careful about presuming vindictiveness in the pretrial context because

prosecutors may “uncover additional information that suggests a basis for further prosecution” or

realize that evidence “has a broader significance.” Goodwin, 457 U.S. at 381. But here the

government concedes there was no “new knowledge or change in circumstances” before adding

Count 3, Oral Arg. 27:50-28:04, and the district court also observed this at sentencing, R. 198,

PID 2298 (“[I]f it was going to be added, it was there all along.”).

We are also wary of new charges “based on the same conduct underlying [a] charge in

the initial indictment,” LaDeau, 734 F.3d at 570, or new charges that stretch the fabric of the

case, see United States v. Eddy, 737 F.2d 564, 572 (6th Cir. 1984) (finding presumption of

vindictiveness “strengthened” when government brought perjury charges and “the perjurious

nature of [the] testimony was not manifest”). In this case, Count 3 was based on conduct that, as

the district observed, appears to be part of the same course of conduct charged in Counts 1 and 2,

and also that the district court recognized was not by its “nature . . . manifest[ly]” an attempt to

produce child pornography, id.

True, because the prosecutor here added an “extra charge[] after the exercise of a

procedural right,” she “arguably act[ed] less vindictively than a prosecutor who substitutes a

more severe charge for a less severe one.” Andrews, 633 F.2d at 454. But that fact alone does

not erase the reasons to presume vindictiveness; it merely means the presumption might be

stronger if a charge had been substituted for something less severe. And in fact, the addition of

No. 22-5328 United States v. Zakhari Page 17

Count 3 does not appear all too different from that scenario because it concerns already-charged

conduct and increases the mandatory minimum by half.4

As for the prosecutorial stake, although “routine[]” pretrial motions do not generally

provide a sufficient basis for vindictiveness, Goodwin, 457 U.S. at 381, “[e]ach situation will

necessarily turn on its own facts,” LaDeau, 734 F.3d at 567 (quoting Andrews, 633 F.2d at 453-

54). To be sure, Goodwin mentions several types of motions—to suppress, challenge the

sufficiency and form of indictment, plead an affirmative defense, request psychiatric services,

obtain access to government files, for a jury trial—and concludes “[i]t is unrealistic to assume

that a prosecutor’s probable response to such motions is to seek to penalize and to deter.”

457 U.S. at 381. But as we have explained, “[t]his list is only illustrative of motions that may

typically be expected to cause the government very little responsive burden.” LaDeau, 734 F.3d

at 568. There is no “inflexible presumption” pretrial, not no possible presumption. Goodwin,

457 U.S. at 381.

In this case, Zakhari made a plausible showing that the prosecutor had a sufficient stake

in deterring his pretrial motions, especially his motion to suppress. Zakhari filed a substantial

number of pretrial motions, all but one of which the government strongly opposed, and the

suppression motion presented a grave threat to the prosecution’s case, much like the suppression

motion in LaDeau. At stake was footage of Zakhari confessing to knowing that “boredcrbgirl”

was fifteen and it was wrong to invite her to have sex because she was underage. As noted, “[a]

confession is like no other evidence,” Fulminante, 499 U.S. at 296, and this video was especially

compelling, given the lurid nature of the alleged crime and Zakhari’s defense that he did not

actually believe “boredcrbgirl” was fifteen. This all makes Zakhari’s motion to suppress more

consequential than “routine” pretrial motions, even successful motions that force the government

to redo its work, because the government would have been highly motivated here to protect the

evidence and faced a much tougher trial without it. See LaDeau, 734 F.3d at 568 (explaining

that, in United States v. Moon, “although the government was forced to return twice to the grand

4

We also note that Count 3 did not arise from plea negotiations, a scenario in which “the prosecution may

legitimately threaten to bring harsher charges in order to induce a defendant into pleading guilty.” LaDeau,

734 F.3d at 569 (citing Bordenkircher v. Hayes, 434 U.S. 357, 363-65 (1978)).

No. 22-5328 United States v. Zakhari Page 18

jury to obtain new indictments, it was able to resuscitate its prosecution on charges identical to

those originally brought in the initial indictment simply by properly alleging an interstate

commerce element” (citing 513 F.3d 527, 533, 536 (6th Cir. 2008)).5

To be sure, LaDeau is not on all fours with this case. The government here still had the

Kik messages, so the government’s case would not have been “eviscerated” without Zakhari’s

confession in the same way as in LaDeau, where the defendant successfully suppressed any

evidence that he possessed child pornography, 734 F.3d at 569. It was also highly persuasive in

LaDeau that the motion succeeded and forced the government to start “from scratch,” whereas

here the motion had not yet been decided, id.6

However, we still find LaDeau compelling. Even if its original case was dealt a “mortal

blow,” the government in LaDeau pivoted to a new theory with relative ease, using evidence

already in its possession. 734 F.3d at 569. And although the government here faced only the

immediate burden of responding to the motion to suppress, the many parallels between LaDeau

and this case nevertheless suggest a sufficient prosecutorial stake.7 Cf. Andrews, 633 F.2d at 454

(noting that a “prosecutor’s interest in deterring a bail motion is not as great as a prosecutor’s

interest in deterring appeals to a trial de novo” because “[a] prosecutor who loses a bail motion

does not have to retry a case” but emphasizing that “we cannot accept . . . that the prosecutorial

stake in a pretrial setting is always so de minimus that there can never be a ‘realistic likelihood of

5

The facts in this case also contrast with Goodwin, in which the Supreme Court found that the prosecutor

had an insufficient stake in deterring the defendant from pursuing a jury trial. 457 U.S. at 383. Although “a jury

trial is more burdensome than a bench trial,” id., a jury trial does not deprive the government of pivotal evidence,

thereby requiring the government to reconsider its theory of the case.

6

Apart from the issue of prosecutorial stake, we also note that, in LaDeau, we affirmed a finding of

vindictiveness, and here we consider whether the district court abused its discretion in finding no vindictiveness.

However, the district court here seemed to feel it had very little discretion at all, R. 198, PID 2297 (expressing with

seeming regret that the “standard for [vindictiveness] is just incredibly high”), and we have previously reversed a

district court’s decision finding no vindictiveness, see Eddy, 737 F.2d at 572.

7

It is also worth remembering that Zakhari’s motion to suppress came amid numerous, non-trivial pretrial

motions, almost all of which the government strongly opposed, and at least one motion (the motion to compel

appearance of the decoy officer) was necessarily tied to the suppression motion.

No. 22-5328 United States v. Zakhari Page 19

vindictiveness’”). The fact that Zakhari’s motion to suppress had not yet been decided does not

undermine that the prosecution understood what was at stake.8

Additionally, we stress that the prosecutor’s stake is only part of the equation and must be

considered alongside reasonableness to decide whether “a realistic likelihood of vindictiveness

exists.” Goodwin, 457 U.S. at 373. For example, in Suarez, where we found no presumption

raised by a motion to suppress, we considered that the new charge was not unreasonable because

it arose amid plea negotiations and was based on new evidence. See 263 F.3d at 479-80. And in

LaDeau, we found precedent on the prosecutorial-stake issue less persuasive because there was

“little reason to suspect that the prosecutor’s view of LaDeau’s case changed significantly

between the two indictments.” 734 F.3d at 568. Here, seven months passed between the first

indictment and the second, which increased Zakhari’s potential mandatory minimum sentence by

five years, and there was no “new knowledge or change in circumstances.” Oral Arg. 27:50-

28:04. This was enough, combined with a serious challenge to the government’s case, to raise a

presumption of vindictiveness that required the district court to conduct a more searching

inquiry.

The district court’s statements at sentencing give the sense that it too felt there was a risk

of vindictiveness but not enough to strike Count 3 because it found that the “standard for

[vindictiveness] is just incredibly high and so difficult to prove.” R. 198, PID 2297. As the

district court put it, Count 3 could “have been added at the very beginning of the case” and “if it

was going to be added, it was there all along.” Id. at 2298. Although there is a high bar to prove

vindictiveness, part of what makes clearing that bar difficult is that, in the instance of

presumptive vindictiveness, the government has the opportunity to rebut the presumption. This

is not to say that the threshold to establish a presumption is not high too—it is, particularly in the

pretrial setting—but Zakhari showed enough.

Given Zakhari’s showing, the government had the burden to rebut “the presumption with

‘objective, on-the-record explanations.’” LaDeau, 734 F.3d at 566 (quoting Bragan, 249 F.3d at

8

This all said, we are not persuaded by Zakhari’s argument about the 2007 case involving the same

prosecutor. We do not dismiss the possibility that a prosecutor’s prior conduct may be informative when looking for

vindictiveness, but Zakhari’s example is unhelpful, given it was one event many years before.

No. 22-5328 United States v. Zakhari Page 20

482). By relying on unsupported assertions without permitting Zakhari to test them, the court

abused its discretion. This is especially so because, according to the government’s assertions,

the prosecutor decided to add Count 3 exactly around the time Zakhari filed his suppression

motion, and although the prosecutor reconsidered Zakhari’s case while reviewing several related

cases, the charging decision for “consistency” affected only Zakhari and one other defendant

who was not yet charged. To be clear, we do not reach the ultimate question of vindictiveness;

we simply remand for the district court to reconsider Zakhari’s vindictiveness argument after full

development.

IV.

For the reasons stated, we REVERSE the denial of Zakhari’s motion to suppress,

VACATE his conviction, and REMAND for a new trial and reconsideration of his motion to

dismiss Count 3.

No. 22-5328 United States v. Zakhari Page 21

______________________________

CONCURRENCE / DISSENT

______________________________

KETHLEDGE, Circuit Judge, concurring in part and dissenting in part. I respectfully

disagree with the majority’s conclusion that Joseph Zakhari “clearly” and “unambiguously”

invoked his right to counsel when Detective Hedden asked him whether he wanted to call his

sister. See Davis v. United States, 512 U.S. 452, 459-60 (1994). True, in response to that

question, Zakhari answered—in part—“Yeah”. But the majority reasons as if the “Yeah” were

followed by a period. It was not: instead, Zakhari answered, “Yeah I mean sh—”, followed by a

four-second pause during which he hung his head, looked at the floor, and exhaled.

Hedden had good reason to think that answer was equivocal, not least because it was

incomplete. The phrase “I mean” is most commonly used when a speaker intends to clarify,

qualify, or otherwise amend what he has just said. See “I Mean”, Cambridge Dictionary Online,

https://dictionary.cambridge.org/dictionary/english/i-mean (last visited on October 18, 2023)

(defining “I mean” as an idiom “used to correct what you have just said or to add more

information”). And the interrogation video makes clear that Zakhari’s statement—in both tone

and inflection—was indecisive and uncertain. That is presumably why Hedden tried to clarify

Zakhari’s statement, and why Hedden explained that, if Zakhari wanted to call his sister, that

would “be the end” of their conversation. Yet even then, Zakhari did not clarify what he

“mean[t.]” As measured by dictionaries and body language alike, therefore, Zakhari’s statement

was ambiguous. See United States v. Hampton, 675 F.3d 720, 727-28 (7th Cir. 2012) (suspect’s

statement “Yeah, I do, but you” followed by a pause was not an unambiguous request for

counsel); United States v. Adams, 820 F.3d 317, 323 (8th Cir. 2016) (suspect’s statement, “Nah, I

don’t want to talk man[,] I mean, I—” was not an unambiguous invocation of the right to remain

silent). Under Davis, Hedden had no obligation to stop questioning Zakhari—and the district

court did nor err when it denied his motion to suppress.

No. 22-5328 United States v. Zakhari Page 22

* * *

I concur fully, however, in the majority’s careful explanation as to why the record in this

case supports a presumption of prosecutorial vindictiveness. By way of context, a federal

prosecutor “is the representative not of an ordinary party to a controversy, but of a sovereignty

whose obligation to govern impartially is as compelling as its obligation to govern at all[.]”

Berger v. United States, 295 U.S. 78, 88 (1935). The obligation to govern impartially concerns,

above all, the state’s exercise of coercive power—meaning its power to deprive its subjects of

life, liberty, or property. A court exercises coercive power through its judgments; in doing so, a

judge’s obligation is to apply the law evenhandedly, without favoritism toward particular parties

or outcomes. A prosecutor exercises coercive power as well: indeed, Robert Jackson said, “[t]he

prosecutor has more control over life, liberty, and reputation than any other person in America.”

Robert H. Jackson, The Federal Prosecutor, Address Delivered at the Second Annual Conference

of United States Attorneys (April 1, 1940). For a court’s power is passive, in the sense that the

court itself cannot initiate a case. A prosecutor’s power is active: “The prosecutor can order

arrests, present cases to the grand jury in secret session, and on the basis of his one-sided

presentation of the facts, can cause the citizen to be indicted and held for trial.” Id. Moreover,

as a practical matter, in many cases the prosecutor not only recommends a particular sentence,

but imposes it—by charging the defendant with an offense that brings a mandatory-minimum

sentence.

As a representative of the state, Berger, 295 U.S. at 88, a prosecutor’s exercise of

coercive power must be impartial. Not in a judicial sense, of course: a prosecutor is an

advocate, and thus can advocate particular outcomes. And a prosecutor cannot avoid exercising

discretion. Prosecutorial resources are limited: and so, every day, prosecutors must decide

whether to forbear from pursuing charges for which the case is solid, or whether to pursue

questionable charges, or whether to pursue ones that, upon conviction, bring a mandatory

minimum. As with a judge, however, a prosecutor’s exercise of coercive power should be

evenhanded—meaning it should be directed by rules, rather than by the prosecutor’s will alone.

Those rules might take into account a suspect’s willingness to plead guilty, for example, or his

recidivism, or exculpatory circumstances, or the gravity of harm to a crime’s victims. In all

No. 22-5328 United States v. Zakhari Page 23

cases those rules should be applied without favoritism or bias; and in some cases those rules are

legally enforceable. Indeed the rule of law itself requires that state coercion be grounded in

rules, not will. Accordingly, as a matter of due process, a prosecutor’s discretion “in deciding

whom to prosecute and which charges to bring is not unfettered.” United States v. LaDeau,

734 F.3d 561, 566 (6th Cir. 2013) (internal quotation marks omitted).

The relevant limitation here is that prosecutorial power may not be exercised

vindictively—meaning that the prosecutor may not punish a defendant “for exercising a

protected statutory or constitutional right.” United States v. Goodwin, 457 U.S. 368, 372 (1982).

In Zakhari’s case, the original indictment reflected a prosecutorial judgment that, for the conduct

at issue, a mandatory-minimum sentence of ten years was enough. Yet seven months later—

based on the very same conduct, but after Zakhari’s counsel had filed a battery of motions in his

defense—the prosecution chose to bring an additional charge, which the district court regarded

as a stretch, and which brought a mandatory minimum of 15 years. That decision, on this record,

reflected a “reasonable likelihood of vindictiveness[.]” Id. at 373. And to rebut that inference,

the government was required to offer more than mere assertions in its briefs. The prosecution is

entitled to no deference on questions of fact. Instead, the prosecution must come forward with

evidence—which the district court, in the first instance, can find credible or not.