United States of America v. Manuel Estrada-Gonzalez

RECOMMENDED FOR PUBLICATION
Pursuant to Sixth Circuit I.O.P. 32.1(b)
File Name: 22a0085p.06
UNITED STATES COURT OF APPEALS
FOR THE SIXTH CIRCUIT
UNITED STATES OF AMERICA,
Plaintiff-Appellee,
v.
MANUEL ESTRADA-GONZALEZ,
Defendant-Appellant.
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No. 22-3001
Appeal from the United States District Court for the Northern District of Ohio at Cleveland.
No. 1:21-cr-00390-1—John R. Adams, District Judge.
Decided and Filed: April 26, 2022
Before: ROGERS, KETHLEDGE, and MURPHY, Circuit Judges.
_________________
COUNSEL
ON BRIEF: Christian J. Grostic, OFFICE OF THE FEDERAL PUBLIC DEFENDER,
Cleveland, Ohio, for Appellant. Rebecca Chattin Lutzko. UNITED STATES ATTORNEY’S
OFFICE, Cleveland, Ohio, for Appellee.
_________________
OPINION
_________________
MURPHY, Circuit Judge. Suppose a prosecutor told a district court that “a sentence at
the top of a defendant’s guidelines range was at least appropriate under the relevant sentencing
factors, if not required by them.” The court would likely understand the prosecutor to be arguing
that such a sentence was legally permissible and perhaps even legally compelled. Now suppose
that the prosecutor told the court that “a sentence at least at the top of the defendant’s guidelines
range was appropriate.” The court would likely take the prosecutor to be arguing that such a
>

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sentence was the minimally acceptable one and that an above-guidelines sentence might also be
justified.
This case requires us to consider which of these two ideas the prosecutor
conveyed during Manuel Estrada-Gonzalez’s sentencing for illegally reentering the country.
Estrada-Gonzalez claims that the prosecutor impliedly recommended an above-guidelines
sentence by stating that a sentence at the “high end of the sentencing guideline range would be at
the least appropriate in this case.” Sent. Tr., R.29, PageID 140. He thus argues that the
prosecutor breached the parties’ plea agreement, which barred her from “suggest[ing] in any
way” that the court should vary above the guidelines range. Agreement, R.16, PageID 67. Yet
the district court that heard this ambiguous statement in real time rejected Estrada-Gonzalez’s
reading of it, finding instead that the prosecutor had been advocating only “for a sentence at the
high range of the guidelines.” Sent. Tr., R.29, PageID 146. And while our precedent instructs us
to review the ultimate question whether a prosecutor’s conduct breached a plea agreement de
novo, see United States v. Warren, 8 F.4th 444, 448 (6th Cir. 2021), we clarify in this case that
we must review any subsidiary findings about the historical facts under the deferential clear-error
standard. What the prosecutor expressed with her statement is that type of fact question.
Because the district court did not clearly err in its resolution of the question, the government did
not breach the plea agreement. We thus affirm.
I
Born and raised in Guatemala, Estrada-Gonzalez first entered the United States as a
teenager with his father. In December 2001, shortly after a Missouri court convicted a then-adult
Estrada-Gonzalez of forgery, the government removed him to Guatemala. Twenty years later,
Estrada-Gonzalez came to the attention of the authorities in northeast Ohio when the mother of
his longstanding girlfriend called the police on him. According to police reports, Estrada-
Gonzalez’s girlfriend told the officers who arrived on the scene that he had gotten intoxicated
and threatened to kill her (as he had done frequently in the past). The reports noted further that
Estrada-Gonzalez had possessed a machete while making these threats. He had fled the scene
when the officers arrived, but they successfully arrested him on domestic-violence charges and
seized the machete.

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The federal government soon indicted Estrada-Gonzalez for illegally reentering the
United States following his earlier deportation, in violation of 8 U.S.C. § 1326. He pleaded
guilty to this reentry crime. In the plea agreement, Estrada-Gonzalez and the government both
agreed to recommend that the district court impose a sentence within the applicable guidelines
range. The agreement added: “Neither party will recommend or suggest in any way that a
departure or variance is appropriate, either regarding the sentencing range or regarding the kind
of sentence.” Agreement, R.16, PageID 67.
At the start of the sentencing hearing, though, the district court told the parties that it was
contemplating an upward variance from Estrada-Gonzalez’s guidelines range. The court and the
parties agreed that Estrada-Gonzalez faced a guidelines range of 6 to 12 months’ imprisonment.
But the court then expressed concern with the claims in the police reports, describing how they
suggested that Estrada-Gonzalez had threatened to kill his girlfriend and burn their house down
with their children in it.
Following its summary of the reports, the court asked for the government’s position on
the proper sentence. The prosecutor pointed out that the state had dismissed Estrada-Gonzalez’s
domestic-violence charges because the federal government had taken custody of him. Sent. Tr.,
R.29, PageID 138. She next played a portion of an officer’s body-camera footage from the night
of Estrada-Gonzalez’s arrest to give the court a “clear understanding” of what had happened and
to show the “present sense impressions of” those involved. Id., PageID 139–40. After airing the
video, the prosecutor noted that a sentence at the top of the guidelines range “would be at the
least appropriate”:
I realize that the statutory maximum is 20 years based on his prior forgery
conviction from Missouri in 2001 prior to being deported. However, with the
sentencing guideline range, it is between 6 to 12 months, I do realize he has since
served seven months and four days incarcerated on this case, but based off the
circumstances, and clearly I would echo [the court’s] sentiments in regards to the
safety of not only the wife, the children, as well as the mother and her boyfriend,
who reside in the house, certainly a high end of the sentencing guideline range
would be at the least appropriate in this case.
Id., PageID 140.

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Ultimately, the court chose to vary upward from Estrada-Gonzalez’s guidelines range.
It relied primarily on Estrada-Gonzalez’s history of threatening violence against his family.
Finding Estrada-Gonzalez’s conduct “deeply troubling,” the court opined that this conduct made
his case stand out from the typical illegal-reentry case. Id., PageID 143–44. The court thus
chose an 18-month term of imprisonment, one that was six months above the top end of Estrada-
Gonzalez’s guidelines range.
The court ended the hearing by asking the parties whether they had any final objections.
See United States v. Bostic, 371 F.3d 865, 872 (6th Cir. 2004). Defense counsel argued that the
government had violated the plea agreement by advocating for a sentence “at least at the high
end of the guidelines range[.]” Sent. Tr., R.29, PageID 146. This argument, counsel suggested,
implied that an above-guidelines sentence might be appropriate. Id. But the plea agreement
barred the government from suggesting “in any way” that the court should vary above the
guidelines range. Id.
The district court overruled the objection. The court “did not interpret [the prosecutor’s]
statement to mean anything other than the government’s lawyer is asking for a sentence at the
high range of the guidelines.” Id. It found that defense counsel was “misstating or
misconstruing” the statement. Id. The prosecutor then made “clear” that she had been
advocating for a sentence at the top of the guidelines range, not above it. Id., PageID 147.
II
Estrada-Gonzalez renews his argument that the government breached the plea agreement
by impliedly advocating for an above-guidelines sentence. The ground rules for this argument
are well established. Our plea-agreement precedent blends a mix of contract principles with a
mix of constitutional ones. Like any agreement with consideration on both sides, a plea
agreement is “essentially” a contract between the defendant and the government. Puckett v.
United States, 556 U.S. 129, 137 (2009); see, e.g., Warren, 8 F.4th at 448; United States v.
Ligon, 937 F.3d 714, 718 (6th Cir. 2019); United States v. Lukse, 286 F.3d 906, 909 (6th Cir.
2002). Courts thus have looked to the common law of contracts to help resolve such issues as
whether a plea agreement contained a particular term, see United States v. Robison, 924 F.2d

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612, 613–14 (6th Cir. 1991), or whether the government’s breach of the agreement voided it, see
Puckett, 556 U.S. at 137.
Unlike an ordinary agreement, however, a plea agreement implicates the constitutional
protections for criminal defendants in our Bill of Rights. See Mabry v. Johnson, 467 U.S. 504,
509 (1984); United States v. Barnes, 278 F.3d 644, 647–48 (6th Cir. 2002). Because a defendant
who pleads guilty waives such things as the Sixth Amendment right to a jury trial, the
Constitution (not just the contract) requires the government to live up to the promises that it uses
to induce the defendant to waive these rights. See Barnes, 278 F.3d at 647–48; see also
Santobello v. New York, 404 U.S. 257, 262–63 (1971); cf. Philip Hamburger, Purchasing
Submission: Conditions, Power, and Freedom 44–45, 167 (2021). Federal courts thus have not
treated plea agreements as purely state-law creatures subject solely to state-law contract rules.
They have instead developed a body of federal principles to guide the interpretation and
enforcement of plea agreements. See United States v. Herrera, 928 F.2d 769, 773 (6th Cir.
1991).
How do these federal principles apply to the parties’ disagreement in this case?
Clarifying where their disagreement sits within our caselaw goes a long way toward clarifying its
proper resolution. In some of our cases, the defendant and the government have disagreed over
whether they entered into a plea agreement at all (e.g., they dispute whether they reached an oral
contract) or whether the agreement contained a particular term (e.g., they dispute whether the
government agreed not to take a position on the appropriate sentence). See, e.g., Ramos v.
Rogers, 170 F.3d 560, 564 (6th Cir. 1999); Herrera, 928 F.2d at 773; Baker v. United States,
781 F.2d 85, 88–90 (6th Cir. 1986). Consistent with the common law of contracts, we have
treated these “contract-formation” questions as factual issues for the district court subject to
deferential clear-error review. See United States v. Quesada, 607 F.3d 1128, 1131 (6th Cir.
2010); Robison, 924 F.2d at 614; see also 11 Williston on Contracts § 30:3 (4th ed.), Westlaw
(database updated Nov. 2021).
Here, however, the parties agree on these basic contract-formation facts. Both sides
signed a written agreement. See Agreement, R.16, PageID 73. And both sides agree that this

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contract included a provision that prohibited the government from “suggest[ing] in any way” that
the district court should impose an upward variance. Id., PageID 67.
In some of our other cases, the parties have conceded that the plea agreement contained a
particular term, but they have disputed what that term means (e.g., they dispute whether the term
should be read to require the government to seek a downward departure). See, e.g., United States
v. Ricks, 398 F. App’x 135, 137 (6th Cir. 2010); United States v. Fitch, 282 F.3d 364, 365–67
(6th Cir. 2002). Again consistent with common-law contract principles, we have treated the
question whether an agreement’s language is unambiguous as a legal issue subject to de novo
review. See Fitch, 282 F.3d at 366; see also Restatement (Second) of Contracts § 212(2) & cmt.
d (Am. L. Inst. 1981). When interpreting that language, moreover, we have focused on how a
“reasonable person” would understand it—just as a court would with any contract. United States
v. Moncivais, 492 F.3d 652, 663 (6th Cir. 2007); see also 11 Williston on Contracts, supra,
§ 30:6. And if we find the language ambiguous, we have held that the agreement’s meaning
becomes a fact question that turns on the parties’ intent. See Ricks, 398 F. App’x at 137; see also
Restatement (Second) of Contracts § 212(2) & cmt. e. But the government will face an uphill
battle at this point. At the end of the interpretive process, we typically resolve any ambiguities in
a defendant’s favor because of the agreement’s effect on the defendant’s constitutional rights.
See Warren, 8 F.4th at 448; Fitch, 282 F.3d at 367–68; United States v. Johnson, 979 F.2d 396,
399 (6th Cir. 1992).
Here, however, the parties agree on the meaning of the relevant provision. By
prohibiting the government from “suggest[ing]” an upward variance “in any way,” Agreement,
R.16, PageID 67, the agreement unambiguously committed the government to a “sweeping
promise,” Warren, 8 F.4th at 449. As we have explained when interpreting the same language in
another agreement, this clause did not just bar the government from expressly advocating for an
above-guidelines sentence. See id. at 448–49. The clause also meant that the government could
not “in any way ‘mention [a variance] as something to think over,’ ‘bring [a variance] to the
mind for consideration,’ ‘propose’ or ‘mention’ a variance ‘as a possibility,’ or put a variance
‘forward by implication.’” Id. (quoting Webster’s New World College Dictionary 1450 (Sparks
et al. eds., 5th ed. 2020) and Webster’s Third New International Dictionary 2286 (2002)).

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In still other cases, the parties have not disputed the law (what does the contractual term
mean?) or the facts (what did the government do?). Rather, they have disputed whether the
undisputed historical facts (e.g., the government’s failure to expressly request a sentence at the
low end of the guidelines range) rose to the level of a “breach” of the unambiguous contractual
term (e.g., a term requiring the government to recommend such a sentence). See Barnes,
278 F.3d at 646–48. We have repeatedly treated such questions about whether a party has
breached a plea agreement as questions of law subject to de novo review. See, e.g., Warren,
8 F.4th at 448; Barnes, 278 F.3d at 646; United States v. Wells, 211 F.3d 988, 995 (6th Cir.
2000). That standard comports with background common-law principles, which indicate that
“the issue of whether a party to a contract has breached a contractual provision is . . . a question
of law” when “there is no controversy over the facts[.]” 23 Williston on Contracts, supra,
§ 63:15. Considering the question’s constitutional pedigree, this standard also comports with
Supreme Court precedent that has reviewed similar constitutional questions (such as whether
probable cause exists) de novo. See U.S. Bank Nat’l Ass’n ex rel. CWCapital Asset Mgmt. LLC
v. Vill. at Lakeridge, LLC, 138 S. Ct. 960, 967 n.4 (2018) (citing Ornelas v. United States,
517 U.S. 690, 697 (1996)).
Warren provides a good example of this type of dispute. There, like here, the agreement
indicated that the prosecutor would not suggest an upward variance in any way. See 8 F.4th at
448–49. At sentencing, however, the prosecutor explained that the government had not known
that the defendant’s prior convictions involved shootings. Id. at 446–47. The prosecutor went
on to opine that the government “likely would have made a different recommendation had it
known [the defendant] shot at multiple people.” Id. at 449. Neither the prosecutor nor the
defendant found any ambiguity in this statement: the prosecutor plainly indicated that, in
retrospect, the government would not have recommended a guidelines sentence if it had
possessed all relevant information when entering the plea deal. Id. So we had to decide whether
this unambiguous comment conflicted with the unambiguous agreement not to suggest an
upward variance in any way—a question that we reviewed de novo. Id. at 448–49. In the end,
we held that the statement violated the agreement because the government brought the idea of a
variance “forward by implication” and implied that it did not believe that a guidelines sentence
was appropriate. Id.

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Estrada-Gonzalez suggests that his case falls within Warren’s category of disputes.
He argues that the facts are undisputed, that we must review the district court’s conclusion
de novo, and that the prosecutor suggested by implication that the court should impose an
above-guidelines sentence. But Estrada-Gonzalez misclassifies his case. In Warren, the parties
did not dispute the meaning of the prosecutor’s statements, so we opted to resolve ourselves the
question whether the undisputed facts rose to the level of a breach of the unambiguous provision.
Id. at 448–51. This case, by contrast, hinges on a disputed factual question about what the
prosecutor actually conveyed. Recall again her words: “certainly a high end of the sentencing
guideline range would be at the least appropriate in this case.” Sent. Tr., R.29, PageID 140.
This statement admits of two meanings. On the one hand, the prosecutor’s statement
might be taken to convey that a high-end guidelines term would be the lowest appropriate
sentence, implying that an above-guidelines sentence would also be appropriate. One meaning
of “at the least” could support this view in the abstract. According to Estrada-Gonzalez, the
prosecutor’s use of this adverbial phrase conveyed the idea that the top-of-the-guidelines
sentence was the “lowest possible” length, thereby impliedly suggesting that a sentence “more
than” that length (an above-guidelines sentence) would also be proper. American Heritage
Dictionary of the English Language 1000 (5th ed. 2018); Cambridge Dictionary, available at
https://dictionary.cambridge.org/us/dictionary/english/at-least (last visited Apr. 14, 2022); see
also United States v. Diaz-Jimenez, 622 F.3d 692, 696 (7th Cir. 2010). If the prosecutor
expressed this message, she would have breached the agreement. Cf. Warren, 8 F.4th at 448–49.
On the other hand, this statement might be interpreted to mean that a top-of-the-
guidelines sentence was at a minimum permissible under a proper balancing of the sentencing
factors in 18 U.S.C. § 3553(a)—if not required by that balancing. As the government points out,
the prosecutor did not use the phrase “at the least” to modify the length of the sentence (the way
in which Estrada-Gonzalez reads her statement). Rather, she used that phrase to modify
“appropriate”—that is, “suitable” or “fitting.” American Heritage, supra, at 88. To suggest that
a top-of-the-guidelines sentence was at a minimum “suitable” could be read to imply nothing
more than that it might also be required. Nobody, for example, would have thought that the
prosecutor impliedly advocated for an above-guidelines sentence if she had said that the top-of-

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the-guidelines sentence was “required by the § 3553(a) factors or at the least permitted by them.”
If her statement were interpreted in this way, moreover, she would not have breached the
agreement.
So which version should we choose? As an appellate court that can review only the
words on the transcript page, we are poorly positioned to decide what the prosecutor conveyed
with this ambiguous commentary. See Anderson v. City of Bessemer City, 470 U.S. 564, 575
(1985). Yet the district court was ideally positioned to answer that question because it had the
opportunity to listen to her live. See id.; Marshall v. Lonberger, 459 U.S. 422, 434 (1983). Its
choice between the two interpretations, for example, might have rested in part on the
prosecutor’s pauses and inflection when making the statement. Perhaps Estrada-Gonzalez’s
reading might be more likely if the prosecutor had emphasized the phrase “at the least,” whereas
the government’s might be more likely if she had emphasized the word “appropriate.” In other
words, the correct resolution of this question might turn on the “crucial human element” that
only the district court had the ability to assess. United States v. Sheron, 787 F. App’x 332, 333
(6th Cir. 2019).
These considerations lead us to conclude that the parties’ dispute in this case falls within
a category different from Warren—one that turns on a district court’s resolution of the
“historical” facts about what happened (separate from its application of the law to the facts).
United States v. Thomas, 933 F.3d 605, 610 (6th Cir. 2019) (quoting U.S. Bank, 138 S. Ct. at
966). To be sure, we have for decades generically said that we review de novo the question
whether the prosecutor breached the plea agreement. See Wells, 211 F.3d at 995. But, like the
other circuit courts to consider this question, we do not think that this standard should cover the
subsidiary question of “what are the facts,” United States v. Moscahlaidis, 868 F.2d 1357, 1360
(3d Cir. 1989), which includes “what the parties said or did,” United States v. Martin, 25 F.3d
211, 217 (4th Cir. 1994) (citation omitted). Rather, we must review a district court’s findings
about these historical facts under the deferential clear-error standard. See Martin, 25 F.3d at 217;
Moscahlaidis, 868 F.2d at 1360; see also United States v. Clark, 55 F.3d 9, 11 (1st Cir. 1995);
cf. United States v. Pollard, 959 F.2d 1011, 1024 (D.C. Cir. 1992). This conclusion comports
with basic contract-law principles—as courts unsurprisingly review factual findings for clear

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error in that setting too. See, e.g., Dillon v. Cobra Power Corp., 560 F.3d 591, 599 (6th Cir.
2009); 23 Williston on Contracts, supra, § 63:15.
The district court, moreover, did not clearly err by finding that the prosecutor conveyed
only that the government recommended a sentence at the high end of the guidelines range. Sent.
Tr., R.29, PageID 146. The deferential clear-error standard requires us to defer to the district
court’s finding about what transpired “even if we would have made [the] opposite finding,” so
long as both stories are plausible on the record as a whole. United States v. Caston,
851 F. App’x 557, 560 (6th Cir. 2021); see also Cooper v. Harris, 137 S. Ct. 1455, 1468 (2017).
The court’s finding clears this low bar. On its own terms, the prosecutor’s statement could
reasonably be read to imply nothing more than that the requested top-of-the-guidelines sentence
was required, not just permitted. Sent. Tr., R.29, PageID 140. The prosecutor also made the
statement in response to Estrada-Gonzalez’s argument that the court should impose a sentence of
time served (7 months). Id. It thus arose in the context of a debate about whether the court
should impose a bottom-of-the-guidelines sentence, further distancing it from any upward-
variance suggestion. Cf. United States v. Mason, 410 F. App’x 881, 889 (6th Cir. 2010). The
district court also correctly recognized that Estrada-Gonzalez’s counsel, when making this
objection, “misconstru[ed]” the prosecutor’s statement to suggest that she had argued for a
sentence “at least at the high end of the guideline range[.]” Sent. Tr., R.29, PageID 146.
By subtly changing the word that “at the least” modified, counsel fundamentally transformed the
nature of the statement. And the prosecutor herself later clarified the ambiguity by indicating
that she had meant to ask only for a top-of-the-guidelines sentence. Id., PageID 147. The record
thus plausibly supported the district court’s finding.
Estrada-Gonzalez responds that we must interpret ambiguities in the plea agreement in
his favor. See Warren, 8 F.4th at 448. But this case does not contain an ambiguous plea
agreement. We accept Estrada-Gonzalez’s broad reading of it. The case instead contains an
ambiguous record. So this presumption of contract interpretation has no relevance here.
That may be so, Estrada-Gonzalez next argues, but we have also indicated that
prosecutors should be held to “meticulous standards of performance.” Moncivais, 492 F.3d at
662 (quoting United States v. Vaval, 404 F.3d 144, 152–53 (2d Cir. 2005)). Estrada-Gonzalez

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misreads this statement to the extent he argues that it compels a district court to find the
underlying facts in a defendant’s favor whenever the evidence could cut both ways. The
statement means only what we said in Warren: “The government cannot escape its duties under a
plea agreement with a wink and a nod.” 8 F.4th at 449. Under the district court’s findings of
fact in this case, though, neither a wink nor a nod occurred. The government fully performed as
promised.
We affirm.

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