United States Court of Appeals
For the First Circuit
No. 22-1423
UNITED STATES OF AMERICA,
Appellee,
v.
DEREK MUÑOZ-GONZALEZ,
Defendant, Appellant.
APPEAL FROM THE UNITED STATES DISTRICT COURT
FOR THE DISTRICT OF PUERTO RICO
[Hon. Silvia L. Carreño-Coll, U.S. District Judge]
Before
Gelpí, Lipez, and Rikelman,
Circuit Judges.
José R. Olmo-Rodríguez, for appellant.
Gregory B. Conner, Assistant United States Attorney, with
whom W. Stephen Muldrow, United States Attorney, and Mariana E.
Bauzá-Almonte, Assistant United States Attorney, Chief, Appellate
Division, were on brief, for appellee.
July 17, 2025
GELPÍ, Circuit Judge. Derek Muñoz-Gonzalez ("Muñoz")
was indicted on multiple charges related to child pornography,
including two counts of production, one count of possession, and
one count of distribution. He agreed to plead guilty to two counts
of producing child pornography. The plea agreement contained,
among other provisions, a waiver-of-appeal clause setting forth
Muñoz's waiver of his right to appeal "any aspect of this case" if
the court sentenced him to a term of imprisonment of 327 months or
less.
At the sentencing hearing, the district court sentenced
Muñoz to 327 months. He appealed, claiming that the prosecutor
breached the plea agreement by advocating for two enhancements
that were not included in the agreement's sentencing guidelines
calculation and asserting that the agreement's waiver-of-appeal
clause does not preclude him from raising that breach claim. We
disagree. Because the prosecutor did not breach the plea
agreement, we affirm.
I. BACKGROUND
A. Facts
We briefly recount the relevant facts and travel of the
case. In January 2021, an undercover Federal Bureau of
Investigation ("FBI") agent identified a person suspected of being
a child molester through Kik Messenger ("Kik"), a mobile messaging
application frequently used for exchanging child pornography.
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That person was Muñoz, a resident of Puerto Rico. Via Kik, Muñoz
said he was sexually exploiting his own then-eight-month-old
daughter. Another Kik user asked Muñoz in a Kik group chat, "[D]o
you play with your daughter?" "I have," Muñoz responded. After
disclosing in the chat that his daughter was under a year old,
Muñoz shared a picture of a baby lying on a bed with an adult
female standing in front of her.
This prompted the undercover officer to begin
communicating with Muñoz privately. In their conversation, Muñoz
admitted he had been a pedophile for a long time. He also sent
the officer images and videos of child sexual abuse and said he
had been sexually active with his eight-month-old daughter. Muñoz
also offered to share photos of his girlfriend's fifteen-year-old
sister, whom he had photographed while she was in the bathroom.
The next day, on January 12, 2021, Muñoz posted another
message in a Kik group chat, stating that he took additional
pictures and videos of his daughter earlier that day. He shared
a video and two pictures, which collectively depicted Muñoz
sexually abusing his infant daughter. As a result, the FBI sent
an emergency disclosure request to Kik to obtain Muñoz's
demographic information and investigate further. And, after
Muñoz's identity was corroborated, he was arrested.
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B. Procedural History
Two weeks after Muñoz's arrest, a federal grand jury
charged him in a four-count indictment with (1) production of child
pornography of an eight-month-old infant, in violation of 18 U.S.C.
§ 2251(a) and (e) (Count I); (2) production of child pornography
of a fifteen-year-old female minor, also in violation of
18 U.S.C.
§ 2251(a) and (e) (Count II); (3) distribution of child
pornography, in violation of
18 U.S.C. § 2252(a)(2) (Count III);
and (4) possession of child pornography, in violation of
18 U.S.C.
§ 2252(4)(B) (Count IV). Muñoz subsequently pleaded guilty only
to Counts I and II, each of which carries a term of imprisonment
of fifteen to thirty years. In return, the government agreed to
dismiss Counts III and IV.
The plea agreement stipulated an advisory guideline
range of 262 to 327 months' imprisonment. Said guideline range
accounted for the following offense-level enhancements: (1) the
victims' ages, (2) the knowing distribution of the images and
videos, and (3) the familial relationship between Muñoz and the
victims. The guideline calculations also accounted for Muñoz's
acceptance of responsibility for his behavior. The parties agreed
that Muñoz could request a sentence of 262 months of imprisonment
while the government could recommend one of up to 276 months'
imprisonment. Any petition by either party for a term of
imprisonment below or above that stipulated sentence
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recommendation, the agreement stated, would "constitute a material
breach of the Plea Agreement."
Notably, the agreement also contained a clause waiving
Muñoz's right to appeal:
[Muñoz] knowingly and voluntarily agrees that, if the
imprisonment sentence imposed by the Court is 327 months
or less, [he] waives the right to appeal any aspect of
this case's judgment and sentence, including, but not
limited to the term of imprisonment or probation,
restitution, fines, forfeiture, and the term and
conditions of supervised release.
At the sentencing hearing, Muñoz's counsel asked the
district court to impose a sentence of 262 months' imprisonment,
arguing that such sentence would be sufficient, but not greater
than necessary to punish, deter, and rehabilitate Muñoz. The
government countered that 276 months' imprisonment was a more
appropriate sentence to deter others, protect the public, and
reflect the seriousness of Muñoz's conduct.
In advocating for its position, the government
highlighted two facts stipulated in the plea agreement: (1) Muñoz
had sexual contact with his infant daughter and (2) the images and
videos he sent to others in the Kik chat depicted sexual abuse of
an infant. These two facts, although stipulated in the plea
agreement's factual summary, were not factored into the parties'
proposed guidelines calculation.
At sentencing, the district court considered the
stipulated facts spelled out in the plea agreement, which included
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the fact that Muñoz "used the application Kik to share videos and
images of him[self]" having sexual contact with his
eight-month-old daughter. And after considering the stipulated
facts along with the sentencing guidelines, the district court
ultimately sentenced Muñoz to 327 months of imprisonment -- a
longer sentence than either party had recommended at the sentencing
hearing, but within the waiver-of-appeal limit.1 Believing that
the government did not hold up its end of the bargain, Muñoz
appealed.
II. DISCUSSION
Muñoz advances two arguments on appeal. First, he argues
that the waiver-of-appeal provision in the plea agreement does not
bar this appeal because that provision only encompasses challenges
to the court's imposition of a sentence, not arguments that the
government breached the plea agreement. Second, Muñoz contends
that the prosecutor breached the plea agreement when she
highlighted conduct excluded from the stipulated guidelines
calculation: (1) the sexual contact he had with his infant daughter
and (2) the sharing of images and videos with others on Kik,
depicting him sexually abusing his infant daughter. Because we
hold that the prosecutor did not breach the plea agreement, we
1The sentence imposed was also within the applicable
sentencing guidelines range.
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need not address whether the waiver-of-appeal clause bars this
appeal.
This court reviews de novo a defendant's claim that the
prosecutor breached the plea agreement. See United States v.
Almonte-Nuñez, 771 F.3d 84, 89 (1st Cir. 2014); see also United
States v. Rivera-Ruiz,
43 F.4th 172, 179 (1st Cir. 2022). But
when the "defendant has knowledge of conduct ostensibly amounting
to a breach of a plea agreement, yet does not bring that breach to
the attention of the sentencing court" during sentencing, this
court reviews for plain error. Rivera-Ruiz,
43 F.4th at 179
(quoting United States v. Rivera-Rodríguez,
489 F.3d 48, 57 (1st
Cir. 2007)). At the sentencing proceeding, Muñoz failed to assert
that the prosecutor breached the plea agreement. Thus, we review
Muñoz's submission under plain error.
"The defendant's burden under the plain error standard
is a heavy one." United States v. Umeh, 132 F.4th 573, 582 (1st
Cir. 2025) (citation omitted). This rigorous standard requires
Muñoz to show "(1) that an error occurred (2) which was clear or
obvious and which not only (3) affected [his] substantial rights,
but also (4) seriously impaired the fairness, integrity, or public
reputation of judicial proceedings." United States v.
Ruiz-Huertas,
792 F.3d 223, 226 (1st Cir. 2015) (alteration in
original) (citation omitted). To make that showing, however, the
defendant has only one avenue: the opening brief. It is in the
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opening brief where the defendant must address each prong of the
plain-error standard. For this court has said time and again "that
an argument at best entitled to plain error review [is] waived
where the appellant made no attempt to satisfy that standard in
his opening brief." United States v. Mulkern, 49 F.4th 623, 636
(1st Cir. 2022) (citation modified). Indeed, "[u]nder the plain
error doctrine, if an error is not properly preserved,
appellate-court authority to remedy the error is strictly
circumscribed." United States v. Pabon,
819 F.3d 26, 33 (1st Cir.
2016) (citation modified).
Here, Muñoz failed to expressly address the plain-error
standard in his opening brief. Although he sought to address the
standard in his reply brief, our precedent is clear "that issues
advanced for the first time in an appellant's reply brief are
deemed waived." Waste Mgmt. Holdings, Inc. v. Mowbray, 208 F.3d
288, 299 (1st Cir. 2000); see also United States v.
Rodriguez-Monserrate,
22 F.4th 35, 40 (1st Cir. 2021); United
States v. Rodríguez-Torres,
939 F.3d 16, 40 & n.14 (1st Cir. 2019).
For this reason alone, Muñoz waived his breach-of-plea-agreement
claim.
But in any event, even setting waiver aside, the
government's comments at sentencing did not constitute "a clear or
obvious breach of the plea agreement." United States v. Davis,
923 F.3d 228, 239 (1st Cir. 2019). To demonstrate "'clear or
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obvious error,' a party must show that the error is contrary to
existing law." United States v. Rabb, 5 F.4th 95, 101 (1st Cir.
2021) (citation omitted). That law or principle must also be
clearly established in our precedent. See United States v.
Espinoza-Roque,
26 F.4th 32, 36 (1st Cir. 2022) ("An appellant
cannot establish plain error using 'case law absent clear and
binding precedent.'" (quoting United States v. Marcano, 525 F.3d
72, 74 (1st Cir. 2008) (per curiam))). "In other words, the error
must be 'indisputable' in light of controlling law." Rabb,
5 F.4th
at 101 (quoting United States v. Jones,
748 F.3d 64, 69-70 (1st
Cir. 2014)). If our precedent does not clearly establish the
error, then the appellant cannot overcome the plain error hurdle.
See
id.
In the plea agreement context, "[w]hen a plea rests in
any significant degree on a promise or agreement of the prosecutor,
so that it can be said to be part of the inducement or
consideration, such promise must be fulfilled." United States v.
Lessard, 35 F.4th 37, 42 (1st. Cir. 2022) (citation omitted).
"Because plea bargaining requires defendants to waive fundamental
constitutional rights, we hold prosecutors engaging in plea
bargaining to the most meticulous standards of both promise and
performance."
Id. (citation modified). These "standards require
more than lip service to, or technical compliance with, the terms
of a plea agreement."
Id. (quoting Almonte-Nuñez, 771 F.3d at
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89). Since "[a] defendant is entitled to the benefit of the
bargain struck in the plea deal and to the good faith of the
prosecutor," id. (citation modified), a prosecutor cannot make
"end-runs around" the promises in the plea agreement, United States
v. Castillo,
126 F.4th 791, 796 (1st Cir. 2025) (citation omitted).
On the other hand, "we recognize that the government is
not obliged to present an agreed-upon recommendation with ruffles
and flourishes." Id. (citation modified). "Nor do we require"
the prosecution to display "any particular degree of enthusiasm"
when making its sentencing recommendation.
Id. (citation
omitted). While there is no "magic formula" for assessing a
prosecutor's performance, we must consider the "totality of the
circumstances" in asking whether their conduct was "reasonably
consistent" with the recommendation they promised. Lessard,
35
F.4th at 42 (citation omitted); see also United States v.
Acevedo-Osorio,
118 F.4th 117, 128 (1st Cir. 2024) (stating that
the court "must examine the totality of the circumstances in a
case-by-case approach" by considering the "'net effect of the
government's behavior' to determine whether, on balance, it has
'undermine[d] the benefit of the bargain.'" (alteration in
original) (quoting United States v. Cortés-López,
101 F.4th 120,
128 (1st Cir. 2024))). And so, "[b]ecause context is key, we have
declined to find breach where a prosecutor's comments come at the
'court's urging' or 'in direct response to defense counsel's
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attempt to put an innocent gloss' on relevant facts." Castillo,
126 F.4th at 796 (quoting United States v. Saxena,
229 F.3d 1, 7
(1st Cir. 2000)).
During the sentencing hearing, the prosecutor
recommended 276 months of imprisonment, as agreed in the plea
agreement. At the beginning of her allocution, the prosecutor
affirmed that "the United States stands by the plea
agreement . . . ascribed by the parties," and that "[p]ursuant to
that plea agreement, the United States is requesting a sentence of
276 months of imprisonment." Then, in explaining why 276 months
was a more appropriate sentence than a 262-month sentence, the
prosecutor stated that one of the victims was an infant and that
certain images and videos involved sexual acts or contact with the
victim. Those facts were stipulated in the plea agreement. And
the context in which the prosecutor offered them suggests that she
simply reminded the court of the stipulated record to counter the
focus on Muñoz's "history and characteristics" in defense
counsel's allocution for a more lenient sentence. In the end, the
prosecutor reaffirmed that the United States "stand[s] by [its]
recommendation of 276 months of imprisonment."
It is far from obvious that the prosecutor's emphasis on
the stipulated facts constituted advocacy for enhancements not
contained in the plea agreement. See United States v.
Miranda-Martinez, 790 F.3d 270, 274 (1st Cir. 2015) ("[T]he
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government's review of the facts of the case cannot constitute a
breach of the plea agreement when they are relevant to the court's
imposition of sentence." (citation modified)). To the contrary,
the record makes plain that the prosecutor explained why her
sentencing recommendation was appropriate in response to Muñoz's
recommendation for a lesser sentence. See United States v.
Cruz-Vázquez, 841 F.3d 546, 549 (1st Cir. 2016) ("Having
unequivocally stated that it was recommending a sentence at the
higher end of the guideline range, the government was free to offer
reasons supporting its recommendation.").
"When the parties agree that a defendant may argue for
a particular sentence while the government may argue for a somewhat
stiffer sentence," the government is not constrained to pull its
punches when arguing for the stiffer sentence. United States v.
Montañez-Quiñones, 911 F.3d 59, 65 (1st Cir. 2018). Our precedent
has made clear that "when the plea agreement allows the government
to advocate for a sentence that is stiffer than the sentence that
defense counsel has proposed, the government 'ha[s] a right
(indeed, a duty) to explain to the court why the higher sentence
that it [i]s urging [i]s more appropriate.'" Lessard,
35 F.4th at
43 (alterations in original) (quoting Montañez-Quiñones,
911 F.3d
at 65). We therefore conclude that Muñoz has not clearly shown
that the government breached the plea agreement. Because we hold
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that no breach of the plea agreement occurred, we see no reason to
address Muñoz's remaining contention.
III. CONCLUSION
For the reasons discussed above, we affirm.
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