                                                                                    FILED
                                                                        United States Court of Appeals
                      UNITED STATES COURT OF APPEALS                            Tenth Circuit

                             FOR THE TENTH CIRCUIT                            October 18, 2018
                         _________________________________
                                                                            Elisabeth A. Shumaker
                                                                                Clerk of Court
UNITED STATES OF AMERICA,

      Plaintiff - Appellee,
                                                             No. 17-1370
v.                                                (D.C. No. 1:15-CR-00272-REB-12)
                                                            (D. Colorado)
DANIEL LOPEZ, a/k/a Droopy,

      Defendant - Appellant.
                      _________________________________

                             ORDER AND JUDGMENT *
                         _________________________________

Before BRISCOE, KELLY, and McHUGH, Circuit Judges.
                   _________________________________


       Daniel Lopez pleaded guilty to conspiring to distribute methamphetamine. In

exchange, the government agreed, among other things, that it would recommend his

federal sentence run concurrently with Mr. Lopez’s state sentences. Mr. Lopez claims he

was deprived of the benefit of that bargain. Although the prosecutor at his sentencing

hearing nominally recommended that Mr. Lopez’s sentence run concurrently to any other

sentences, the recommendation was unenthusiastic, at best.




       *
         This order and judgment is not binding precedent, except under the doctrines of
law of the case, res judicata, and collateral estoppel. It may be cited, however, for its
persuasive value consistent with Federal Rule of Appellate Procedure 32.1 and
10th Circuit Rule 32.1.
       Mr. Lopez now appeals, asserting—for the first time—that the prosecutor’s tepid

recommendation breached the plea agreement. Because he failed to make this argument

to the district court, we review only for plain error. And because Mr. Lopez is unable to

show there is a reasonable probability that, but for the alleged error, the result of the

proceeding would have been different, he cannot prevail under a plain error analysis.

Therefore, we affirm the district court’s judgment.

                                   I.   BACKGROUND

       The facts are not in dispute. Mr. Lopez is a career drug dealer who has accrued

five felony drug convictions. In this case, he pleaded guilty to conspiring to distribute

methamphetamine. The government agreed to a 243-month sentence in a Rule

11(c)(1)(C) plea agreement. The government agreed to “recommend this sentence run

concurrent[ly] with any other pending or imposed sentence.” ROA vol. 3, at 9.

       The district court accepted Mr. Lopez’s guilty plea at a March 2016 change-of-

plea hearing. For reasons not apparent from the record, the sentencing hearing was not

held until October 2017, and a different attorney appeared on behalf of the government.

       At the sentencing hearing, the district court asked whether the government wished

to be heard on the appropriate sentence. The new prosecutor chose to make a statement.

In the course of doing so, he cast aspersions on the parties’ plea deal—making sure to

distance himself from his predecessor’s agreement—but at least nominally recommended

that Mr. Lopez’s sentence run concurrently with any other pending or imposed sentence:

              Now, the Court is well aware I did not negotiate this plea agreement,
       and I am bound by the terms, obviously, under those terms, but that’s what

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       I’m bound to do. I would note this individual is getting a very sweet deal, a
       very sweet deal for the nature of his conduct. . . .

              ....

              Now, with respect to the ultimate sentence imposed, obviously
       we’ve agreed to a 243-month sentence. That’s what I’m going to
       recommend. The plea agreement sets out in paragraph 5 of the addendum,
       and I quote, ‘The Government further agrees it will recommend the
       sentence run concurrent with any other pending or imposed sentence.
       Obviously, however, this recommendation will not be binding on the
       Court.’

              Because of that, I do feel bound to recommend that the 32 months
       defense counsel spoke about be taken off and the seven other months in the
       Adams County case that defense counsel referenced also be taken off of the
       sentence. I feel duty bound to do that. I’m honoring the language of the plea
       agreement. Whether or not I negotiated that is a different story. Because I
       am bound by that, that’s what I will honor because I never want to be
       viewed as breaching a plea agreement. I will also make th[e]
       recommendation it be lessened by 39 months and bring it down to a
       sentence of 206 months, if my math is correct.

               I want the Court to understand the Government’s perspective about
       who sits before them. An individual who has been a committed drug
       trafficker his entire life, criminal conduct his entire life and, in the
       Government’s view, has not changed. Thank you.

ROA vol. 4, at 19–20.

       Mr. Lopez’s counsel did not object to the prosecutor’s comments. And at no time

did Mr. Lopez or his counsel argue to the district court that the prosecutor breached the

plea agreement. The district court sentenced Mr. Lopez to 243 months’ imprisonment.

Notwithstanding the government’s recommendation, the court ordered that the federal

sentence would run consecutively to any previously imposed sentences. Once again,

Mr. Lopez did not object.




                                             3
       This appeal followed. Exercising jurisdiction pursuant to 28 U.S.C. § 1291, we

affirm the district court’s judgment under plain error review.

                                     II.   ANALYSIS

                                 A. Standard of Review

       “Where the government obtains a guilty plea predicated in any significant degree

on a promise or agreement with the prosecuting attorney, such a promise must be fulfilled

to maintain the integrity of the plea.” United States v. Hand, 913 F.2d 854, 856 (10th Cir.

1990). Generally, “[w]hether government conduct has violated a plea agreement is a

question of law which we review de novo.” United States v. Brye, 146 F.3d 1207, 1209

(10th Cir. 1998) (quotation marks omitted). “To determine whether a breach has, in fact,

occurred, we apply a two-step process: (1) we examine the nature of the government’s

promise; and (2) we evaluate this promise in light of the defendant’s reasonable

understanding of the promise at the time the guilty plea was entered.” Id. at 1210. “The

government owes the defendant a duty to pay ‘more than lip service’ to a plea

agreement.” United States v. Cachucha, 484 F.3d 1266, 1270 (10th Cir. 2007) (quoting

United States v. Saxena, 229 F.3d 1, 6 (1st Cir. 2000)). “We will not allow the

government to rely upon a rigidly literal construction of the language of the agreement to

escape its obligations under the agreement.” Brye, 146 F.3d at 1210 (internal quotation

marks omitted). “A plea agreement may be breached when ‘[t]he government’s

attorney . . . [i]s not only an unpersuasive advocate for the plea agreement, but, in effect,

argue[s] against it.’” Cachucha, 484 F.3d at 1270 (alterations in original) (quoting United

States v. Grandinetti, 564 F.2d 723, 727 (5th Cir. 1977)).
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       Because Mr. Lopez’s counsel did not object to the alleged breach of the plea

agreement, “appellate-court authority to remedy the error . . . is strictly circumscribed,”

Puckett v. United States, 556 U.S. 129, 134 (2009), and we review only for plain error,

United States v. Bullcoming, 579 F.3d 1200, 1205 (10th Cir. 2009). “Plain error occurs

when there is (1) error, (2) that is plain, which (3) affects substantial rights, and which (4)

seriously affects the fairness, integrity, or public reputation of judicial proceedings.”

United States v. Mendoza, 698 F.3d 1303, 1309 (10th Cir. 2012) (quotation marks

omitted). “Meeting all four prongs is difficult, ‘as it should be.’” Puckett, 556 U.S. at 135

(quoting United States v. Dominguez Benitez, 524 U.S. 74, 83 n.9 (2004)).

                                      B. Discussion

   1. Waiver

       Mr. Lopez’s opening brief requested de novo review. In response, the government

principally argues that “[b]y failing to argue for plain error review, [Mr.] Lopez has

waived the issue that he raises on appeal.” Appellee’s Br. at 3. Alternatively, the

government argues Mr. Lopez is unable to meet the first three prongs of plain error

review.

       “Generally, the failure to argue for plain error and its application on appeal marks

the end of the road for an argument for reversal not first presented to the district court.”

United States v. Kearn, 863 F.3d 1299, 1313 (10th Cir. 2017) (internal quotation marks

omitted), cert. denied, 138 S. Ct. 2025 (2018). Although normally arguments not made in

an opening brief are deemed waived, we have said that a criminal defendant’s

“advancement of a plain error argument in [a] reply brief is sufficient to permit us to

                                              5
consider the argument under plain error review.” United States v. Chavez-Morales, 894

F.3d 1206, 1214 (10th Cir. 2018).

       Mr. Lopez filed an optional reply brief, in which he addressed the standard of

review in the first paragraph:

       Even under a plain-error review standard, the result is the same as it would
       be under a de novo standard: the Government breached the plea agreement.
       The District Court’s allowance of the Government to breach the plea
       agreement was [1] an error, [2] an error which was plain, [3] it affected Mr.
       Lopez’ substantial rights including his due process rights and right to a jury
       trial, and [4] the Government’s obvious breach of the plea agreement with
       its deprivation of Mr. Lopez’ rights had a clear and serious adverse impact
       on the fairness, integrity and public reputation of judicial proceedings.

Appellant’s Reply Br. at 1. This formulaic recitation of the four prongs of plain-error

review is nearly the entirety of Mr. Lopez’s plain-error argument. His reply brief does not

use the words “plain” or “substantial” again until the last paragraph of his argument:

       Regardless of the standard of review, whether de novo or plain error, the
       result is the same. The Government [1] breached the plea agreement, and in
       so doing the Government [3] violated Mr. Lopez’ substantial rights
       including his constitutional rights. The breach violated Lopez’ due process
       rights under the Fifth Amendment to the United States Constitution, and
       given the fact that Lopez waived his right to a jury trial under the plea
       agreement, the Government’s breach thereof violated [Mr.] Lopez’ Sixth
       Amendment right to a jury trial.

Id. at 6–7.

       We are unconvinced Mr. Lopez managed to sufficiently “argue for plain error and

its application,” even in his reply brief. Kearn, 863 F.3d at 1313 (emphasis added); see

also United States v. Mejia-Rios, ___F. App’x ___, 2018 WL 3385373, at *5 (10th Cir.

July 11, 2018) (holding that appellant waived his arguments on appeal where plain-error

review applied and that he did not “adequately address[ ] all four plain-error prongs”).

                                             6
But even if Mr. Lopez had adequately briefed his plain error argument, he cannot prevail

on the merits.

   2. Plain-Error

        To prevail on plain error review, Mr. Lopez must meet each prong of the plain

error analysis: that there is (1) error, (2) that is plain, which (3) affects substantial rights,

and which (4) seriously affects the fairness, integrity, or public reputation of judicial

proceedings. In the absence of any one of these factors, his claim fails. See United States

v. Gantt, 679 F.3d 1240, 1246 (10th Cir. 2012) (“Because all four requirements [of plain

error] must be met, the failure of any one will foreclose relief and the others need not be

addressed.”). Here, we need not decide whether the government plainly violated

Mr. Lopez’s plea agreement (thus satisfying prongs one and two), because Mr. Lopez is

unable to “show that this breach violated his substantial rights.” Mendoza, 698 F.3d at

1310.

        “An error only affects substantial rights when it is prejudicial, meaning that there

is a reasonable probability that, but for the error claimed, the result of the proceeding

would have been different.” Id. (quotation marks omitted). Mr. Lopez asserts the alleged

breach affected his “substantial rights including his due process rights and right to a jury

trial.” Appellant’s Reply Br. at 1. Later, he clarifies that the government’s conduct

“violated [Mr.] Lopez’ due process rights under the Fifth Amendment . . . , and given the

fact that [he] waived his right to a jury trial under the plea agreement, the Government’s

breach thereof violated [his] Sixth Amendment right to a jury trial.” Id. at 7–8. Mr.

Lopez’s arguments, however, fail to address the relevant issue—whether in the absence

                                                7
of the challenged error, “the result of the proceeding would have been different.”

Mendoza, 698 F.3d at 1310. By invoking the Sixth Amendment, Mr. Lopez appears to

suggest that, had the district court concluded the government breached the plea

agreement, he would have been relieved of his guilty plea and may have exercised his

right to a jury trial. But that argument misapprehends the focus of our inquiry. “[T]he

question with regard to prejudice is not whether [the appellant] would have entered the

plea had he known about the future violation. When the rights acquired by the defendant

relate to sentencing, the ‘outcome’ he must show to have been affected is his sentence.”

See Puckett, 556 U.S. at 142 n.4 (citation omitted). Mr. Lopez’s argument is also

inconsistent with his request for relief—that we reverse his sentence and remand for

resentencing.

       Here, the appropriate question under prong three of the plain error analysis is

whether “there is a reasonable probability that, but for the error claimed,” Mendoza, 698

F.3d at 1310, Mr. Lopez’s sentence would have been lower. Mr. Lopez has not even

attempted to make that showing. Nor could he, for the record belies any “reasonable

probability” that the sentencing court would have imposed “a lesser sentence absent the

government’s breach.” Id. The sentencing court expressly and emphatically explained

that it viewed the sentence imposed as barely acceptable, even with the federal and state

sentences imposed to run consecutively:




                                             8
            I struggled about whether or not to approve this plea agreement. 243
      months[1] for this crime committed by this criminal? The sentence is almost
      criminal. . . .

            Well, I'm going to approve the plea agreement, and I’m going to
      impose a sentence of 243 months as the parties negotiated, as the parties
      agreed, and I’ll hold my nose as I do that. . . .

               ....

              Here, the sentence has to focus on the seriousness of the offense at
      issue. 243 months barely satisfies that statutory requirement and need. . . .

               ....

             So in terms of punishing the seriousness of the offense, promoting
      respect for the law, protecting the public from additional crimes of
      Mr. Lopez, which is both predicted and predictable, in deterring not only
      Mr. Lopez, but others who are similarly situated and inclined, and to avoid
      sentencing disparities within this case itself because I’ve now sentenced
      over a dozen of the other co-defendants in this case, I’ve listened to the
      evidence presented during the trial of defendant No. 13, Mr. Jorge Loya-
      Ramirez. For that, I exercise my discretion to impose a sentence of 243
      months consecutively to any previously imposed sentence . . . . Only a total
      sentence of 243 months comes close to satisfying and vindicating the
      important needs and requirements of the federal sentencing statute at 18
      U.S.C. Section 3553(a). Even a day less is an insult to that federal
      sentencing statute.

ROA vol. 4, at 24–26 (emphases added).

      For Mr. Lopez to prevail, we must be convinced there exists a “reasonable

probability” that Mr. Lopez would have received a lower sentence from this judge had

the prosecutor not breached the plea agreement. “[A] reasonable probability is a

probability sufficient to undermine confidence in the outcome.” United States v.

Bustamante-Conchas, 850 F.3d 1130, 1138 (10th Cir. 2017) (en banc) (quotation marks


      1
          Mr. Lopez’s guideline range was 324 to 405 months.

                                            9
omitted). On this record there is no reasonable probability that Mr. Lopez would have

received a lower sentence had the district court heard a more enthusiastic

recommendation for concurrent sentences from the government. See Mendoza, 698 F.3d

at 1310 (holding that there was no reasonable probability of a lesser sentence where the

sentencing court “was quite clear that it considered [the sentence imposed] to be ‘a

bargain, relatively speaking’”). Where, as here, the challenged error “did not ‘affec[t]

substantial rights,’ the Court of Appeals ha[s] no authority to correct it.” United States v.

Olano, 507 U.S. 725, 741 (1993). Mr. Lopez’s challenge fails on the third prong of plain-

error review.

                                   III. CONCLUSION

       For the above reasons, we uphold the district court’s acceptance of Mr. Lopez’s

plea and AFFIRM its judgment.

                                               Entered for the Court


                                               Carolyn B. McHugh
                                               Circuit Judge




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