Opinion ID: 4513537
Heading Depth: 2
Heading Rank: 1

Heading: Counsel’s Plea-Related Conduct

Text: Mr. Orozco first argues that Ms. Strickland was ineffective in counseling him about the plea agreement. He asserts that her performance was deficient and that he was prejudiced because he agreed to a binding plea agreement that he would not otherwise have accepted.1 Like the district court, we focus on Strickland’s prejudice prong. See Strickland, 466 U.S. at 697 (noting that a court may focus first on either prong and need not examine both if one is not satisfied).
To place Mr. Orozco’s argument in context, we survey relevant decisions regarding prejudice in the guilty-plea context. We start with Hill. There, after establishing that Strickland applies to challenges to guilty pleas based on ineffective 1 Mr. Orozco also suggests he suffered prejudice from Ms. Strickland’s failure to negotiate a better plea agreement. But he neither identifies where he made this argument in the district court nor explains why this court should entertain an argument made for the first time on appeal. See United States v. Moya, 676 F.3d 1211, 1213 (10th Cir. 2012) (defendant “did not raise these matters in district court and has not provided a reason to deviate from the general rule that we do not address arguments presented for the first time on appeal” (internal quotation marks omitted)). 10 assistance of counsel, Hill, 474 U.S. at 58, the Court held that the prejudice prong “focuses on whether counsel’s constitutionally ineffective performance affected the outcome of the plea process,” id. at 59. Thus, when the defendant asserts he would not have pleaded guilty if counsel had advised him correctly, “to satisfy the ‘prejudice’ requirement, the defendant must show that there is a reasonable probability that, but for counsel’s errors, he would not have pleaded guilty and would have insisted on going to trial.” Id. In Flores-Ortega, 528 U.S. at 474, counsel failed to file a notice of appeal. Consistent with Hill, because “counsel’s alleged deficient performance arguably led not to a judicial proceeding of disputed reliability, but rather to the forfeiture of a proceeding itself,” the Court imposed a presumption of prejudice. Id. at 483. “[W]e cannot accord any presumption of reliability . . . to judicial proceedings that never took place.” Id. (internal quotation marks omitted). To perfect a showing of prejudice in this context, a defendant must demonstrate a reasonable probability that, had counsel not performed deficiently, he would have timely appealed. See id. at 484, 486. Next, in Padilla v. Kentucky, 559 U.S. 356, 359 (2010), defense counsel incorrectly advised a lawful permanent resident regarding the immigration consequences of a guilty plea. The Court noted that as part of establishing prejudice in these circumstances, a defendant “must convince the court that a decision to reject the plea bargain would have been rational under the circumstances.” Id. at 372. 11 Two years later, Missouri v. Frye, 566 U.S. 134, 139 (2012), presented the opposite circumstances to Mr. Orozco’s case—there, counsel failed to communicate a plea offer to the defendant, who later entered an open plea and received a higher sentence. After holding that defense counsel has the duty to communicate plea offers to the client, id. at 145, the Court directed that, to show prejudice where a plea offer lapsed or was rejected, defendants must demonstrate a reasonable probability that (1) they would have accepted the earlier offer had they been afforded effective assistance, (2) the prosecution would not have canceled the plea and the court would have accepted it, and (3) “the end result of the criminal process would have been more favorable by reason of a plea to a lesser charge or a sentence of less prison time.” Id. at 147. In Frye’s companion case, Lafler v. Cooper, 566 U.S. 156, 160 (2012), a defendant rejected a plea offer on the inaccurate advice of counsel, was convicted at trial, and received a higher sentence than he would have under the plea agreement. Thus, “[h]aving to stand trial, not choosing to waive it, [was] the prejudice alleged.” Id. at 163-64. The Court rejected the idea that a constitutionally adequate trial necessarily resulted in a lack of prejudice: “Even if the trial itself is free from constitutional flaw, the defendant who goes to trial instead of taking a more favorable plea may be prejudiced from either a conviction on more serious counts or the imposition of a more severe sentence.” Id. at 166. As in Frye, therefore, Lafler held that to establish prejudice in those circumstances, defendants must show a reasonable probability that they would have accepted the plea agreement, the prosecution would 12 not have withdrawn it and the court would have accepted it, “and that the conviction or sentence, or both, under the offer’s terms would have been less severe than under the judgment and sentence that in fact were imposed.” Id. at 164. In Lee v. United States, 137 S. Ct. 1958, 1963 (2017), the defendant’s primary concern was avoiding deportation, and he pleaded guilty based on counsel’s erroneous advice that the conviction would not support deportation. Looking to Hill, the Court emphasized that where a defendant is entirely deprived of a judicial proceeding, the prejudice inquiry “focuses on a defendant’s decisionmaking, which may not turn solely on the likelihood of conviction after trial.” Id. at 1966. “In the unusual circumstances” before the Court, Mr. Lee established prejudice by demonstrating a reasonable probability that he would have rejected the plea, even though his chances of acquittal were slim. Id. at 1967. “The decision whether to plead guilty also involves assessing the respective consequences of a conviction after trial and by plea. When those consequences are, from the defendant’s perspective, similarly dire, even the smallest chance of success at trial may look attractive.” Id. at 1966 (citation omitted). “[W]here we are . . . asking what an individual defendant would have done, the possibility of even a highly improbable result may be pertinent to the extent it would have affected his decisionmaking.” Id. at 1967. Most recently, in Garza v. Idaho, 139 S. Ct. 738, 742, 747 (2019), the Court held that the Flores-Ortega presumption of prejudice applies even where a defendant has signed an appeal waiver as part of his plea agreement. “[T]his Court has made clear that when deficient counsel causes the loss of an entire proceeding, it will not 13 bend the presumption-of-prejudice rule simply because a particular defendant seems to have had poor prospects.” Id. at 747 (citing Lee, 137 S. Ct. at 1966-67).

Mr. Orozco relies on Lee, asserting that he need show only a reasonable probability that but for counsel’s errors he would not have entered the same plea and that such a decision would have been rational. Thus, he faults the district court for relying on Frye and requiring him to show a reasonable probability that entering an open plea would have resulted in a lower sentence. But we agree with the district court that Frye is the more applicable precedent in these circumstances. Lee, like Hill, Flores-Ortega, and Garza, addresses circumstances in which a defendant was entirely deprived of a proceeding—the defendants in Lee and Hill of a trial, and the defendants in Flores-Ortega and Garza of an appeal. But Mr. Ortega does not claim that he would have proceeded to trial had he been counseled accurately; instead, he asserts that he would have entered an open guilty plea rather than accepting the government’s plea offer. Based on Mr. Orozco’s own description of what he would have done, he was not entirely deprived of a proceeding. Either way, he would have entered a guilty plea. Thus, this case is more like one “involving mere attorney error,” in which “we require the defendant to demonstrate that the errors actually had an adverse effect on the defense.” Flores-Ortega, 528 U.S. at 482 (internal quotation marks omitted); see also Strickland, 466 U.S. at 693 (“Even if a 14 defendant shows that particular errors of counsel were unreasonable, . . . the defendant must show that they actually had an adverse effect on the defense.”). Analogizing to Mr. Lee’s primary interest in avoiding deportation, see Lee, 137 U.S. at 1963, Mr. Orozco submits that he had a primary interest in having his imperfect duress defense adequately presented to the court. The record, however, does not support an inference that Mr. Orozco had an interest in presenting the duress argument for its own sake. Rather, the argument was merely a means of achieving his ultimate goal of the lowest possible sentence. This ultimate goal—lowering the sentence—distinguishes Mr. Orozco’s circumstances from Lee, where the length of the sentence was collateral to Mr. Lee’s primary goal of avoiding deportation. See id. at 1967. In these circumstances, Frye is the more analogous precedent. Like this case, Frye involved two competing guilty pleas, one under a plea offer and the other an open plea. See Frye, 566 U.S. at 139. Consistent with Hill, the Frye Court could have required the defendant to show nothing more than a reasonable probability that he would have accepted the earlier-offered plea agreement instead of entering an open plea. But it chose to go beyond that requirement, also specifically making it “necessary to show a reasonable probability that the end result of the criminal process would have been more favorable by reason of a plea to a lesser charge or a sentence of less prison time.” Id. at 147. Although Mr. Orozco’s circumstances are the inverse of those in Frye, the Court’s determination that a more favorable outcome 15 is a necessary component of the analysis logically extends to this competing-plea scenario as well. For these reasons, we agree with the district court that to establish prejudice, Mr. Orozco must show a reasonable probability that entering an open guilty plea would have been more favorable to him than continuing with the plea agreement.
Under the plea agreement, Mr. Orozco faced a sentence of 63 to 78 months. He was sentenced to 72 months. Without the plea agreement, he would have faced a sentence of 77 to 96 months. So to satisfy the more-favorable-result requirement, he must show a reasonable probability that the district court would have departed or varied downward had he entered an open plea. As stated above, “[a] reasonable probability is a probability sufficient to undermine confidence in the outcome.” Strickland, 466 U.S. at 694. In determining whether he made this showing, we consider all the circumstances of the case. Id. at 695. And we recognize that the evaluation “should proceed on the assumption that the decisionmaker is reasonably, conscientiously, and impartially applying the standards that govern the decision” and “should not depend on the idiosyncracies of the particular decisionmaker, such as unusual propensities toward harshness or leniency.” Id. But Mr. Orozco discusses his various grounds for a downward departure or variance only with regard to whether he would have entered an open plea, how the district court erred in considering its own subjective views, and how the arguments would have altered his decision-making. He does not argue how these grounds 16 establish a reasonable probability that he would have received a lower sentence had he entered an open plea. His failure to adequately address this issue in his opening brief results in a waiver on appeal. See Baca v. Berry, 806 F.3d 1262, 1276 (10th Cir. 2015). Even if Mr. Orozco had adequately briefed this issue, however, we would conclude that he did not establish prejudice. He identifies the following grounds for a downward departure or variance: (1) the “outsized impact” a 17-year-old prior conviction had on the offense level and criminal-history category, Opening Br. at 58-59; (2) his nonviolent criminal history, which distinguishes him from others in criminal-history category VI; (3) the unfairness of adding points for committing the instant offense while under supervised release from the prior conviction, because after his sentencing the relevant Guideline was amended to suggest that a defendant subject to deportation not be sentenced to supervised release; and (4) his imperfect-duress defense. With respect to the first two grounds, we agree with the district court that “the totality of Mr. Orozco-Sanchez’s criminal history,” particularly his repeated illegal entries into the United States, would “weigh[] against granting a significant departure or variance.” R. at 634. Notwithstanding their nonviolent nature, Mr. Orozco’s violations were numerous: in addition to the 17-year-old 1998 conviction for alien smuggling, he accrued convictions for illegal reentry in 2000, 2005, and 2011. Of particular importance, the sentence in his 2011 case was 63 months, and that was not 17 sufficient to deter him from illegally reentering two weeks after he was released from prison in 2015. We also strongly doubt that the supervised-release argument would have been persuasive at sentencing. As Mr. Orozco acknowledges, the Guideline was amended after he was sentenced. Thus, he had been properly subjected to a term of supervised release, which he did in fact violate. And finally, we agree with the district court that there is no reasonable probability that the imperfect-duress defense would have resulted in a sentence lower than the 72 months Mr. Orozco received. The defense was implausible (he asserted in 2011 as an excuse for his reentry that drug cartels wanted to kill him, and in 1998 he gave the excuse that he was forced at knifepoint to transport aliens). And it was contradicted by Mr. Orozco’s admission under oath that he had knowingly and voluntarily reentered the United States. We therefore affirm the denial of relief on this ineffective-assistance claim.