United States v. Jeronimo 398 F.3d 1149

Opinion by Judge GOULD; Dissent by Judge BERZON.

GOULD, Circuit Judge.

We consider whether a plea agreement is enforceable and effectively waives the right of appeal. We conclude that we are without jurisdiction to assess the merits of this direct appeal.

I

In July 2002, Pascual Dionicio Jeronimo (“Jeronimo”) faced a potential maximum sentence of thirty years imprisonment for various drug trafficking offenses when he entered into plea negotiations with the government. Through his former attorney, John Kolego (“Kolego”), Jeronimo reached a plea agreement on November 1, 2002, whereby the government agreed to dismiss some of his pending charges, recommend downward departure and a sentence at the low end of the applicable guideline range, refrain from seeking an upward departure, and reduce his maximum potential sentence to twenty years. In return, Jeronimo agreed to plead guilty to two counts of drug trafficking, admit to specific drug quantities, forfeit his interest in certain property, and to waive his rights to appeal and to collaterally attack the length of his sentence. Both Jeronimo and Kolego signed the plea agreement. Immediately above Jeronimo’s signature in capital letters was the following statement:

*1151I HAVE READ OR HAD READ AND TRANSLATED TO ME IN SPANISH BY AN INTERPRETER, THIS AGREEMENT AND HAVE CAREFULLY REVIEWED EVERY PART OF IT WITH MY ATTORNEY.

I UNDERSTAND AND VOLUNTARILY AGREE TO IT AND PROMISE TO ABIDE BY EVERY TERM.

I VOLUNTARILY SIGN THIS AGREEMENT WITH THE FULL UNDERSTANDING OF ALL OF THE ABOVE.

At Jeronimo’s change of plea hearing, which also took place on November 1, 2002, the district court dutifully conducted a comprehensive plea colloquy with Jeroni-mo that embraced all disclosures and inquiries required by Rule 11 of the Federal Rules of Criminal Procedure.1 Among these disclosures was the district court’s explicit advice to Jeronimo that “the maximum penalty [under his plea agreement was] 20 years in prison and a fine of up to $1 million.” Jeronimo in response assured the district court that he had discussed the federal Sentencing Guidelines with Kolego, and that he was satisfied with Kolego’s help. When asked if his plea was “freely and voluntarily made with a good understanding of the nature of the charges against [him] and the matters in [the] plea petition and plea bargain letter,” Jeronimo, said “yes.”

Before the court’s acceptance of the plea, the prosecutor interjected comments alerting Jeronimo that the government was planning to bring .his prior drug and felony assault convictions, as well as his status as an illegal alien and a prison *1152escapee, to the court’s attention during sentencing. When the court asked Jeroni-mo if he understood that these facts would “likely affect [his] sentence,” Jeronimo responded “yes.” The court accepted his plea.

The United States Probation Office issued its Presentence Report and Sentencing Recommendation on December 10, 2002. Because of his previous convictions for felony assault and drug trafficking, Jeronimo was classified as a career offender with an applicable Sentencing Guidelines range of 151-88 months of imprisonment.

On March 6, 2003, Jeronimo moved through Kolego to withdraw his guilty plea on the grounds that “he[did] not believe that he was adequately advised as to the potential sentencing consequences prior to his change of plea and[did] not feel his plea was intelligently and knowingly made.” On March 17, 2003, Jeronimo filed a separate pro se “Motion to Withdraw Plea of Guilty Due to Inadequate and Fraudulent Representation By Legal Counsel” alleging that Kolego “on several occasions distorted facts as well as misled for the purpose of extracting a ‘Guilty’ plea.” He also alleged that Kolego “repeatedly changed and lied about possible sentences after [the] plea of ‘Guilty’ was entered.”

On May 27, 2003, Richard Fredericks (“Fredericks”) was appointed as Jeroni-mo’s new attorney. On August 14, 2003, Fredericks filed a Memorandum in Support of Motion to Withdraw Guilty Plea on Jeronimo’s behalf, asserting that Jeronimo was “deprived ... of the opportunity to make an intelligent and voluntary decision” because he allegedly pleaded in reliance on Kolego’s erroneous prediction that he would receive a sentence of 87 months.

At a hearing on his plea withdrawal motion, Jeronimo testified that he had many discussions with Kolego about “the merits of the plea offer” and the Sentencing Guidelines, and that his “understanding” based on these discussions was that he would receive a sentence of 87 months as Kolego “prediet[ed].” Jeronimo also testified that Kolego never raised the possibility of “career offender” sentencing during any of their discussions and that he would not have accepted the plea offer if he had known that he would receive a sentence of 151 months.

On cross-examination, Jeronimo continued to assert that he had “made a deal” with Kolego, stating: “I trusted in him ... and I signed for 87 months. When I realized that the sentence was longer, if I had realized, if I known that, I wouldn’t have sign[ed] it.” However, he conceded that he entered his plea with the understanding that his sentencing would be up to the judge, not Kolego. Jeronimo also admitted that “the deal that [he] made with his lawyer did not include what this judge was going to sentence [him] to”; that the government had warned him at his change of plea hearing that his prior convictions would be raised at sentencing, and the district court had observed that those facts would “likely affect the extent” of his sentence; that he had pleaded guilty with the understanding that he could receive a sentence of up to twenty years; and that he had received the benefit of his bargain because 151 months was less than twenty years.

In denying Jeronimo’s motion to withdraw his plea, the district court noted that Jeronimo’s argument that his defense attorney “blew the career offender issue” was “made without evidence from the attorney,” and that “even if that was the case ... a perfect attorney doesn’t exist.” This timely appeal followed.

II

We lack jurisdiction to entertain appeals where there was a valid and en*1153forceable waiver of the right to appeal. United States v. Vences, 169 F.3d 611, 613 (9th Cir.1999) (“It would overreach our jurisdiction to entertain an appeal when the plea agreement effectively deprived us of jurisdiction.”). We review de novo whether a defendant has waived his right to appeal by entering into a plea agreement and the validity of such a waiver. United States v. Ventre, 338 F.3d 1047, 1051 (9th Cir.2003). A defendant’s waiver of his appellate rights is enforceable if (1) the language of the waiver encompasses his right to appeal on the grounds raised, and (2) the waiver is knowingly and voluntarily made. United States v. Joyce, 357 F.3d 921, 922 (9th Cir.2004); United States v. Martinez, 143 F.3d 1266, 1270-71 (9th Cir.1998).

A

We first must address the issue of whether Jeronimo’s waiver of his right to appeal precludes his challenge on direct appeal to the district court’s rejection of his request to withdraw his guilty plea, based on his assertion that fair and just reasons supported a change of plea. “Our analysis begins with the fundamental rule that plea agreements are contractual in nature and are measured by contract law standards.” United States v. Clark, 218 F.3d 1092, 1095 (9th Cir.2000) (internal citation and quotation marks omitted). This customary reliance on contract law applies to interpretation of an appeals waiver within a plea agreement, and we will generally enforce the plain language of a plea agreement if it is clear and unambiguous on its face. United States v. Nunez, 223 F.3d 956, 958 (9th Cir.2000); see also Martinez, 143 F.3d at 1271.

In Martinez, the defendant entered into a plea agreement with language similar to that here. The Martinez plea agreement provided that “[a]ny plea of guilty entered by Defendant pursuant to this agreement and any judgment and/ or sentence based thereon ... will not be the subject of legal challenge by Defendant.” 143 F.3d at 1270. In rejecting the defendant’s attempt to appeal his sentence on the grounds that the district court had misapplied the Sentencing Guidelines, we held that the defendant’s “waiver of any ‘legal challenge’ encompasses all appeals on all grounds except for a few narrow exceptions,2 none of which apply here.” Id. at 1271. Similarly, in Nunez we held that an agreement stating that the defendant “knowingly and voluntarily waive[s] his right to appeal any sentence imposed by the Court” constituted an “unmistakable” waiver of the right to appeal. 223 F.3d at 958 (internal quotation marks omitted).

Here, Jeronimo’s agreement provides in pertinent part that:

*1154By accepting the benefits of this agreement and if sentenced by the Court to a term of imprisonment of less than the statutory maximum of 20 years, Mr. Jer-onimo waives any and all rights to appeal, and all his waivable statutory rights to file a petition pursuant to 28 U.S.C. § 2255 challenging the length of his sentence.

This language plainly states that Jeronimo waived his right to appeal his sentence on any and all grounds in exchange for a sentence of less than twenty years and various other benefits under the agreement. Thus, based on Martinez and Nunez, we conclude that Jeronimo’s plea agreement clearly encompasses his right to bring the present appeal.

Jeronimo contends that the waiver language only covers his right to appeal on the grounds that his sentence was improper or violated the terms of the plea agreement; he argues that we have jurisdiction because the waiver does not specifically preclude him from appealing on the grounds that the district court abused its discretion. However, we dismissed a similar argument in United States v. Schuman, 127 F.3d 815, 817 (9th Cir.1997), where the appellant asserted that a plea agreement providing that he “waive[d] ... any right to appeal or collaterally attack the conviction and sentence” did not preclude him from challenging the district court’s application of the federal Sentencing Guidelines because the agreement failed to “specifically address his statutory right to appeal” on that basis. There we stated: “We reject [the appellant’s] contention that the language of the plea agreement does not specifically contemplate the statutory right to appeal incorrect applications of the Sentencing Guidelines for it would render the waiver meaningless.” Id. Accordingly, while Jeronimo’s plea agreement does not specifically contemplate the possibility of an appeal based on the district court’s denial of a motion to withdraw, its broad language clearly bars him from bringing this appeal.

B

Having concluded that Jeronimo’s waiver included the appeal he now advances, we next consider whether his waiver was knowing and voluntary. We follow the rule that a waiver of the right to appeal is knowing and voluntary where the plea agreement as a whole was knowingly and voluntarily made. As we stated in Portillo-Cano:

[WJaivers of appeal must stand or fall with the agreement of which they are a part. If the agreement is voluntary, and taken in compliance with Rule 11, then the waiver of appeal must be honored. If the agreement is involuntary or otherwise unenforceable, then the defendant is entitled to appeal.

192 F.3d at 1250 (internal quotation marks and citation omitted).

At least on its face, the district court’s extensive Rule 11 colloquy with Jeronimo shows that Jeronimo’s plea was knowingly and voluntarily made. The district court properly advised Jeronimo of the nature of the drug charges against him, the consequences of conviction, and the constitutional rights he was waiving by pleading guilty. The district court also summarized each of the terms of Jeronimo’s plea agreement, including the appeal waiver provision, and informed Jeronimo that his maximum possible penalty under the agreement was 20 years imprisonment and a fine of $1 million. Noting that the government would bring “relevant facts” to its attention, the district court further advised Jeronimo that it could depart from the applicable Sentencing Guidelines ranges for various reasons and told him not to rely on sentencing predictions made by others because “the judge decides the sentence.”

*1155Jeronimo responded by acknowledging that he had discussed the Sentencing Guidelines with Kolego, and assuring the district court that his plea was “freely and voluntarily made.” Finally, when the government warned that it would raise Jeroni-mo’s prior convictions and status as an illegal alien and prison escapee at sentencing, the district court asked Jeronimo if he understood that such facts would “likely affect [his] sentence,” and Jeronimo said “yes.”

Nonetheless, Jeronimo claims that his attorney’s failure to advise him of all the possible consequences of a guilty plea deprived him of the information necessary to render his plea — and the waiver of appeal contained therein — truly knowing and voluntary.3

To demonstrate ineffective assistance of counsel, a defendant must show: (1) that his counsel’s performance was deficient;. and (2) that the deficient performance prejudiced his defense. Strickland v. Washington, 466 U.S. 668, 687, 104 S.Ct. 2052, 80 L.Ed.2d 674 (1984). This test applies to challenges to guilty pleas based on ineffective assistance of counsel claims. Hill v. Lockhart, 474 U.S. 52, 58, 106 S.Ct. 366, 88 L.Ed.2d 203 (1985).

We first consider whether counsel Kolego’s performance is shown to be deficient on the record before us. “A defendant who pleads guilty upon the advice of counsel may only attack the voluntary and intelligent character of his guilty plea by showing that the advice he received from counsel was not within the range of competence demanded of attorneys in criminal cases.” United States v. Signori, 844 F.2d 635, 638 (9th Cir.1988). Because of the difficulties in evaluating attorney performance in hindsight, courts considering ineffective counsel claims “indulge a strong presumption that counsel’s conduct falls within the wide range of reasonable professional assistance.” Strickland, 466 U.S. at 689, 104 S.Ct. 2052.

Here, the main thrust of Jeronimo’s ineffective assistance of counsel claim is that his attorney’s failure to consider and inform him of the possibility that he might be sentenced as a career offender constituted a “misrepresentation” that justifies withdrawal of his plea.

A guilty plea cannot be “induced by ... misrepresentation.” Signori, 844 F.2d at 638 (quoting Brady v. United States, 397 U.S. 742, 755, 90 S.Ct. 1463, 25 L.Ed.2d 747 (1970)). We have also held that a defendant who pleads guilty in reliance on his or her attorney’s “gross mischaraeteri-zation of the likely outcome” of his or her case may be entitled to withdraw the plea on ineffective assistance of counsel grounds. Iaea v. Sunn, 800 F.2d 861, 865 (9th Cir.1986); see also U.S. v. Michlin, 34 F.3d 896, 899 (9th Cir.1994) (“We have held that an erroneous prediction by a defense attorney concerning sentencing does not entitle a defendant to challenge his guilty plea, although an exception might be made in a case of gross mischar-acterization of the likely outcome.”) (internal quotation marks and citations omitted).

However, as a general rule, we do not review challenges to the effectiveness of defense counsel on direct appeal. United States v. McKenna, 327 F.3d 830, 845 (9th Cir.2003). Thus, in McKenna, we declined to review an ineffective assistance of counsel claim on direct appeal because we concluded, inter alia, that we could not evaluate the defendant’s claim that counsel should have filed various motions because the “record [wa]s ... not developed with respect to why [the defendant’s] attorneys *1156felt that the motionsfthe defendant] wanted filed were not warranted by the evidence.” Id.

To similar effect i's our decision in United States v. Laughlin, 933 F.2d 786, 788-89 (9th Cir.1991), where a defendant whose probation was revoked brought an ineffective assistance claim on direct appeal and contended that his counsel’s performance during his revocation hearing was so constitutionally deficient as to merit a new hearing. We declined to address the defendant’s claim because “[t]he record contained] little more than generalized assertions of incompetency.” Id. at 789. We stressed that “[flormer defense counsel has had no opportunity to explain his actions” and that the defendant had not “established any foundation for demonstrating that the alleged errors actually prejudiced the outcome of the hearing.” Id.

The rationale for our general rule, as explained in United States v. Birges, 723 F.2d 666, 670 (9th Cir.1984), is that ineffectiveness of counsel claims “usually ... cannot be advanced without the development of facts outside the original record.” Stated another way, a “[c]hallenge [to effectiveness of counsel] by way of a habeas corpus proceeding is preferable as it permits the defendant to develop a record as to what counsel did, why it was done, and what, if any, prejudice resulted.” Laughlin,, 933 F.2d at 788-89.

We have recognized two extraordinary exceptions to this general rule: We have permitted ineffective assistance claims to be reviewed on direct appeal in the unusual cases (1) where the record on appeal is sufficiently developed to permit determination of the issue, or (2) where the legal representation is so inadequate that it obviously denies a defendant his Sixth Amendment right to counsel. United States v. Daychild, 357 F.3d 1082, 1095 (9th Cir.2004).

In these exceptional cases, the reason for our general rule is inapplicable because development of further evidence is unnecessary to assess whether counsel performed below the constitutionally required standard. See, e.g., United States v. Anderson, 850 F.2d 563, 565 n. 1 (9th Cir.1988). But neither of these exceptions apply here; as Jeronimo points out, the record contains no evidence from Kolego. Contrary to the dissent’s argument, we do not suggest that evidence from Kolego is required because he might have made a “strategic decision” not to inform Jeronimo about the career offender issue. Rather, such evidence is necessary because, on the current state of the record, we cannot determine whether Kolego in fact failed to inform Jeronimo about that issue at all. Jeronimo cannot, at this stage on direct appeal, make out an ineffective assistance claim.

In light of the scope of the record on this direct appeal, we cannot now conclude that Jeronimo has shown that his plea agreement, which included an unequivocal waiver of his appeal rights, was involuntary and unenforceable. Further, “we will not remand a case from direct appeal for fact-finding related to an ineffective assistance of counsel claim, but allow a defendant to pursue the issue in district court collateral proceedings.” United States v. Reyes-Platero, 224 F.3d 1112, 1117 (9th Cir.2000).4

*1157III

We lack jurisdiction to entertain this appeal because the appeal waiver in Jeron-imo’s plea agreement is unambiguous and the record as it is currently constituted demonstrate that the agreement was no^ knowingly and voluntarily made.5

APPEAL DISMISSED.

*1158BERZON, Circuit Judge,

dissenting:

On March 17, 2003, Pascual Jeronimo filed a pro se motion to withdraw his guilty plea due to “inadequate and fraudulent representation by [his] attorney.” At the hearing on this motion, Jeronimo, represented by new counsel, was asked whether, “[djuring the conversations with your attorney, did the phrase ‘career offender’ ever come up?” He answered “No, he didn’t tell me anything about that,” and maintained that “I made a deal with my attorney, I trusted in him, sir, and I signed for 87 months. When I realized that the sentence was longer, if I had realized, if I known [sic] that, I wouldn’t have sign [sic] it.” After a hearing that included a lengthy examination and cross-examination of Jeronimo and argument from counsel on both sides, the district court, noting that the accusation that the “defense attorney blew the career offender issue” was made without evidence from the attorney, determined that the truth or falsity of Jeroni-mo’s account did not matter. Rather, said the district court, “even if that was the case” — that is, even if the defense attorney did “bl[o]w the career offender issue” — “a perfect attorney doesn’t exist, and the question is whether a defendant has been properly informed of the range of consequences that could occur” (emphasis added). The district court then denied Jeroni-mo’s motion to withdraw his guilty plea.

As the majority recognizes, the appeal waiver “must stand or fall with the agree*1159ment of which [it is] a part,” and is therefore valid only if the plea agreement itself was knowingly and voluntarily made.1 Ante at 1154 (quoting United States v. Portillo-Cano, 192 F.3d 1246, 1250 (9th Cir.1999)). Citing United States v. Signori, 844 F.2d 635 (9th Cir.1988), the majority also recognizes that attorney misrepresentation or gross mischaracterization can invalidate a guilty plea. Ante at 1155. Given these principles, the validity of the appeal waiver is bound up with the merits question that Jeronimo presents: whether he should have been allowed to withdraw his guilty plea because of erroneous advice by his counsel regarding the applicable sentencing provisions.

Yet, the majority never addresses the crux of this case — whether Jeronimo’s plea was knowingly and voluntarily made in light of his lawyer’s representations. Instead, the majority recites that ineffective assistance claims are generally better suited for collateral review, and ducks the central issue. This decision, made despite the fact that the legal question at issue was raised in and decided by the district court after a full hearing, relegates the most salient inquiry to possible — but not certain — resolution on a § 2255 habeas petition.

At bottom, the majority offends logic with a basic “chicken and egg” scenario: It relies on a waiver whose validity is contingent upon the answer to a legal question to preclude the consideration of that very legal question.

Not surprisingly, given the convoluted nature of its reasoning, the majority’s ap-proaeh cannot be reconciled with our precedents. This circuit has dealt with ineffective assistance of counsel issues on appeal in connection with knowing and voluntariness challenges to plea agreements. I therefore respectfully dissent.

I

Before proceeding to the issues regarding Jeronimo’s ineffective assistance claim against his counsel, the majority begins by evaluating the Rule 11 colloquy. Without citing a single authority,2 the majority indicates that the colloquy “on its face ... shows that Jeronimo’s plea was knowingly and voluntarily made.” Ante at 1154.

Jeronimo stated under oath, however, that he did not understand the plea agreement because he was never informed of the fact that he qualified as a career criminal. He also testified that his counsel knew of his prior convictions, and that “I signed for 87 months.” If one believes those representations, and the district court did not state that it disbelieved them, then Jeronimo did not understand the agreement when he talked to his attorney Kolego, or when he began the Rule 11 colloquy with the district court judge, or during the Rule 11 colloquy when the judge asked him if he had discussed the sentencing guidelines with his attorney, or when the government mentioned that this prior conviction could affect his sentence, or after the Rule 11 colloquy. For, as far as the record shows, no one — -not Kolego, not the district court judge, not the prosecutor — ever mentioned that it was manda *1160 tory that the career offender provision of the law applied to Jeronimo, and that the minimum sentence he could receive was therefore 151 months.3 Mentioning the maximum statutory sentence did not take care of the problem, nor did informing Jeronimo that his sentence was ultimately up to the judge. The problem was that his lawyer had erroneously informed him that an 87 month sentence was at least a possibility (leaving aside any prediction or “deal” regarding that sentence), when it was not. So Jeronimo had erroneous information, precluding him from accurately evaluating his options and risks. In other words, his decision to plead guilty was not “knowing,” even if it appeared otherwise to the judge who took the plea.

Importantly, the problem here was not just a failure to make an accurate prediction or other assessment of the possibilities. It was an absolute certainty that, under the sentencing guidelines, Jeronimo would qualify as a “career criminal” if he pled guilty. See U.S.S.G. § 4B1.1 (2002); supra note 3.

Furthermore, the lawyer had the prior conviction information necessary to so inform Jeronimo.4 This case therefore concerns a defendant whose counsel left him uninformed about his certain legal fate if he accepted a plea agreement, and instead affirmatively indicated that a lower sentence was possible than was actually the case.

II

Given this predicament, one can easily understand why Jeronimo claimed in the district court, as the basis for his motion to withdraw his guilty plea, that the advice of his counsel was ineffective. The majority’s ultimate reason for refusing to hear that claim is that we generally do not hear ineffective assistance claims on direct appeal. The reason for that policy, however, is that normally, the record on appeal is deficient, as there was no litigation on effectiveness of counsel in the district court. In this case, however, the ineffectiveness issue and the merits question, *1161withdrawal of the guilty plea, collapse into one another and turn on identical facts. Consequently, there was a hearing on the ineffectiveness issue, where Jeronimo presented sworn testimony. To suggest that there is no record on the issue is therefore just plain wrong.

During the August 18, 2003, hearing concerning the motion to withdraw Jeroni-mo’s guilty plea, Jeronimo testified under oath. This is what he said:

QUESTION: And did you discuss the merits of the plea offer many times with your attorney?

ANSWER: Yes, a number of times.

QUESTION: And, finally, he convinced you that you should accept the plea offer; is that correct?

ANSWER: Yes.

QUESTION: And during your discussions with your attorney, did — do you know if he was aware of your prior criminal history?

ANSWER: Yes, he did know.

QUESTION: He knew that you had a prior felony conviction for drug distribution?

ANSWER: Excuse me, I’m sorry?

QUESTION: Your attorney knew that you had a prior conviction for drug distribution?

ANSWER: Yes.

QUESTION: Your attorney knew of that?

ANSWER: Yes, he knew that.

QUESTION: And he also knew, based upon your discussions with him, that had you [sic] a prior felony assault conviction; is that correct?

ANSWER: Yes.

QUESTION: In your many discussions with your attorney, did he predict — did you discuss the sentencing guidelines?

ANSWER: Yes, we did.

QUESTION: And did he predict what your sentence would be if you accepted the plea offer?

ANSWER: Yes.

QUESTION: And what was your understanding of the sentence you would receive based upon the plea offer?

ANSWER: Eighty-seven months.

QUESTION: During the conversations with your attorney, did the phrase “career offender” ever come up?

ANSWER: No, he didn’t tell me anything about that.

QUESTION: If you had known that you would receive a sentence of 151 months, would you have accepted the plea offer?

ANSWER: No, I would not have.

QUESTION: And all your lawyers have told you when it comes to sentencing that that would be left up to the judge, correct?

ANSWER: Yes. But I made a deal with my attorney, I trusted in him, I trusted in him, sir, and I signed for 87 months. When I realized that the sentence was longer, if I had realized, if I known [sic] that, I wouldn’t have sign [sic] it.

QUESTION: In fact, in this particular case, Judge Hogan, the judge you are in front of today, made that clear to you during the course of the plea petition, that it was going to be up to him what sentence you were going to get, correct?

ANSWER: Yes, that’s fine what you say, but what happened to the deal that I made with my attorney?

QUESTION: The deal that you made with your lawyer, sir, did not include what this judge was going to sentence you to, correct?

ANSWER: Yes.

*1162QUESTION: And, in fact, when the court asked you, this judge here, asked you is your guilty plea freely and voluntarily made, with a good understanding of the nature of the charges against you, and the matters in this guilty plea petition and plea bargain letter, and those things we’ve talked about today, you answered yes through an interpreter, did you not?

ANSWER: Because I made a deal with my attorney. I had spoken to him.

QUESTION: And then when the judge said [“]I’ll accept the guilty plea,[”] I told you something. And what I said was, “Please the court, before accepting the plea, I want to make sure that the defendant” — that would be you, sir — • “understands that under the relevant facts that the government is going to bring to the court’s attention and to probation’s attention is the fact the government will contend he has a prior delivery of a controlled substance conviction in 1994; and a felony assault in the second degree, two counts in 1995; that he was an illegal alien at the time of these drug trafficking crimes, as well as escapee and a fugitive from the Oregon Department of Corrections.”

I just want those relevant facts to be included in this colloquy so that Mr. Jeronimo is aware that that’s something the government may bring up, in fact, will bring up at sentencing before entering voluntarily his guilty plea.”

Do you remember me telling you that?

ANSWER: Yes, sir, I do.

QUESTION: And the court went further, this judge said, and do you understand that if the party (sic) agrees with those facts, it will likely affect the extent of your sentence?

ANSWER: I had talked about that vrith my attorney.

QUESTION: So when you pled guilty, you understood that you could face a maximum sentence of more than 151 months, did you not?

ANSWER: He never talked about — my attorney never talked about that. If I had known that, I would not have plead guilty.

QUESTION: Didn’t the court tell you, “the plea petition says the maximum sentence is 20 years imprisonment”? You heard that, didn’t you?

ANSWER: Yes.

QUESTION: You still pled guilty, right?

ANSWER: Because I had spoken to my attorney, I made a deal.

The government presented no testimony controverting Jeronimo’s sworn testimony. Nor did the judge decide whether the attorney did fail to provide Jeronimo with essential information.

The majority ignores Jeronimo’s sworn testimony. It cannot be the case that because the testimony was uncontroverted, an appellate court, in the absence of any district court credibility determination, can simply assume the opposite is true. Thus, although the majority suggests that Jeron-imo cannot make out an ineffective assistance claim because “the record contains no evidence from Kolego,” ante at 1156, this suggestion is without any basis. The government could have put on such evidence but did not. Jeronimo was not required to, once he told the court his version of events.

Moreover, on the merits of the ineffective assistance claim, a failure to inform one’s client of the mandatory application of a sentencing provision can never qualify as a “strategic, decision.” We are not evaluating this attorney’s decisions in front of a judge or jury. Instead, we are considering *1163only whether the attorney deficiently advised his client, so that his client’s plea was not knowing and voluntary. See, e.g., Chizen v. Hunter, 809 F.2d 560 (9th Cir.1986); Iaea v. Sunn, 800 F.2d 861 (9th Cir.1986).

The very reason for a Rule 11 plea colloquy is to ensure that “the criminal defendant who pleads guilty understands exactly what that plea means.” United States v. Rios-Ortiz, 830 F.2d 1067, 1070 (9th Cir.1987). As this court recognized in Iaea, “ ‘an intelligent assessment of the relative advantages of pleading guilty is frequently impossible without the assistance of an attorney.’ ” 800 F.2d at 865 (quoting Brady v. United States, 397 U.S. 742, 748 n. 6, 90 S.Ct. 1463, 25 L.Ed.2d 747 (1970)). The majority’s suggestion that an attorney has strategic discretion in advising his client of the consequences of a guilty plea disregards the fundamental tenet that “counsel [has] a duty to supply criminal defendants with necessary and accurate information.” Id. How can the failure to fulfill a fundamental duty — a failure that results in a significantly longer prison sentence than his client would have agreed or pled to — possibly qualify as counsel’s strategic decision?

I conclude that, if Jeronimo’s testimony is credited, the record supports his contention that Jeronimo’s guilty plea was not knowing and voluntary, because he was misinformed by his counsel regarding the sentencing options.5

Ill

The majority thus stumbles most fundamentally when it suggests that we cannot review this challenge to Jeronimo’s appeal waiver.

This case is not like most ineffectiveness challenges. In most cases, such a challenge is not made until appeal, so there is no record in the court of conviction concerning the issue. Here, Jeronimo raised the very same knowing and voluntary waiver issue in the district court as the basis for his contention that he should be allowed to withdraw his plea. The district court had a hearing on the issue, at which it took Jeronimo’s sworn testimony on this issue. The government had notice of the ineffective assistance issue in the Motion to Withdraw Plea of Guilty Due to Inadequate and Fraudulent Representation By Legal Counsel, but did not put on any opposing testimony.

In these special circumstances — where the ineffective assistance issue was properly raised and litigated in the district court — this court does have the evidence necessary to determine whether Jeroni-mo’s plea was “knowingly and voluntarily” made. See United States v. Laughlin, 933 F.2d 786, 788-89 (9th Cir.1991) (explaining that the reason habeas is often a preferable posture for ineffectiveness challenges is to establish “ ‘what counsel did, why it was done, and what, if any, prejudice resulted’ ” (quoting United States v. Pope, 841 F.2d 954, 958 (9th Cir.1988))). Based on Jeronimo’s sworn testimony, we know what counsel did — he failed to advise Jer-onimo that the he would be sentenced as a “career criminal,” and instead informed him erroneously that a lesser sentence was possible. For the reasons discussed supra, we know that Kolego had a duty to *1164provide this information. It was not in Kolego’s strategic discretion to erroneously inform Jeronimo in this manner. Finally, we know what prejudice resulted — Jer-onimo agreed to a plea that, as he testified under oath, .he would not have accepted had he .known of the “career criminal” provision. As no strategic discretion could justify Kolego’s actions, “it is not necessary to expand the record because in determining reasonableness we need go no further than ruling” that such a failure to advise is contrary to law. United States v. Anderson, 850 F.2d 563, 565 n. 1 (9th Cir.1988). Given that there was a hearing in the lower court regarding this issue in which Jeronimo was questioned and testified, this court can and should address Jeronimo’s challenge.6

Notwithstanding the majority’s assertion to the contrary, the Ninth Circuit has considered and decided the question of ineffective assistance of counsel pursuant to a challenge to a plea. See Signori, 844 F.2d at 638-39 (reviewing a challenge to a plea on direct appeal based on ineffective assistance of counsel); cf. Chizen, 809 F.2d at 562 (reviewing a challenge to a plea on direct appeal based on claim of “counsel’s misrepresentations as to what his sentence in fact would be”). The majority’s argument that we cannot consider an ineffective assistance claim is inconsistent with Signori, which reviewed the incompetency challenge directly rather then dismissing the plea challenge to await a § 2255 motion.7

While asserting that this court does not review ineffective assistance claims on direct appeal, the majority fails to cite any case refusing to consider an ineffectiveness issue on direct appeal in which the issue was litigated in district court on a plea withdrawal motion (or for any other reason, for that matter). Every case the majority cites for its central proposition concerns an ineffectiveness claim involving attorney conduct unrelated to any plea withdrawal hearing, or to any other hearing held before the district court. The cases cited thus offer little enlightenment regarding an ineffective assistance claim presented at an evidentiary hearing as part of an effort to withdraw a guilty plea. See United States v. Daychild, 357 F.3d 1082, 1094-95 (9th Cir.2004) (attorney filed pretrial motions to continue when client wanted a speedy trial); United States v. McKenna, 327 F.3d 830, 845 (9th Cir.) (failure to admit evidence at trial and failure to file motions), cert. denied, 540 U.S. 941, 124 S.Ct. 359, 157 L.Ed.2d 254 (2003); Laughlin, 933 F.2d at 788-89 (attorney conduct during a hearing for revocation of probation); Anderson, 850 F.2d at 565 n. 1 (failure to request a particular jury instruction); United States v. Birges, 723 F.2d 666, 669-70 (9th Cir.1984) (failure to request witnesses). Given the unique connection in this case between the ineffec*1165tiveness issue and the merits question on appeal, the majority’s reliance on the court’s general reluctance to address ineffectiveness claims on direct appeal is entirely out of place.

IV

In sum: The majority refuses to consider the appeal of a criminal defendant who, in sworn and uneontradicted testimony, made clear that, due to his attorney’s representations, he never understood the mandatory legal consequences of his plea agreement. By purporting to enforce the appeal waiver, the majority refuses to reach an ineffectiveness of counsel claim that could resolve both the availability of an appeal and the merits of the appeal, and that was litigated below. Its refusal is based on cases in which, unlike here, the district court had no occasion to hold a hearing on the ineffectiveness claim the defendant wishes to raise on appeal. Those cases have no application here. The majority’s insistence on enforcing this so-called meeting of the minds strips Jeroni-mo of the chance to assert many of the basic rights afforded criminal defendants in our adversarial system.8

I respectfully dissent.