Misunderstanding Sentencing Exposure Is Not a “Fair and Just Reason” to Withdraw a Guilty Plea: Commentary on United States v. Carale Shields

I. Introduction

This commentary examines the Sixth Circuit’s unpublished, per curiam decision in United States v. Carale Shields, No. 25-5106 (6th Cir. Dec. 8, 2025), affirming the denial of a defendant’s attempt to withdraw a guilty plea in a federal methamphetamine case. The opinion reinforces several recurring principles in federal criminal practice: 1. A guilty plea will be upheld as valid where the Rule 11 colloquy is thorough and the record demonstrates a knowing, voluntary, and intelligent plea, even if the defendant later claims confusion about sentencing consequences. 2. Misunderstanding (or claiming to misunderstand) one’s Guidelines range, career-offender status, or the court’s acceptance of the plea agreement does not, without more, constitute a “fair and just reason” to withdraw a plea under Federal Rule of Criminal Procedure 11(d)(2)(B). 3. A defendant’s prior exposure to the criminal justice system, previous presentence investigation, and failure to promptly move for withdrawal weigh heavily against post-plea efforts to undo a conviction. The case centers on defendant-appellant Carale Shields, who was charged in a multi-defendant methamphetamine conspiracy, entered into two separate Rule 11(c)(1)(C) plea agreements, and later sought to withdraw his second guilty plea by asserting confusion about his plea, the sentencing guidelines, and his career-offender designation. The Sixth Circuit rejected these claims and affirmed the district court. Although “not recommended for publication” and thus not binding precedent in the Sixth Circuit, the decision is a useful restatement and application of settled law on the validity of guilty pleas and the standards governing plea withdrawal. ---

II. Factual and Procedural Background

A. Indictment and Charges

In 2019, a federal grand jury in the Western District of Tennessee indicted Shields and ten co-defendants for their roles in a methamphetamine conspiracy. A superseding indictment charged Shields with: 1. Count 1 – Conspiracy to distribute and possess with intent to distribute methamphetamine, in violation of 21 U.S.C. §§ 841(a)(1), 846. 2. Count 2 – Aiding and abetting distribution and possession with intent to distribute methamphetamine, in violation of 18 U.S.C. § 2 and 21 U.S.C. § 841(a)(1). 3. Count 11 – Being a felon in possession of ammunition, in violation of 18 U.S.C. §§ 922(g)(1), 924(a)(2). These charges exposed Shields to substantial prison time, especially in light of his extensive criminal history.

B. The First Plea Agreement and Presentence Investigation

Shortly before trial, Shields requested a change-of-plea hearing and entered into his first plea agreement with the government: - He agreed to plead guilty to Count 2. - The government agreed to dismiss Counts 1 and 11. - The parties stipulated to a 120-month sentence under Rule 11(c)(1)(C). The district court accepted the guilty plea (i.e., the admission of guilt) and ordered a presentence investigation. The probation office prepared a draft Presentence Report (PSR), which: - Attributed to Shields responsibility for 5,443.2 grams of methamphetamine. - Classified him as a career offender under USSG § 4B1.1 based on five prior drug convictions, including two for offenses committed while he was a juvenile. - Reflected a much higher Guidelines range than the 120-month stipulated sentence. Shields objected to the drug type and quantity but did not object to the PSR’s determination that he was a career offender. At sentencing, the district court rejected the 11(c)(1)(C) plea agreement (i.e., declined to be bound to 120 months) and set the case for trial. The plea of guilt itself was not at issue; the rejection was of the sentencing agreement.

C. The Second Plea Agreement (Day of Trial)

On the day set for trial, Shields again chose to plead guilty to Count 2. This time, the parties negotiated a new Rule 11(c)(1)(C) plea agreement, providing: - Shields would plead guilty to Count 2. - The government would dismiss the remaining counts. - The agreed sentence would be 165 months’ imprisonment. - Critically, the agreement stated:

"The parties believe that the defendant is a Career Offender pursuant to USSG § 4B1.1. If the defendant is not a Career Offender th[e]n both parties may withdraw from the plea agreement."

At the change-of-plea hearing: - The district court conducted a Rule 11 colloquy. - It reviewed the terms of the plea agreement with Shields, including the career-offender clause. - It examined the factual basis (including evidence that Shields sold methamphetamine in 2017 on at least three occasions). - It specifically found Shields competent, and his plea knowing and voluntary. - It then expressly stated: "So, Mr. Shields, I'm going to accept your plea of guilty to Count 2 of [the] superseding indictment." That same day, the court entered a written order documenting acceptance of the plea.

D. Motions to Withdraw the Guilty Plea

First motion: Nine weeks after the second plea, Shields moved to withdraw his guilty plea and requested new counsel. He claimed confusion and dissatisfaction with his representation. On his scheduled sentencing date, the district court: - Allowed prior counsel to withdraw. - Denied the motion to withdraw the guilty plea. - Continued sentencing. Renewed motion: Five months later, with new counsel, Shields renewed his motion. He contended: - He thought the plea had not yet been finally accepted. - He believed he could withdraw because he thought he was not a career offender, invoking the plea’s conditional language. - He misunderstood the factual basis, the Guidelines calculation, and the PSR process. - His confusion may have been influenced by an old diagnosis of adjustment disorder. The district court found no “fair and just reason” to permit withdrawal under Rule 11(d)(2)(B) and again denied the motion.

E. Sentencing and Appeal

At sentencing, the district court: - Found Shields to be a career offender under USSG § 4B1.1. - Calculated a Guidelines range of 188–235 months (total offense level 31; criminal history category VI). - After considering 18 U.S.C. § 3553(a) factors, accepted the 165-month Rule 11(c)(1)(C) agreement. - Imposed 165 months’ imprisonment and three years of supervised release. On appeal, Shields raised two arguments: 1. His guilty plea was involuntary and not knowing, given his asserted misunderstandings. 2. The district court abused its discretion in denying his motions to withdraw his plea. The Sixth Circuit affirmed. ---

III. Summary of the Sixth Circuit’s Decision

The Sixth Circuit’s holdings can be summarized as follows: 1. Validity of guilty plea: Under de novo review, the court held that Shields’s plea was valid—voluntary, knowing, and intelligent—viewed under the totality of the circumstances. The Rule 11 colloquy complied with procedural requirements, and the record showed Shields knew the nature of the charge, his potential sentencing exposure, and the meaning of the career-offender provision. 2. Denial of plea-withdrawal motion: Applying an abuse-of-discretion standard, and the multi-factor test from United States v. Bashara, the court concluded Shields failed to show a “fair and just reason” to withdraw his plea. The lengthy delay, his lack of a credible explanation for it, his failure to maintain innocence, his extensive criminal history, and his prior exposure to the PSR and career-offender finding supported the district court’s decision. Because he failed at this threshold, the court held that it was unnecessary to reach the prejudice-to-the-government factor. The case therefore reinforces the strong presumption that a guilty plea is final once it is properly taken and accepted, and that tactical regret or belated dissatisfaction with the perceived consequences does not suffice for withdrawal. ---

IV. Precedents and Authorities Applied

The opinion stands firmly on established Sixth Circuit and Supreme Court precedent. Key citations and their relevance include:

A. Validity of Guilty Pleas

1. Brady v. United States, 397 U.S. 742 (1970) - Brady is the foundational case on the constitutional validity of guilty pleas. It holds that a plea is valid if it is “voluntary” and “intelligent” with “sufficient awareness of the relevant circumstances and likely consequences.” - The Shields court quoted Brady, emphasizing that the defendant must have a “sufficient awareness of the relevant circumstances and likely consequences” of his plea. This standard frames both the inquiry into voluntariness and Shields’s alleged confusion about the Guidelines and career-offender status. 2. United States v. Dixon, 479 F.3d 431 (6th Cir. 2007) - Cited for the propositions that: - The validity of a guilty plea is reviewed de novo. - Rule 11(d)(2)’s purpose is to prevent tactical, post hoc plea withdrawals. - Dixon also contains the frequently cited language (originally from Alexander) that Rule 11 is designed to undo “a hastily entered plea made with unsure heart and confused mind,” not to permit regret-driven strategic reversals. 3. United States v. Hockenberry, 730 F.3d 645 (6th Cir. 2013) - The court quotes Hockenberry for the totality-of-the-circumstances test in evaluating plea validity. - It also later relies on Hockenberry for the principle that if no “fair and just reason” is shown under Rule 11(d)(2)(B), courts need not reach the question of prejudice to the government. 4. United States v. Young Ko, 485 F. App’x 102 (6th Cir. 2012) (per curiam) - Cited for the articulation of the totality-of-the-circumstances framework in assessing whether the plea was knowing, voluntary, and intelligent. These authorities collectively reaffirm that a properly conducted Rule 11 colloquy creates a strong presumption that the plea is valid.

B. Withdrawal of Guilty Pleas and Rule 11(d)(2)(B)

1. Federal Rule of Criminal Procedure 11(d) - Rule 11(d)(1): Before the court accepts a plea, a defendant may withdraw it “for any reason or no reason.” - Rule 11(d)(2)(B): After acceptance but before sentencing, withdrawal is permitted only if the defendant shows a “fair and just reason.” - Shields tried to place himself in the Rule 11(d)(1) world by claiming his plea had not been accepted, but the record (oral and written) flatly contradicted him. 2. United States v. Catchings, 708 F.3d 710 (6th Cir. 2013) - Cited for the standard of review—denial of a motion to withdraw a guilty plea is reviewed for abuse of discretion. - Also cited for the seven non-exclusive factors used to assess “fair and just reason,” originally set out in Bashara. 3. United States v. Bashara, 27 F.3d 1174 (6th Cir. 1994) - Provides the now-canonical list of factors courts use in evaluating whether a defendant has presented a “fair and just reason”: 1. Time between plea and motion. 2. Reason for not moving earlier. 3. Assertion or maintenance of innocence. 4. Circumstances of the plea. 5. Defendant’s nature and background. 6. Prior experience with the criminal justice system. 7. Prejudice to the government. - Shields’s motion fails under these factors, which the opinion applies carefully. 4. United States v. Alexander, 948 F.2d 1002 (6th Cir. 1991) - Quoted indirectly through Dixon for the notion that Rule 11 permits withdrawal of “hastily entered” pleas made with confused minds, but not tactical reversals after reflection. 5. United States v. Benton, 639 F.3d 723 (6th Cir. 2011) and United States v. Baez, 87 F.3d 805 (6th Cir. 1996) - Cited to show that delays even as short as one month (Benton) or 67 days (Baez) between plea and motion to withdraw have been held too long to favor withdrawal. - Here, Shields waited nine weeks (about 63 days) before filing his first motion, which weighed against him. 6. United States v. Martin, 668 F.3d 787 (6th Cir. 2012) - Used for two propositions: - Lack of communication with counsel alone is not a sufficient reason to justify delay in moving to withdraw. - Statements of guilt under oath support denial of a motion to withdraw and are not easily overcome by later assertions. 7. United States v. Ellis, 470 F.3d 275 (6th Cir. 2006) and United States v. Morrison, 967 F.2d 264 (8th Cir. 1992) (quoted in Ellis) - Reinforce that once a defendant has entered a knowing and voluntary guilty plea at a hearing where he admits the crime, the opportunity to withdraw “should seldom arise.” 8. United States v. Haygood, 549 F.3d 1049 (6th Cir. 2008) and United States v. Spikes, 158 F.3d 913 (6th Cir. 1998) - Cited for the abuse-of-discretion standard: a district court abuses its discretion if it relies on clearly erroneous facts or misapplies the law. 9. United States v. Lewis, 800 F. App’x 353 (6th Cir. 2020) - Used to reject Shields’s argument that his lack of prior federal (as opposed to state) experience weighed in favor of withdrawal. The court reiterates that extensive state criminal history counts heavily as prior experience with the criminal justice system. Together, these cases give structure to the court’s application of Rule 11(d)(2)(B) and frame why Shields’s motion was deemed tactical and unsupported. ---

V. The Court’s Legal Reasoning

A. Validity of the Guilty Plea

The Sixth Circuit reviewed the plea’s validity de novo, asking whether Shields’s plea was knowing, voluntary, and intelligent under Brady and its progeny. 1. Alleged confusion about whether the court had accepted the plea Shields argued he believed his plea had not been finally accepted due to the district court’s discussion of possible acceptance or rejection of the Rule 11(c)(1)(C) agreement. The appellate court pointed to two decisive facts: - At the close of the second plea hearing, the court explicitly stated: “So, Mr. Shields, I'm going to accept your plea of guilty to Count 2 of [the] superseding indictment.” - The same day, the court entered a written order confirming acceptance. Under Rule 11, acceptance of the plea itself (the admission of guilt) is distinct from later acceptance or rejection of the sentence agreement. However, here the district judge made it unmistakably clear that the guilty plea had been accepted. Shields’s subjective, contrary belief was unsupported by the record. 2. Alleged confusion about the factual basis Shields claimed he was confused about “exactly what conduct” he was admitting. But at the plea hearing: - The court and parties reviewed a stipulated factual basis describing methamphetamine sales in 2017. - The factual basis included an individual’s statement to the FBI that he obtained methamphetamine from Shields on at least three occasions. - Shields affirmed the accuracy of this factual basis. Given these on-the-record admissions, the court found no factual confusion undermining the plea. 3. Alleged confusion about the Guidelines, drug quantity, and career-offender status Shields asserted he believed his Guidelines range would be based solely on the 42.57 grams of methamphetamine he sold to a particular individual and that he did not understand his career-offender designation. The court rejected this for several reasons: - No drug-quantity limitation in the plea agreement. The plea did not promise that sentencing would be based only on 42.57 grams. Shields’s belief contradicted the document he signed. - Prior PSR experience. After his first plea, a draft PSR had already: - Attributed 5,443.2 grams of methamphetamine to him. - Classified him as a career offender under USSG § 4B1.1 based on five prior drug convictions (including two for offenses committed as a juvenile). - Failure to object to career-offender status. Shields had objected to drug type and quantity in the PSR but did not object to the career-offender designation at that time, undermining his later claim of confusion. - Plea colloquy confirmation. At the second plea hearing: - The district court confirmed Shields was familiar with the Guidelines and aware that a PSR had already been prepared. - The court specifically walked through the plea provision stating that “the parties believe” he is a career offender. - Shields said he understood this term. On these facts, the court concluded that any claimed misunderstanding about the Guidelines or career-offender status was contradicted by the record and insufficient to invalidate the plea. 4. Alleged dissatisfaction with counsel Shields pointed to his statement at the plea hearing that he was “not fully satisfied” with his lawyer. - The district court immediately probed the concern, allowed discussion, and addressed his complaints. - After this discussion, Shields stated he was “ready to proceed” and “willing to accept the plea agreement.” The appellate court treated this as a typical mid-hearing concern that was adequately resolved on the record. It did not rise to the level of ineffective assistance or coercion sufficient to affect voluntariness. 5. Conclusion on plea validity Weighing the totality of the circumstances—prior PSR, clear explanation of the agreement, explicit acceptance of the plea, confirmation of understanding, and resolution of concerns about counsel—the Sixth Circuit held the plea was knowing, voluntary, and intelligent.

B. Denial of Motion to Withdraw the Guilty Plea

The denial was reviewed for abuse of discretion, meaning the appellate court would reverse only if the district court relied on clearly erroneous facts or misapplied the law. The court applied the Bashara/Catchings factors: 1. Length of delay between plea and motion - Shields waited nine weeks after the second plea to file his first withdrawal motion. - The Sixth Circuit has upheld denial of withdrawal where the delay was: - As short as one month (Benton). - 67 days (Baez). - Here, a roughly 63-day delay counted strongly against him. 2. Reason for failing to move earlier Shields initially claimed he had contacted his lawyer’s office “several weeks” earlier and that counsel had only recently discussed withdrawal with him. The Sixth Circuit held that: - Even assuming some delay was attributable to counsel, Shields still waited several weeks before raising the issue, and - Under Martin, lack of communication with counsel is not enough to excuse such delay. In his renewed motion, Shields argued: - He did not think “time was of the essence,” because: - He believed the court had not accepted the plea (thus he thought he could withdraw “for any reason or no reason” under Rule 11(d)(1)). - He believed he was not a career offender and therefore could withdraw under the plea’s clause allowing either party to withdraw if he did not qualify as such. The court rejected both: - Acceptance of plea: The record disproved his belief; the court had clearly accepted the plea and documented it in an order. - Career-offender clause: The agreement said only that the parties believed he was a career offender; it did not entitle him to withdraw simply because he later asserted he was not one. Moreover: - The PSR and plea agreement indicated career-offender status. - Shields had been put on notice and had raised no objection earlier. Thus, his proffered reasons for delay were factually and legally weak. 3. Assertion or maintenance of innocence - Shields never claimed he was innocent of the underlying conduct. - He pleaded guilty twice to Count 2. - Under Martin and Ellis, sworn admissions of guilt at a plea hearing strongly support denial of a motion to withdraw. - His later dissatisfaction centered on sentencing expectations, not innocence. This factor weighed heavily against him. 4. Circumstances underlying the entry of the plea Shields reiterated his arguments about misunderstanding the factual basis, the Guidelines, and the acceptance of the plea. The court: - Referred back to its plea-validity analysis. - Noted that the district court had conducted a meticulous Rule 11 colloquy, confirmed understanding of rights, charges, consequences, and the plea terms. - Pointed out that Shields’s concerns with counsel were addressed on the record, after which he voluntarily proceeded. The Sixth Circuit found no coercion, confusion, or irregularity in those circumstances that would support withdrawal. 5. Defendant’s nature and background - Shields claimed an “untreated diagnosis of adjustment disorder” might explain his confusion. - But he also told the district court: - He was 44 years old. - He had obtained his GED. - He had undergone psychological evaluation almost 30 years earlier as a juvenile, with no ongoing treatment or diagnosed impairment. - The district court found—and the appellate court accepted—that he understood he was pleading guilty and comprehended the consequences. This factor did not favor withdrawal. 6. Prior experience with the criminal justice system - Shields had no prior federal convictions, but extensive state history: - Criminal involvement from age 13. - Over two dozen juvenile adjudications and adult convictions. - Citing Lewis, the court held that extensive state experience counts as significant prior experience with the criminal justice system and does not help a defendant seeking plea withdrawal. Far from being a novice, Shields was a seasoned defendant who understood criminal proceedings. 7. Prejudice to the government - The district court did not analyze government prejudice. - Under Hockenberry, this omission is acceptable because prejudice is reached only if the defendant first establishes a “fair and just reason.” - Having failed on the first six factors, Shields never passed that threshold. Overall, the Sixth Circuit agreed that “the balance of the Bashara factors strongly weighed” against withdrawal, and that Shields’s decision to plead guilty on the day of trial was a tactical choice—precisely the sort of calculated maneuver Rule 11(d)(2)(B) does not protect. ---

VI. Complex Legal Concepts and Terminology Explained

This case engages several procedural and sentencing concepts that can be opaque. The following explanations are designed for clarity.

A. Rule 11(c)(1)(C) Plea Agreements

Under Federal Rule of Criminal Procedure 11(c), the government and a defendant may enter into different types of plea agreements: - 11(c)(1)(B) agreements: Government makes a recommendation or request regarding sentence, but the court is not bound by it. - 11(c)(1)(C) agreements: The parties agree on a specific sentence (or sentencing range or calculation). If the court accepts the agreement, it is legally bound to impose that sentence (or within that agreed framework). In Shields’s case: - Both plea agreements were under Rule 11(c)(1)(C). - The first proposed 120 months; the second, 165 months. - The district court was free to accept the plea of guilty but later reject the sentencing agreement, which it did with the first plea agreement. - With the second agreement, the court eventually accepted the 165-month sentence at final sentencing.

B. Acceptance of a Plea vs. Acceptance of a Plea Agreement

These are conceptually distinct: - Acceptance of the guilty plea: The court determines that the plea is knowing, voluntary, intelligent, supported by an adequate factual basis, and complies with Rule 11. - Acceptance of the plea agreement (especially 11(c)(1)(C)): The court decides whether to be bound by the agreed-upon sentencing terms. Under Rule 11(d): - Before the court accepts the plea, the defendant can withdraw without cause (Rule 11(d)(1)). - After the court accepts the plea (even if it has not yet accepted the sentencing agreement), the defendant must show a “fair and just reason” (Rule 11(d)(2)(B)). Shields’s misunderstanding (or claimed misunderstanding) conflated these concepts. He incorrectly believed his plea was unaccepted and therefore revocable at will, despite clear statements and a court order to the contrary.

C. “Career Offender” Under USSG § 4B1.1

The “career offender” provision of the U.S. Sentencing Guidelines dramatically increases a defendant’s offense level and criminal history category if certain criteria are met, typically including: 1. The defendant was at least 18 at the time of the instant offense. 2. The instant offense is a felony that is either a “crime of violence” or a “controlled substance offense.” 3. The defendant has at least two prior felony convictions of either a crime of violence or a controlled substance offense. When a defendant qualifies: - His offense level and criminal history category are adjusted upward. - This often results in a much higher advisory Guidelines range. In Shields’s case: - The PSR determined that he had multiple prior drug convictions qualifying as “controlled substance offenses,” including two based on conduct committed as a juvenile (likely prosecuted as adult-qualifying offenses or otherwise meeting Guidelines counting rules). - His career-offender status produced a Guidelines range of 188–235 months; the 165-month agreement was a downward deviation from that advisory range. The plea agreement’s clause—that both parties “believe” he is a career offender and “may” withdraw the agreement if he is not—was a conditional term about the agreement’s continued validity. It did not entitle Shields to withdraw at will simply because he later claimed to disagree with the classification.

D. Presentence Investigation and Report (PSR)

The PSR is prepared by the U.S. Probation Office after a defendant is found guilty (by plea or verdict). It typically includes: - The offense conduct. - The defendant’s criminal history. - Guideline calculations (offense level, criminal history category, and range). - Information on personal background, mental health, and other factors relevant under 18 U.S.C. § 3553(a). The defendant and counsel: - Receive the PSR. - May file written objections to factual findings or Guideline calculations. - May argue those objections at sentencing. Shields had already gone through this process after his first plea. He had actual notice of the government’s and probation office’s views on drug quantity and career-offender status. His failure to object to the career-offender classification at that earlier stage undercut his later claims of confusion.

E. “Fair and Just Reason” Under Rule 11(d)(2)(B)

After a plea is accepted, the defendant must show a “fair and just reason” to withdraw it. This is not a low bar; it is more demanding than the pre-acceptance standard. The Bashara factors guide courts in assessing whether this standard is met. Key points: - Tactical regret or “buyer’s remorse” is not a fair and just reason. - Late realization that the sentence may be harsher than hoped is generally insufficient, especially where the court warned the defendant and the plea agreement did not guarantee a particular Guidelines outcome beyond the stipulated (C) sentence. - A hasty plea entered under confusion or misunderstanding may suffice, but the defendant must produce more than bare assertions—he must show that confusion was objectively reasonable and not contradicted by the record. In Shields, the court viewed his motion as a classic example of tactical reconsideration after seeing how his Guidelines and sentencing exposure looked in practice.

F. Standards of Review: De Novo vs. Abuse of Discretion

The court applied two distinct standards: - De novo review (no deference) for the legal validity of the guilty plea. - Abuse-of-discretion review for the denial of the motion to withdraw. Abuse-of-discretion is highly deferential; appellate courts will not reverse unless the district court: - Relies on clearly erroneous facts, or - Applies an incorrect legal standard. Here, the district court’s factual findings about Shields’s understanding, mental state, and tactical motives were supported by the record, and the correct legal standards (Brady, Rule 11, Bashara factors) were applied. ---

VII. Impact and Significance

Although United States v. Carale Shields is unpublished and non-precedential, it carries several practical implications for plea practice in the Sixth Circuit and beyond.

A. Reinforcing the Finality of Guilty Pleas

The decision underscores the strong presumption of finality once a guilty plea has been: - Entered in compliance with Rule 11, and - Accepted by the court. Defendants cannot easily undo such pleas based on alleged subjective misunderstandings—especially where: - The plea colloquy was clear and comprehensive. - The defendant had actual prior exposure to the PSR and Guidelines issues. - The defendant has a long criminal history and is thus familiar with the system.

B. Misunderstanding Sentencing Consequences Is Usually Not Enough

The case reinforces a line of authority that: - A defendant’s inaccurate expectation about sentence length, drug quantity, or Guideline outcomes does not typically invalidate an otherwise valid plea. - This is particularly true when no express promise has been made in the plea agreement and the court has given standard warnings (e.g., that any Guideline estimate is not binding). In Shields’s situation, his belief that only 42.57 grams would matter, or that he was not a career offender, was contrary to the PSR, the plea language, and his colloquy statements. Those sorts of claims will ordinarily fail on appeal.

C. Career-Offender Clauses in Plea Agreements

The opinion provides practical guidance on plea agreements that contain career-offender contingencies: - Language such as “the parties believe the defendant is a career offender” paired with a mutual withdrawal option if he is not, is interpreted according to its plain meaning: - It does not imply that the defendant can claim non-career-offender status unilaterally to escape the plea. - It contemplates an objective determination that the Guidelines do not classify him as such (e.g., at sentencing), at which point either party may withdraw. Defense counsel should ensure that clients understand: - Distinctions between a belief and a guarantee. - That such clauses usually operate as a safety valve, not an open-ended right to change one’s mind.

D. Importance of the PSR and Prior Plea History

Shields had already: - Pleaded guilty once. - Received a PSR showing career-offender status and a much larger drug quantity. - Filed targeted objections (but not to career-offender status). This history made it very difficult to credibly assert later confusion. Going forward, this case suggests that: - Defendants who have gone through the PSR process will face an even steeper climb in arguing that they misunderstood key sentencing issues. - District courts and appellate courts will rely heavily on prior PSRs and objections—or lack thereof—when evaluating post-plea claims.

E. Strategic Timing and “Tactical” Pleas

The fact that Shields entered his second plea on the day of trial, then waited nine weeks to seek withdrawal, supported the view that: - The plea was a tactical choice to avoid trial risk. - The later motion was a tactical reconsideration following reassessment of sentencing exposure. The Sixth Circuit’s opinion reiterates that Rule 11 is not designed to facilitate such strategic second-guessing.

F. Lessons for Practitioners

1. For defense counsel: - Carefully explain: - The difference between the plea and the plea agreement. - The effect and operation of Rule 11(c)(1)(C). - Career-offender criteria and their massive impact on sentencing. - Create a record: - That the defendant understands these distinctions. - That any disputed issues (e.g., career-offender status) are recognized and reserved for argument at sentencing, not left in limbo. 2. For prosecutors: - Draft career-offender clauses with clarity, specifying: - How and when the determination will be made. - Who may withdraw and under what circumstances. - Be aware that including such clauses may later be invoked by defendants claiming misunderstanding; clear drafting and detailed plea colloquies can minimize that risk. 3. For district courts: - Continue to conduct meticulous Rule 11 colloquies. - Explicitly differentiate acceptance of the plea from acceptance of a (c)(1)(C) agreement, especially in complex or repeat-plea cases. - Address any expressions of dissatisfaction with counsel on the record, and verify the defendant’s readiness and willingness to proceed. ---

VIII. Conclusion: Key Takeaways

United States v. Carale Shields does not break new doctrinal ground, but it strongly reaffirms several core principles of federal plea law in the Sixth Circuit: 1. Rule 11 colloquies matter. A thorough on-the-record inquiry into voluntariness, understanding, and factual basis makes it extremely difficult for defendants to later overturn pleas. 2. “Fair and just reason” is a meaningful threshold. Time delay, absence of a credible explanation, failure to assert innocence, and prior criminal-justice experience all weigh heavily against withdrawal when, as here, the motion appears tactical. 3. Subjective misunderstandings—especially about sentencing—must yield to the objective record. Where the PSR, plea documents, and court statements all point one way, a defendant’s contrary assertion will rarely prevail. 4. Career-offender provisions in plea agreements are not escape hatches. They must be read in context, and claims of confusion about them must be measured against prior PSRs and colloquy admissions. In sum, the Sixth Circuit’s decision in Shields sends a clear message: once a properly conducted Rule 11 plea is entered and accepted, defendants cannot easily unwind it by post hoc claims of confusion about sentencing exposure or career-offender status, particularly where those issues were squarely presented before and during the plea process. The opinion thus contributes to the broader jurisprudence emphasizing the stability and finality of guilty pleas in the federal system.