United States v. Simpkins – Eleventh Circuit Clarifies that Courts Need Not Forecast Guideline Consequences When Accepting Waivers and Guilty Pleas

Introduction

United States v. Richard Simpkins (No. 23-10695, 11th Cir. July 3 2025) presented the Eleventh Circuit with questions about the validity of a defendant’s (1) waiver of indictment, (2) waiver of appeal, and (3) guilty plea to a superseding information charging conspiracy to commit money laundering. Richard Simpkins originally faced a three-count indictment for bank-fraud related offenses carrying up to 30 years’ imprisonment. The government later offered a superseding information with a single money-laundering-conspiracy count (maximum 20 years) in exchange for the defendant’s cooperation and waivers. Simpkins pleaded guilty, received a 48-month sentence, and then appealed, claiming that neither his waiver of indictment nor his guilty plea was knowing, intelligent, or voluntary because the court did not warn him that the Guidelines range associated with the new charge was allegedly higher than with the original indictment.

The Eleventh Circuit affirmed, crystallising an important procedural rule: when a district court accepts a waiver of indictment and a guilty plea, Rule 11 requires that the defendant be advised of the nature of the charge and the maximum statutory penalties, but the court is not required to predict or explain every possible sentencing-Guideline permutation, including increases that may arise from the substitution of a different statutory offense. That clarification, while consistent with prior circuit dicta, is now squarely endorsed in a published decision and will guide plea-colloquy practice within the Eleventh Circuit.

Summary of the Judgment

Standard of Review. Because Simpkins did not object below, the court reviewed for plain error.
Waiver of Indictment. The Rule 7(b) waiver executed in open court was valid; the district court properly advised Simpkins of his rights and obtained an on-the-record confirmation.
Waiver of Appeal. The sentencing-appeal waiver was enforceable; the magistrate judge articulated the waiver and its three limited exceptions.
Guilty Plea. The plea met Rule 11 requirements: no coercion, full awareness of the nature of the charge, and awareness of the statutory maximum penalties.
No Plain Error. The district court had no Rule 11 duty to speculate about future Guideline calculations or to compare hypothetical ranges tied to the original indictment.
Result. Conviction and 48-month sentence affirmed; ancillary arguments (Guideline disparity, ineffective assistance) deemed abandoned for insufficient briefing.

Analysis

A. Precedents Cited

The panel anchored its reasoning in a line of Eleventh Circuit cases governing plea procedures and appellate waivers:

United States v. Chubbuck, 252 F.3d 1300 (11th Cir. 2001): established plain-error framework for unobjected-to plea-colloquy defects.
United States v. Madden, 733 F.3d 1314 (11th Cir. 2013): articulated four-prong plain-error test; cited for standard.
United States v. Moore, 954 F.3d 1322 (11th Cir. 2020): confirmed validity requirements for Rule 7(b) indictment waivers.
United States v. Moriarty, 429 F.3d 1012 (11th Cir. 2005): three-part test for knowing and voluntary guilty plea.
United States v. Bushert, 997 F.2d 1343 (11th Cir. 1993) & United States v. Boyd, 975 F.3d 1185 (11th Cir. 2020): enforceability of sentencing appeal waivers.
United States v. Mosley, 173 F.3d 1318 (11th Cir. 1999) & United States v. Pease, 240 F.3d 938 (11th Cir. 2001): district court not obliged to forecast exact Guideline range when taking a plea.
Sapuppo v. Allstate Floridian Ins. Co., 739 F.3d 678 (11th Cir. 2014) and Cole v. U.S. Att’y Gen., 712 F.3d 517 (11th Cir. 2013): principles on abandonment of inadequately briefed issues.

The court wove these precedents into a cohesive rationale: Rule 11’s disclosures focus on statutory exposure, not speculative Guideline math; a properly conducted colloquy triggers a strong presumption of voluntariness; and poorly-developed appellate arguments are waived.

B. Legal Reasoning

Plain Error Framework. Because no contemporaneous objection existed, Simpkins had to demonstrate an error that was plain and that affected substantial rights. He failed at the first prong.
Rule 7(b) Compliance. The district court explicitly asked Simpkins whether he understood his right to grand-jury indictment and whether he wished to waive it. His in-court verbal assent, coupled with the written waiver, satisfied Moore.
Rule 11(b) Inquiry. The court meticulously reviewed the nature and elements of the § 1956(h) offense and the 20-year statutory maximum, fulfilling Rule 11(b)(1)(G)–(H).
No Duty to Anticipate Guideline Impact. Distinguishing statutory exposure from advisory-Guideline exposure, the panel reiterated that courts must state “any maximum possible penalty,” not every conceivable Guideline permutation. Guidance from Mosley and Pease controlled.
Effectiveness of Appeal Waiver. The colloquy highlighted the waiver’s scope and three narrow exceptions, satisfying Bushert/Boyd. Consequently, Simpkins could not challenge Guideline calculation or comparative sentence length on appeal.
Failure to Meet the Plain-Error Prejudice Prong. Even if there were some technical defect, Simpkins could not show that, but for the alleged error, he would have insisted on trial. The statutory cap dropped from 30 to 20 years, and he ultimately received 48 months—far below either maximum.

C. Impact of the Decision

1. Plea-Colloquy Practice. District judges in the Eleventh Circuit may rely on Simpkins to limit Rule 11 discussions to statutory maxima and fundamental rights; they need not itemise potential Guideline enhancements or compare ranges associated with alternative charging instruments, unless the plea agreement itself specifies a predicted range.
2. Prosecutorial Strategy. The decision implicitly endorses the use of superseding informations to streamline cases and incentivise cooperation. Defendants cannot later invalidate such waivers merely because the advisory Guidelines turned out worse than expected.
3. Defence Counsel Responsibilities. While courts have no obligation to forecast every Guideline implication, defence counsel do. The opinion signals fertile ground for ineffective-assistance claims where counsel fails to advise on Guideline repercussions—though Simpkins’ IAC argument was forfeited procedurally.
4. Appellate Waivers. Simpkins reinforces that appellate waivers will be enforced absent egregious ambiguity or coercion. Practitioners should draft and explain waivers with surgical precision.
5. Future Litigation. The ruling likely curtails “buyer’s remorse” challenges premised on post-plea Guideline surprises. It may also influence circuit splits on how expansive Rule 11 warnings must be, though it aligns with several circuits (e.g., 1st, 5th, 7th).

Complex Concepts Simplified

Waiver of Indictment (Rule 7(b)). A defendant can choose to skip the grand-jury phase and instead be charged by a prosecutor’s “information.” This often happens in negotiated pleas.
Superseding Information. A document replacing the original indictment, frequently containing fewer or different charges, filed when the defendant consents to proceed without a grand jury.
Plain Error Review. A strict appellate standard applied when the defendant failed to object at trial. The error must be clear (“plain”) and affect substantial rights, and even then, the court has discretion to ignore it.
Plea Colloquy. The in-court Q&A between judge and defendant ensuring the plea is voluntary and knowledgeable.
Presentence Investigation Report (PSI). A probation-office report calculating Guideline ranges and detailing the defendant’s background; used by the judge at sentencing.
Sentencing Guidelines vs. Statutory Maximum. The Guidelines produce an advisory range (e.g., 57-71 months), whereas the statute sets the absolute ceiling (e.g., 20 years). A court must state the latter during the plea; it need not compute the former.

Conclusion

United States v. Simpkins cements a pragmatic, text-driven approach to Rule 11: courts must apprise defendants of rights and statutory penalties, but they are not fortune-tellers of every conceivable Guideline outcome. The Eleventh Circuit’s opinion therefore:

validates indictment waivers executed in open court,
strengthens the enforceability of sentencing-appeal waivers, and
minimises collateral attacks predicated on post-plea Guideline surprises.

For litigants and judges alike, the key takeaway is clear: focus on statutory exposure, ensure the plea is free from coercion, and place the burden of Guideline forecasting where it belongs—on counsel, not the court.