Freeman v. United States
The Court ruled that a man who pleaded guilty under a plea deal specifying a 106-month sentence could still seek a shorter sentence after the government retroactively lowered the crack-cocaine sentencing guidelines his deal was tied to.
The splintered ruling means people who struck this kind of fixed-sentence plea deal are not automatically barred from later sentence cuts, though the justices could not agree on exactly why, leaving lower courts to sort out which plea deals qualify.
How it got here: A federal trial court denied Freeman's request for a sentence cut; the Sixth Circuit affirmed, holding such fixed-sentence plea deals categorically ineligible; Freeman appealed to the Supreme Court.
The Case in Depth
What happened
William Freeman was charged with drug and gun crimes. He and prosecutors signed a plea deal under a rule that lets both sides agree on an exact sentence, which then binds the judge if accepted. They agreed on 106 months, based partly on the sentencing guidelines then in effect for crack cocaine. Years later, the government lowered those guidelines to fix a disparity with penalties for powder cocaine, and Freeman asked for a shorter sentence.
The question before the Court
If a defendant pleads guilty under a plea deal that locks in a specific prison sentence, can he still ask for a shorter sentence later when the government lowers the relevant sentencing guidelines?
The Court's answer
Yes — a majority of the Court agreed Freeman could seek a shorter sentence, but the justices split on why. Four justices (the plurality) said that whenever a judge's decision to accept and impose a plea-deal sentence is actually shaped by the sentencing guidelines, that sentence counts as "based on" those guidelines, making the defendant eligible for a cut when the guidelines later drop — regardless of the deal's wording.
Justice Sotomayor, providing the fifth vote, disagreed with that reasoning. She said a plea-deal sentence is based on the agreement itself, not the judge's guidelines calculation — but ruled that Freeman still qualified because his agreement explicitly used a guidelines range to build the 106-month figure. Four dissenting justices agreed with her general approach but not her exception, and would have found Freeman ineligible entirely.
Curious how the Court got there? See the step-by-step legal reasoning →
Why it matters
Thousands of federal prisoners who pleaded guilty under fixed-sentence plea deals tied to the old, harsher crack-cocaine guidelines may now be able to ask judges for shorter sentences. But because no single legal rationale won five votes, lower courts must now work out case-by-case which plea agreements qualify, creating uncertainty for prosecutors, defense lawyers, and judges handling these motions.
What changes now
The case returns to the lower courts, where a district judge will decide whether to actually grant Freeman a reduced sentence under the guidelines that took effect after his plea deal — the Supreme Court only established his eligibility to make that request. Because no rationale commanded five votes, lower courts will need to work out on a case-by-case basis which plea agreements qualify for this kind of relief going forward.
What this does not decide
The Court did not decide whether Freeman should actually receive a reduced sentence, only that he may ask for one. Because the plurality, Sotomayor's concurrence, and the dissent all used different reasoning, the decision does not establish one clear, agreed-upon test for when other fixed-sentence plea deals qualify for this kind of relief.
Concurrences and dissents
Concurrence — Justice Sotomayor
Sotomayor agreed Freeman should win but for a different reason: she said a plea-deal sentence is based on the agreement itself, not the judge's guidelines math, so most defendants with these fixed-sentence deals cannot seek reductions. She carved out an exception for agreements that expressly use a guidelines range to build the specific sentence figure, which she found true here because the parties combined the range's low end with a separate mandatory minimum.
Dissent — Justice Roberts
Roberts agreed with Sotomayor that plea-deal sentences are based on the agreement, not judicial guidelines calculations, but rejected her exception as arbitrary and unworkable, arguing there is no reliable way to tell whether an agreement's specific number was truly derived from a guidelines range or from other bargaining considerations like dropped charges or witness credibility concerns. He would have held Freeman ineligible entirely and warned the ruling would create confusion for lower courts.
How the Court got there
The legal reasoning, step by step
- The plurality applied ordinary sentencing law's command that judges impose a sentence 'sufficient, but not greater than necessary' in light of the sentencing guidelines — a framework agency-issued benchmarks meant to guide, not replace, judicial discretion.
- The plurality reasoned that even when parties agree to a specific sentence under a plea rule allowing binding sentence agreements, the judge must still independently consult the guidelines before accepting the deal, because a governing policy statement forbids accepting such an agreement without first weighing the applicable guidelines range.
- Because the sentencing hearing transcript showed the judge expressly considered the guidelines range before imposing Freeman's sentence, the plurality concluded his sentence was 'based on' that range and thus eligible for reduction when the range was later lowered.
- Justice Sotomayor, providing the decisive fifth vote, rejected the plurality's judge-focused test, reasoning instead that a plea-deal sentence is grounded in the binding agreement itself, since the judge has no power to alter the agreed term once accepting the deal.
- Sotomayor concluded that an exception applies when the agreement's own text expressly ties the specific sentence to a guidelines range, because in that narrow circumstance the range itself functions as the basis for the number the parties chose.
- Applying that exception, Sotomayor found Freeman's agreement combined the low end of an identified guidelines range with a separate mandatory minimum to produce the 106-month figure, so his sentence was 'based on' that range and eligible for reduction.
Doctrinal impact
Cases affected by this decision
Reaffirms Dillon v. United States (560 U. S. 817)
The opinion relies on Dillon's holding that courts must follow the Sentencing Commission's policy statement to determine eligibility for sentence reductions.