Sean “Diddy” Combs is mounting a major challenge to his four-year prison sentence from a federal prison in New Jersey, arguing that the judge punished him for conduct a jury refused to criminally convict.
On December 23, 2025, his lawyer, Alexandra Shapiro, filed an 84-page brief with the 2nd U.S. Circuit Court of Appeals in Manhattan, calling the 50‑month term “illegal, unconstitutional, and a distortion of justice,” according to court records reviewed by BBC News and the New York Times.
The Split Verdict and Mann Act Convictions
In July 2025, after roughly 13 hours of deliberations across three days, a Manhattan jury delivered a sharply divided outcome. Jurors convicted Combs on two counts of transportation for prostitution under the Mann Act, a more than century‑old statute that makes it a crime to move people across state lines for unlawful sexual activity. They cleared him, however, of the three most serious charges: racketeering conspiracy and two counts of sex trafficking, offenses prosecutors had said could have led to a life sentence.
Federal prosecutors had accused Combs of arranging travel for girlfriends and paid male sex workers so they could engage in drug‑fueled sexual encounters he recorded, conduct they said violated the Mann Act. Each count carries a maximum of 10 years in prison. In their appeal, Combs’ lawyers argue that in comparable Mann Act cases, even when coercion is proven, typical sentences are under 15 months, and they say defendants on average receive about 14.9 months. They contend that by comparison, Combs’ 50‑month term is the harshest ever imposed on a similarly situated defendant.
Inside the Sentencing Battle
At the October 3, 2025, sentencing hearing, U.S. District Judge Arun Subramanian handed down a 50‑month prison term and a $500,000 fine. Reporting from the courtroom describes the judge acknowledging letters and testimony about Combs’ philanthropy and family support but insisting that “a history of good works can’t erase your record.” He said a substantial sentence was needed to signal that abuse and violence against women would meet “real accountability”.
The sentencing capped months of pretrial and trial‑stage disputes over how dangerous or flight‑prone Combs might be. Before trial, he proposed a $50 million bond secured partly by his $48 million Miami mansion, which he had fully paid off by wiring $18 million to clear the mortgage in August 2024. The package also offered GPS monitoring, restricted movement to Miami and New York, and keeping his private jet grounded in Los Angeles. Judge Subramanian rejected the bid, finding Combs had not shown by “clear and convincing evidence” that he posed no danger or risk of flight.
In explaining both his bail decision and the sentence, the judge pointed to evidence of violence. That included testimony from an anonymous former girlfriend, “Jane,” who said Combs choked and dragged her in June 2024 while he was already under federal investigation. Prosecutors also relied on widely viewed hotel surveillance footage from 2016, released by CNN in May 2024, appearing to show Combs kicking and dragging ex‑girlfriend Casandra “Cassie” Ventura in a hallway of the InterContinental in Los Angeles.
Acquitted Conduct and a New Federal Rule
The defense appeal argues that Judge Subramanian crossed a legal line by treating himself as a “thirteenth juror.” According to the brief, he relied on allegations tied to the racketeering and sex‑trafficking counts the jury rejected, effectively finding that Combs coerced, exploited, and forced his girlfriends into sex. Shapiro’s team says that approach “defied the jury’s verdict”.
Their claim centers on a major 2024 change in federal sentencing policy. In November 2024, an amendment to the U.S. Sentencing Guidelines took effect, barring judges from using “acquitted conduct” to increase prison terms. The bipartisan U.S. Sentencing Commission had unanimously approved the reform earlier that year. Commission Chair Judge Carlton W. Reeves underscored the principle by saying, “Not guilty means not guilty”.
Before the change, federal judges could consider conduct underlying charges that had resulted in acquittal, using a lower “preponderance of the evidence” standard rather than the “beyond a reasonable doubt” standard required to convict. Defense lawyers and lawmakers in both parties had long argued that this practice undercut the role of juries and basic fairness. Prosecutors in Combs’ case counter that he is not being punished for acquitted offenses but that his sentence must reflect “the nature and circumstances” of the Mann Act crimes for which he was convicted, including what they describe as a years‑long pattern of abuse and a lack of remorse.
Testimony, Settlement, and Competing Sentencing Requests
The trial featured extensive testimony from Cassie Ventura, who spent nearly 20 hours on the stand over four days in May 2025. She told jurors Combs controlled her appearance, finances, and access to electronic devices and forced her into hundreds of sexual encounters with male escorts during multi‑day “freak‑offs.” According to her account, some of these episodes lasted four days or more, left her dehydrated, and required recovery from heavy drug use.
Ventura also revealed, for the first time in open court, that Combs had paid $20 million to settle her November 2023 civil lawsuit. She testified that before suing, she had offered him the rights to her unpublished book for $30 million. Asked whether she would give back the settlement if it meant avoiding the “freak‑offs,” she answered that if she had never endured them, she would have had “agency and autonomy” and would not have had to struggle to reclaim it.
Ahead of sentencing, prosecutors filed a 164‑page memo urging a minimum term of 135 months—just over 11 years—arguing Combs was “unrepentant” and pointing to what they described as decades of alleged abuse. His attorneys countered with a request for 14 months, saying the roughly 13 months he had already spent at Brooklyn’s Metropolitan Detention Center amounted to sufficient punishment, particularly given typical Mann Act outcomes.
Appeal Stakes and Life Behind Bars
Combs is now housed at the Federal Correctional Institution at Fort Dix, New Jersey, the largest single federal prison in the country, with more than 4,100 male inmates. Reporting indicates he works in the laundry and is assigned to the facility’s Residential Drug Abuse Treatment Program unit rather than the general population. Bureau of Prisons records initially projected a May 2028 release, but rule violations reportedly moved that to June 4, 2028. With the maximum “good time” credits—up to 54 days off per year served—a 50‑month term can translate into about 42 to 43 months behind bars.
Leading his appeal is Alexandra Shapiro, a former Supreme Court clerk for Justice Ruth Bader Ginsburg and co‑founder of the New York litigation boutique Shapiro Arato Bach. She has previously secured reversals in white-collar cases at both the Supreme Court and the 2nd Circuit, an experience that could prove significant as the panel weighs this challenge to the new acquitted-conduct rule.
Combs’ lawyers have asked the appeals court to acquit him, order his immediate release, or send the case back for resentencing under the 2024 guideline change. The court has not yet scheduled oral arguments. Legal analysts say the outcome could ripple far beyond Combs, potentially triggering resentencings for other federal inmates whose punishments were increased based on acquitted conduct. For now, the case stands as an early and closely watched test of how firmly the federal courts will enforce the idea that when a jury says “not guilty,” that verdict still shapes what happens at sentencing.
Sources
BBC News, “Sean ‘Diddy’ Combs files appeal asking for his immediate release,” December 24, 2025
New York Times, “Sean Combs’s Lawyers File Appeal, Arguing His Sentence Is Illegal,” December 23, 2025
CNN, “Sean ‘Diddy’ Combs sentenced to over 4 years in prison,” October 3, 2025
U.S. Sentencing Commission, “2024 Acquitted Conduct Amendment In Brief”
Reuters, “US panel prohibits judges from sentencing for ‘acquitted conduct,’” April 17, 2024
People Magazine, “8 Shocking Bombshells from Cassie’s Testimony at Diddy Trial,” December 3, 2025