Lawyers for Sean “Diddy” Combs urged an appeals court Thursday to overturn the hip-hop mogul’s prison term of more than four years for prostitution-related crimes, arguing that the sentencing judge improperly considered evidence related to more serious charges that a jury explicitly rejected through acquittal verdicts.
Combs, 56, was sentenced in October following a salacious trial that detailed the alleged “freak-offs” he organized—sexual marathons involving hired male escorts and his ex-girlfriend Casandra Ventura plus another unidentified woman. The case exposed intimate details of the music executive’s private life while raising complex legal questions about how judges may consider acquitted conduct when determining sentences.
According to Punch Nigeria, a jury acquitted Combs of the most serious charges against him—sex trafficking and racketeering—but convicted him of two counts of transporting people across state lines for prostitution. The mixed verdict created the legal controversy now before the appeals court about what evidence judges may properly consider when sentencing defendants for lesser crimes after juries reject more serious allegations.
The disgraced artist was not present at the Manhattan courthouse Thursday as defense lawyer Alexandra Shapiro sought to persuade a three-judge panel that Combs’s sentence of four years and two months was unfairly long for his crimes given that prosecutors failed to prove the most egregious allegations at trial.
“The evidence the judge was relying on was totally separate and, in fact, was acquitted conduct,” Shapiro argued, contending that District Judge Arun Subramanian should not have considered evidence that Combs made threats against Ventura and the other woman because it was related to the acquitted charges rather than the prostitution convictions.
Prosecutors disagreed and pointed to an instance where Combs showed Ventura he possessed videos of her engaging in sex parties hours before another “freak-off” in an apparent bid to ensure her continued participation. “These incidents are specifically tied to transportation,” prosecutor Christy Slavik told the court, arguing that the threats were relevant to the prostitution charges themselves rather than merely background to acquitted counts.
In a sign of the complex legal arguments, Slavik at one point drew an analogy involving pizza to highlight how certain “slices” of evidence were relevant to the ultimate sentencing decision—an unconventional comparison that illustrated the difficulty of parsing which evidence relates exclusively to acquitted charges versus conduct underlying convictions.
The court did not issue an immediate ruling in what Judge William Nardini characterized as an “exceptionally difficult case” raising novel questions that have not yet been considered by any U.S. appeals court. Combs is being held in the low-security Fort Dix prison in New Jersey and is scheduled for release in spring 2028 if his sentence stands.
Combs is also appealing his conviction, though that separate legal challenge was not discussed in detail Thursday. The appeals focused narrowly on sentencing issues rather than whether the jury reached correct conclusions about his guilt on the transportation charges.
Reuters documented that a U.S. appeals court appeared divided Thursday about Combs’s bid to overturn the hip-hop mogul’s prison sentence over prostitution charges in a case that raises novel legal questions about how judges consider conduct for which a defendant has been acquitted when determining punishment.
A three-judge panel of the Manhattan-based 2nd U.S. Circuit Court of Appeals heard arguments in Combs’s request to overturn his 2025 conviction and the sentence of four years and two months imposed by U.S. District Judge Subramanian. The arguments focused on the defense contention that Subramanian improperly considered evidence that Combs had threatened former girlfriends when determining the sentence last October.
Combs was found guilty by a jury last July on two counts of transportation to engage in prostitution. The verdict followed a seven-week trial in Manhattan federal court that centered on drug-fueled and days-long sexual performances, sometimes called “Freak Offs,” between two former girlfriends of the hip-hop mogul and male sex workers hired for the encounters.
However, jurors acquitted the Bad Boy Records founder on more serious sex trafficking and racketeering charges related to allegedly forcing the two former girlfriends—rhythm and blues singer Casandra Ventura and a woman known in court by the pseudonym Jane—to participate in the encounters while he watched, masturbated, and sometimes filmed the activities.
Combs, currently serving his sentence at Fort Dix, was not present at the hearing. Defense lawyer Shapiro argued Thursday that Subramanian should not have considered evidence that Combs threatened to release an explicit video of Ventura and threatened to cut off rent payments for Jane when deciding on the sentence because that evidence involved the criminal counts rejected by the jury.
“The jury did not authorize punishment for sex trafficking or racketeering conspiracy,” Shapiro emphasized, arguing that considering acquitted conduct for sentencing purposes effectively allows prosecutors to obtain punishment for charges they failed to prove beyond reasonable doubt.
Prosecutor Slavik countered that Subramanian was correct to consider the threats because they were relevant to the prostitution counts as well as the acquitted charges. “Judge Subramanian properly considered the aggravated manner in which the defendant carried out his Mann Act offenses,” Slavik stated, referring to the criminal statute that criminalizes transportation across state lines for prostitution purposes.
Judge M. Miller Baker, a member of the 2nd Circuit panel, appeared sympathetic toward the defense arguments, noting that prosecutors did not emphasize the Mann Act charges at trial despite now seeking to uphold a sentence based partly on conduct related to those charges. “It was just a sideshow,” Baker observed about the prostitution charges relative to the sex trafficking allegations that dominated the trial.
“Why shouldn’t we hold you to what you argued to the jury?” Baker questioned Slavik, suggesting prosecutors should not be allowed to minimize charges at trial then rely on them heavily for sentencing purposes when more serious allegations fail.
Judges Nardini and Sarah Merriam, the panel’s two other members, appeared more skeptical of the defense arguments but also posed probing questions of Slavik about the boundaries between evidence supporting convictions versus evidence related exclusively to acquitted conduct. Nardini confirmed the case raises questions that have not yet been considered by any U.S. appeals court, making the eventual ruling potentially significant for sentencing practices nationwide.
“This is an exceptionally difficult case,” Nardini acknowledged, recognizing the legal complexity of determining which evidence judges may properly consider when sentencing defendants convicted of some charges but acquitted of others arising from the same underlying conduct.
Combs has acknowledged abusing his former girlfriends but maintained that incidents of what he characterized as domestic violence were separate from the sexual performances at issue in the case, which he insisted were consensual. The acknowledgment of abuse complicates his legal position by admitting wrongdoing even while disputing the specific criminal charges prosecutors pursued.
He is currently scheduled for release from prison on April 15, 2028, according to Bureau of Prisons records, though that date could change if appeals courts overturn either his conviction or sentence and order new proceedings.
The case illustrates ongoing tension in American criminal justice between jury verdicts that specifically reject certain allegations and judicial sentencing discretion that allows consideration of broader conduct patterns when determining appropriate punishment. Federal sentencing guidelines grant judges substantial authority to consider “relevant conduct” beyond elements of convicted offenses, creating potential for defendants to face punishment influenced by allegations juries rejected.
Legal scholars have debated for decades whether considering acquitted conduct at sentencing violates defendants’ constitutional rights by allowing punishment without proof beyond reasonable doubt. The Supreme Court has not definitively resolved the question, leaving appellate courts to navigate case-by-case determinations about which evidence crosses the line from legitimate sentencing consideration to improper end-run around jury acquittals.
For Combs, the legal arguments carry enormous personal stakes. If the appeals court concludes that Subramanian improperly inflated his sentence by considering threats related to acquitted charges, his prison term could be substantially reduced. Conversely, if the court upholds the sentence, he will serve the full four years and two months unless his separate appeal of the underlying convictions succeeds.
The three-judge panel’s apparent division during oral arguments suggests the eventual ruling could be close, potentially producing dissenting opinions that further develop the law in this unsettled area. Whether the court issues its decision within weeks or months remains uncertain, though federal appeals courts typically rule within six to twelve months of oral arguments.
For Ventura, Jane, and other women who testified about Combs’s alleged abuse, the appellate proceedings may feel like prolonged legal battles denying them closure after already enduring the trauma of publicly recounting intimate violations during trial. Whether they view potential sentence reduction as injustice or accept it as legitimate correction of legal error likely depends on their perspectives about criminal justice system fairness versus desires for maximum punishment of someone they believe harmed them profoundly.
As Combs serves his sentence while awaiting appellate rulings that could alter both his punishment and conviction, the case continues generating legal precedents that will influence how courts nationwide handle sentencing for defendants who face multiple charges arising from related conduct when juries convict on some counts while acquitting on others.
Reuters/Punchng
