Sean Combs, still widely known as Diddy or Puffy, remains at the center of major headlines in late October 2025, marking a dramatic crumbling of a star once at the pinnacle of music and business. Diddy is currently serving a 50-month federal prison term after his conviction on charges of transportation to engage in prostitution, a result of a high-profile New York trial earlier this year. According to Complex and corroborated by federal Bureau of Prisons records, Diddy’s expected prison release date is May 8, 2028, though there remains speculation about appeals or sentence reductions that could alter this timeline. While rumors have circulated about a possible presidential pardon from Donald Trump, the White House spokesperson recently dismissed these outright, stating there is “zero truth” to the speculation and emphasizing that the President is the only decision maker on clemency matters.

Inside prison, reports from Daily Mail sources paint a dangerous picture, including allegations that Diddy recently woke up with a knife pressed to his throat during an intimidation attempt by a fellow inmate. While not physically harmed, these threats serve as stark reminders of his high-profile status even while serving time.

Diddy’s fall from grace included not only criminal trials but also a series of raids on his Los Angeles and Miami properties in March, actions related to ongoing federal sex trafficking investigations as reported by Fox 11 and corroborated by Homeland Security officials. His attorney decried the raids as “a gross overuse of military force,” asserting that neither Diddy nor his children were arrested and maintaining his innocence on all allegations. The raids brought renewed scrutiny to his strained business and personal affairs, and were followed by several lawsuits in recent months alleging sexual assault and abuse, accusations Diddy continues to vigorously deny.

As a consequence of the mounting legal and financial pressure, Diddy has listed his famed Holmby Hills mansion in LA—a sprawling estate once valued at over $60 million. People Magazine confirmed the listing, and sources close to Diddy say selling it was part of a planned transition with his daughters reaching adulthood, though the context of the federal raids is impossible to ignore.

Notably, the mogul’s business empire, once valued by Forbes at upwards of $740 million, suffered significant blows in the past year. In January, ongoing disputes with spirits giant Diageo were finally resolved, with the company now having sole ownership of Ciroc vodka and DeLeón tequila, stripping Diddy of a long-standing revenue stream from the alcohol business.

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