Joshua Goldman
Joshua Goldman
min read · October 3, 2025 · Entertainment

Diddy's Miami Speaking Gig: A Legal Gamble or Hubris?

Diddy, pictured in Miami in March 2024, booked a speaking arrangement in the Florida city next week, prosecutors said at his sentencing Friday. He allegedly did so despite facing up to 20 years behind bars for federal prostitution offenses

DISGRACED SEAN 'DIDDY' COMBS BOOKS SPEAKING ARRANGEMENT IN MIAMI DESPITE FACING 20 YEARS BEHIND BARS

The plot thickens in the saga of Sean "Diddy" Combs, the embattled rapper who's been convicted of federal prostitution offenses. Despite facing up to 20 years behind bars, Diddy, 55, has booked a speaking engagement in Miami, under the assumption that he'd be a free man soon. This arrogant move has left prosecutors and judges alike fuming.

According to court documents obtained by TheScholarlyNote.com, Diddy's defense team claimed that he had scheduled a teaching position in Miami next week to give guidance to prisoners about entrepreneurship. Yes, you read that right - the same mogul who's been accused of running a sex trafficking ring is now offering to teach life skills and business acumen to inmates.

A court sketch of Diddy in July. Today the rapper was warned evidence pertaining to crimes he was not sentenced for could influence his final punishment

But don't be fooled by Diddy's attempt to rebrand himself as a saintly do-gooder. Prosecutors are not buying it. In fact, they're calling his actions "the height of hubris" and accusing him of assuming that the court will ignore the law and let him off scot-free.

"It shows he's not respecting the law," prosecutor Mary Slavik told the hushed Manhattan Federal Courthouse. "He's making a mockery of the justice system."

Diddy, who was convicted in July, faces a maximum of 20 years behind bars for transportation to engage in prostitution of his ex-girlfriend Cassie Ventura and another unnamed woman. But despite the severity of the charges, Diddy seems to be playing it cool.

Diddy's trial captured national attention earlier this year as the jury heard weeks of gut-wrenching testimony from his ex-girlfriend Cassie Ventura (seen together), where she alleged that she was coerced into marathon 'freak off' sexual performances during their relationship

In a bizarre promo video released by his attorneys just hours before sentencing, Diddy is portrayed as a loving father and dedicated philanthropist. The 11-minute clip shows him with his children during their childhoods, interspersed with footage of him meeting fans and recording music.

But beneath the surface, Diddy's team is frantically trying to salvage his image ahead of what could be a lengthy prison sentence. His attorneys have been working overtime to humanize their client, showcasing his charter school in Harlem where he's seen speaking with young students and celebrating lifetime achievement awards.

However, it seems that Diddy's attempts to spin his narrative are not having the desired effect. On the eve of sentencing, two new alleged victims came forward with fresh sexual assault allegations against him - a man and a woman who filed civil lawsuits against the disgraced mogul.

Diddy, seen in a court sketch, has languished in the Metropolitan Detention Center in Brooklyn ever since he was arrested in September 2024

Diddy has been locked up in Brooklyn's Metropolitan Detention Center since September 2024, where he's been housed alongside other high-profile inmates like accused CEO shooter Luigi Mangione and convicted crypto fraudster Sam Bankman-Fried.

As the sentencing hearing gets underway, Judge Arun Subramanian is expected to consider evidence from Diddy's crimes - including the alleged sex trafficking of Cassie Ventura. But what will ultimately decide Diddy's fate is still unclear.

Prosecutors have recommended an 11-year sentence for Diddy, while his defense team is pushing for a mere 14 months behind bars. The judge can use his discretion to decide how long Diddy should be sentenced for - and it's anyone's guess whether he'll go longer or shorter than the recommended term.

One thing is certain, though: Sean "Diddy" Combs is in for the fight of his life. And with fresh allegations piling up against him, it's clear that this saga is far from over.