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Diddy’s Prison Release Date Confirmed Amid Appeal Plans

By: AllHipHop Staff Updated Oct 27, 2025 at 2:00pmCategory: News
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Diddy is scheduled to be released from prison on May 8, 2028, after serving a 50-month sentence for prostitution-related charges under the Mann Act.

Diddy

White House Trashes TMZ Over Report Of Potential Diddy Pardon

By: AllHipHop Staff Updated Oct 21, 2025 at 6:03pmCategory: News
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Trump denied plans to pardon Diddy after TMZ claimed he considered clemency for the convicted mogul serving 50 months for prostitution charges.

Donald Trump, Melania Trump and Sean Diddy Combs

Druski Baby Oil Lawsuit Gets Slippery—Over Grandma’s Phone

By: Grouchy Greg Watkins (@GrouchyGreg) Updated Oct 20, 2025 at 9:30pmCategory: Exclusives
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Ariel Mitchell challenged Druski’s alibi by revealing his phone was under his grandmother’s name, raising doubts about his location.

Druski

EXCLUSIVE: Judge Says He Cannot Recommend Fort Dix As Diddy’s Choice Of Prison

By: Grouchy Greg Watkins (@GrouchyGreg) Updated Oct 8, 2025 at 9:30pmCategory: Exclusives
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Diddy’s request for a specific prison was denied by a judge who said only a general location and program recommendation can be made to the Bureau of Prisons.

Diddy

Druski Baby Oil Lawsuit Involving Diddy Slipping Away, As Lawyers Seek To Drop Accuser

By: Nolan Strong Updated Oct 8, 2025 at 7:00pmCategory: News
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Druski’s name may soon be cleared entirely as the lawsuit tying him to a 2018 assault falls apart after lawyers dumped the accuser.

Druski

Lawyers Plan To Appeal Diddy’s Prison Sentence, Blast Judge

By: Mike Winslow Updated Oct 5, 2025 at 6:00pmCategory: News
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Diddy will challenge his federal conviction after being sentenced to over four years in prison and fined $500K for transporting people for sex.

Diddy

Diddy Intern Claims He Was Drugged, Assaulted & Ended Up With HIV

By: Mike Winslow Updated Oct 5, 2025 at 4:03pmCategory: News
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Diddy faced another lawsuit as a former intern claimed he was drugged and raped at a 2014 after-party in L.A., later learning he had HIV.

Diddy

Suge Knight Comments On Diddy Sentencing: “Was Waiting For Him To Shake That Ass”

By: Mike Winslow Updated Oct 5, 2025 at 2:03pmCategory: News
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Suge Knight accused Diddy of being protected by federal authorities and mocked his courtroom presentation.

Diddy Suge Knight

Aubrey O’Day Speaks Out After Diddy Sentenced to Four Years

By: Mike Winslow Updated Oct 4, 2025 at 6:02pmCategory: News
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Aubrey O’Day addressed Sean “Diddy” Combs’ sentencing by urging young performers to recognize red flags and walk away from exploitative power dynamics in the industry.

Aubrey O'Day Diddy

Cassie Ventura Responds To Diddy’s 50-Month Prison Sentence: “Nothing Can Undo The Trauma”

By: Nolan Strong Updated Oct 4, 2025 at 4:02pmCategory: News
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Cassie Ventura responded through her attorney after Diddy was sentenced to 50 months in prison for domestic violence, marking a major moment in the case.

Cassie and Diddy

Diddy Heading To Prison, Judge Gives Him Hard Time At Sentencing

By: Grouchy Greg Watkins (@GrouchyGreg) Updated Oct 3, 2025 at 4:42pmCategory: News
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Diddy was sentenced to federal prison after a jury found him guilty of transporting women across state lines for prostitution.

Diddy

WATCH: Diddy Drops Redemption Video Hours Before Sentencing Hoping To Sway Judge

By: Grouchy Greg Watkins (@GrouchyGreg) Updated Oct 3, 2025 at 11:03amCategory: News
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Diddy released a last-ditch video and heartfelt letter to the judge before sentencing, hoping to spotlight his personal growth and positive impact.

Diddy

EXCLUSIVE: Diddy Set To Launch Teaching Tour In October—If He’s Sprung From Jail

By: Grouchy Greg Watkins (@GrouchyGreg) Updated Oct 2, 2025 at 11:00pmCategory: News
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Diddy may trade his jail cell for a classroom next month, but only if a federal judge agrees to a lighter sentence on October 3.

Diddy

Diddy Writes Letter To Judge Before Sentencing: “The Old Me Died In Jail”

By: Nolan Strong Updated Oct 2, 2025 at 7:00pmCategory: News
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Diddy addressed the court in a personal letter ahead of his sentencing, saying “the old me died in jail” as he asked for leniency.

Diddy

EXCLUSIVE: Convicts Diddy & Billionaire MAGA Ally Miles Guo Plot AI Platform As Jail Buddies

By: Grouchy Greg Watkins (@GrouchyGreg) Updated Oct 2, 2025 at 2:00pmCategory: Exclusives
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Diddy and convicted billionaire fraudster Miles Guo are reportedly planning an AI platform from behind bars.

Diddy

EXCLUSIVE: Diddy Tries To Silence Mia From Speaking At Upcoming Sentence

By: Grouchy Greg Watkins (@GrouchyGreg) Updated Oct 1, 2025 at 2:31pmCategory: Exclusives
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Diddy attempted to block Mia from speaking at his sentencing, but the judge will now decide whether her voice will be heard in court on Friday.

Diddy

EXCLUSIVE: Diddy Allowed To Wear Slacks, Sweater & Shoes With No Laces At Sentencing

By: Grouchy Greg Watkins (@GrouchyGreg) Updated Sep 30, 2025 at 11:00pmCategory: Exclusives
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Diddy received rare approval to wear civilian clothing at his sentencing, raising questions about how the judge may view his legal situation.

Sean "Diddy" Combs

BREAKING: Judge Shoots Down Diddy’s Attempt To Have Prostitution Conviction Dropped

By: Nolan Strong Updated Sep 30, 2025 at 8:32pmCategory: News
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Diddy was denied a motion to overturn two Mann Act convictions, leaving him facing up to 20 years in prison ahead of next month’s sentencing.

Diddy

EXCLUSIVE: Diddy Ordered To Explain Why He Needs Fancy Wardrobe For Sentencing

By: Grouchy Greg Watkins (@GrouchyGreg) Updated Sep 25, 2025 at 8:00pmCategory: Exclusives
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Diddy was told by a federal judge he must explain why he should be allowed to wear civilian clothes at his sentencing in October 2025.

Diddy

EXCLUSIVE: Inmates Rave Over Diddy’s Free Game Class In Jail

By: Grouchy Greg Watkins (@GrouchyGreg) Updated Sep 25, 2025 at 1:31pmCategory: Exclusives
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Diddy has earned praise from inmates at Brooklyn’s MDC for teaching a class that’s helping them build discipline and a plan for life.

Diddy

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