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Diddy Prison Fight: Former Rikers Island Warden Says Brawl Could Impact Release Date

Published: 07/24/2026

Diddy's recent prison fight could end up undoing some of the good behavior credit he's already racked up ... so says the former warden of Rikers Island. Howard Robertson -- a former New York City Department of Correction employee who rose to the top job at one of New York's most notorious federal…

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Diddy Wants Woman Who Sued Him to Pay for 'Frivolous' Lawsuit

Published: 07/20/2026

Diddy says one of the lawsuits against him is so baseless that he's now asking a judge to make the woman who sued him ... and her lawyers ... to pay up. According to court docs obtained by TMZ, Diddy is asking a federal judge to sanction Grace O'Marcaigh and her attorneys, claiming they filed what…

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Diddy's Twin Daughters Jessie and D'Lila Say He's 'Amazing' Father

Published: 07/17/2026

Forget what you think you know about Diddy as a boss or a boyfriend ... his 19-year-old twin daughters Jessie and D'Lila say the guy's an "amazing" father. The teens sat down with Entertainment Tonight and had nothing but praise for the disgraced musician, who is currently locked up after being…

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Sean 'Diddy' Combs Sells His Star Island Estate For $55 Million

Published: 07/15/2026

Sean "Diddy" Combs just unloaded one of his crown jewel properties on Miami's Star Island, selling it for a whopping $55 million, TMZ has confirmed.  The waterfront property -- at 1 West Star Island -- was purchased by JFStar LLC, a real estate holding company based in Newport News, Virginia…

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Diddy Is 'Incredibly Proud' Of Twin Daughters New Streetwear Brand

Published: 07/07/2026

Diddy's twin daughters Jessie and D'Lila are making moves while their father sits behind bars at Fort Dix ... 'cause TMZ has learned they're launching a new streetwear brand. Jessie and D'Lila officially launched their fashion brand Tuesday ... it's called "12TWINTY1" ... and it's a unisex brand…

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Diddy Caught on Video During Daily Walk Inside Federal Prison

Published: 07/07/2026

Diddy's getting his steps in behind bars ... TMZ has obtained video showing him out for one of his daily walks inside FCI Fort Dix. The footage is quick, but it's a rare glimpse of the Bad Boy founder on prison grounds in New Jersey. Take a look ... Diddy can be seen making his rounds inside the…

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Cassie: Ex-Male Escort Denies Threatening Diddy’s Ex in TikTok

Published: 07/07/2026

One of the male escorts involved in freak-offs with Cassie is telling a judge he never threatened Diddy’s ex ... despite her claims otherwise ... TMZ has learned. Clayton Howard, former male escort-turned-law student, filed a declaration in his case against Cassie and Diddy. As TMZ first…

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President Donald Trump Reportedly Still Mulling Over Diddy Pardon

Published: 07/03/2026

Donald Trump might be getting ready to break out the pardon pen again ... and one name that's apparently still floating around behind closed doors is Sean "Diddy" Combs. Trump was expected to huddle with advisers Friday over a new batch of pardons ... and CBS News reports Diddy remains one of…

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Star of Viral Diddy Staredown Meme Elijah Connor Hits the TMZ Brunch Bus

Published: 07/01/2026

The TMZ Brunch Bus was in a for a treat when Elijah Connor stopped by ... because he serenaded the guests all around town. The R&B singer showed off the star power in his family -- he's Prince's younger cousin -- with a live performance of his new single. Elijah's biggest claim to fame might…

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Vice President JD Vance Calls Diddy A 'Great Christian Theologian'

Published: 06/25/2026

JD Vance can't think of any better Christian theologian than Diddy ... just kidding. Take a look at the video ... the veep visited the Richard Nixon Library Thursday, when he was asked about a chapter in his memoir titled "More Money, More Problems" -- a reference to Diddy's song with The…

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Diddy's Company Sued For Allegedly Backing Out of Star Island Home Sale

Published: 06/19/2026

Diddy's company is being sued after allegedly failing to close a multi-million dollar deal to sell his home on Star Island near Miami. A man named John Franklin is suing 1 West Star Island LLC -- the corporation which technically owns Diddy's mansion in the affluent neighborhood ... claiming he…

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Diddy's Projected Prison Release Date Moved Up to Early 2028

Published: 06/16/2026

Diddy might be trading a federal prison for a recording studio sooner than expected ... because the music mogul's projected prison release date has been moved up. The music producer and rapper is now scheduled to be released from federal lockup on February 23, 2028 ... according to the Federal…

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