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Diddy Winners v Losers

Diddy Trial Highlights From Seventh Day of Testimony

Published: 05/20/2025
Prosecutors seemed to be getting more testimony geared towards the racketeering charge against Diddy in the seventh day of witnesses on the stand ... but there were still some outlandish stories told in court too. The wildest testimony came courtesy of a male exotic dancer nicknamed "The Punisher"…
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p diddy cassie the punisher main getty composite

Exotic Male Dancer 'The Punisher' Writes About Cassie-Diddy Encounters in Book

Published: 05/20/2025
Sharay Hayes, an exotic male dancer known as "The Punisher," included his sexual experiences with Cassie and Diddy in his memoir about erectile dysfunction ... and it's very graphic. Hayes took the stand Tuesday in Diddy's federal criminal trial in NYC and he told the jury he wrote about Diddy and…
... Read More
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Kid Cudi Scheduled to Testify in Diddy Trial

Published: 05/20/2025
Kid Cudi's been name-dropped several times in witness testimony in the Diddy trial in NYC ... and the rapper will soon take the witness stand himself. Federal prosecutors said Tuesday they plan to call Kid Cudi as a witness, possibly as early as Wednesday ... though based on the witness list for…
... Read More
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50 Cent Poses in 'Free Diddy' Shirts, Comments on Cassie's Mother

Published: 05/20/2025
50 Cent is still highly entertained by Diddy's trial and the magic of A.I., but he can't believe the details spilling from the case ... especially the deets involving Cassie's mother!!! Following the revelation on Tuesday that Diddy once caused Cassie's parents to take out a $20K home equity loan…
... Read More
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Exotic Male Dancer 'The Punisher' Recalls First Encounter With Diddy, Cassie

Published: 05/20/2025
Sharay Hayes, an exotic male dancer known as "The Punisher," is testifying for the prosecution in the Diddy trial ... telling the jury about the first encounter he had with Diddy and Cassie ... saying the couple hired him to create a sexy erotic scene for them. Hayes says he was first hired in…
... Read More
cassie ventura regina ventura p diddy main getty

Cassie's Mom Testifies She Wired Diddy $20K During Daughter's Kid Cudi Relationship

Published: 05/20/2025
Regina Ventura, Cassie's mother, appeared in a Manhattan courtroom Tuesday to testify in Diddy's federal sex trafficking and racketeering trial in NYC ... and she revealed some shocking details about her daughter's relationship with the incarcerated defendant. On the stand, Regina confirmed her…
... Read More
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Diddy's Ex-Assistant Says Diddy Told Him to Keep His Hands Off Women

Published: 05/20/2025
David James, a former personal assistant to Diddy, says his boss once gave him some ironic advice ... warning him not to get violent with women. During cross-examination from Diddy defense attorney Marc Agnifilo, James admitted he got into a physical altercation with one of Diddy's former chefs, a…
... Read More
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Diddy's Former Assistant Testifies He Was 'Diddy-Bopping' on Drugs

Published: 05/20/2025
Today is the seventh day of testimony in Diddy's federal sex trafficking and racketeering trial in New York City ... David James, a former personal assistant to the rap mogul, is still on the witness stand -- and he testified to what he described as "Diddy-bopping" ... which he described as taking…
... Read More
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Diddy Prosecutors Release Photos Showing Faces of 'Freak Off' Sex Workers

Published: 05/19/2025
5/22/25 6:20 PM PT -- In an earlier version of this story -- and others on TMZ.com -- we incorrectly identified one of the photos of the alleged sex workers as "Jules." The man prosecutors labeled "Exhibit 2A-628" is not Jules, the man Cassie testified was with Diddy and her at the L.A.…
... Read More
0519-Cassie-Ventura-Pregnant-With-BF-PRIMARY

Cassie Ventura, Alex Fine Seen Out for First Time Since Diddy Trial Testimony

Published: 05/19/2025
Cassie Ventura and husband Alex Fine were seen out Monday, for the first time since the singer testified in Diddy's federal sex trafficking trial in NYC last week. The married couple was seen exiting their residence in the city looking casual ... Cassie's going incognito in oversized dark…
... Read More
Diddy Winners Losers

Diddy Trial Highlights From 6th Day of Testimony

Published: 05/19/2025
The sixth day of witness testimony in the Diddy trial is in the books and while there was some more interesting tidbits from celebs, friends and staffers ... it feels like prosecutors are all over the map. Danity Kane singer Dawn Richard was first on the stand Monday and her testimony seemed to be…
... Read More
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Diddy's Former Assistant Testifies Cassie Told Him 'I Can't Get Out'

Published: 05/19/2025
One of Diddy's former assistants recalled a couple conversations he says he had with Cassie ... including one when he says Cassie told him why she couldn't leave Diddy. David James took the stand Monday in Diddy's federal trial and testified for the prosecution ... telling the jury he had been…
... Read More
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