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50 Cent Posts AI Picture of Himself Wearing ‘Free Diddy’ Shirt

todayMay 20, 2025

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50 Cent is back at it.

The Queens rapper and filmmaker continues to troll Diddy as the Harlem mogul’s sex trafficking trial heads into its second week. This time, he posted an AI-generated picture of himself on Instagram wearing a white “Free Diddy” shirt in front of a courthouse and followed that up with a screenshot of an article referencing testimony from Cassie‘s mother, Regina Ventura, in which she testified that Diddy requested $20,000 that he spent on her daughter after he found out she was dating Kid Cudi, forcing Cassie’s parents to take out a loan.

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“He only made Cassie’s mom take out a home equity loan to pay 20k for him to not put out sex tapes,” 50 wrote in the caption. “Free itty bitty Diddy! LOL wait is that legal.”

Just over the weekend, 50 Cent joked about people being offered $20 an hour to wear “Free Diddy” shirts in front of Manhattan federal court, writing, “Diddy paying people to wear Free Diddy shirts is diabolical, but $20 a hour ain’t bad. I might go throw that on for a hour tomorrow.”

In another picture he posted, this time wearing a black “Free Diddy” shirt, his caption read: “Ok now where do I send my $20 invoice guys, a deals a deal. If you want I can be there tomorrow from 3 to 4 OK!”

In other Diddy trial news, Kid Cudi is expected to testify sometime this week, according to prosecutors. And it’s pretty safe to assume that the subject of Diddy allegedly blowing up Cudi’s car over his relationship with Cassie will be broached.

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