“So Petty, I Love It”: 50 Cent Poses in ‘Free Diddy’ Shirts, Comments on Cassie’s Mother

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50 Cent took to Instagram to mock Sean “Diddy” Combs again amid the latter’s trial for s*x trafficking and racketeering.

The Candy Shop rapper shared an ironic AI-generated image of himself wearing a “Free Diddy” T-shirt following reports that individuals were being paid to stand outside the courtroom wearing similar shirts in support of the disgraced hip-hop mogul.

50 Cent, whose real name is Curtis James Jackson III, also referenced the testimony of Regina Ventura, Cassie Ventura’s mother, who accused Combs of threatening to release intimate videos of her daughter.

Jackson captioned the image: “He only made Cassie’s mom take out a home equity loan to pay 20k for him to not put out s*x tapes. Free itty bitty Diddy! LOL 😆 wait is that legal 😳”

50 Cent has trolled Sean “Diddy” Combs again, posting a photo that shows him in a “Free Diddy” T-shirt
50 Cent posing at event wearing a denim jacket and a black cap with a gold emblem, promoting Free Diddy shirts.

Image credits: Kevin Mazur/Getty Images

Trigger warning: this article contains details of exploitation, mistreatment, and physical violence that may be distressing to some.

He also mentioned reports that people were being paid $20 per hour to wear the “Free Diddy” shirts outside the Manhattan courtroom during the trial.

In a separate post, he wrote: “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!”

Jackson has trolled Combs on numerous occasions since the Big Boy Records founder’s September arrest.

50 Cent wearing a gray shirt posing at an event while making comments on Cassie's mother and wearing Free Diddy shirts.

Image credits: Paras Griffin/Getty Images

His feud with Combs dates back over a decade, when the 21 Questions rapper accused Combs of being involved in the 1997 crime of Notorious B.I.G. and criticized his alleged relationship with Daphne Joy, the mother of his second son.

Jackson has posted AI clips of Combs riding on the back of a motorcycle with Jeffrey Epstein, having baby oil in his jail cell, and an edited picture that depicts Jackson as every member of the jury in Combs’ trial.

Referencing the amount of baby oil allegedly used in “freak offs,” Jackson also posted an edited image of Combs’ yearbook in which he was voted “Most likely to get caught with 784 d*ldos and gallons of l*be.”

The rapper claimed Combs’ team was paying people $20 per hour to stand outside the courtroom and wear the T-shirts

 

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On Tuesday (May 20), Regina Ventura testified about her memories from the tumultuous decade during which Cassie was in an on-and-off relationship with Combs.

The mother claimed that in December 2011, Combs threatened her daughter via email after learning that she had started a relationship with rapper Scott Mescudi, known as Kid Cudi.

In the email in question, which was displayed in court, the incarcerated rapper threatened to release two intimate videos of Cassie, including one on Christmas Day, and said he would physically harm her and Mescudi.

50 Cent referenced the testimony of Cassie Ventura’s mother, Regina, who accused Combs of threatening to release intimate videos of her daughter

50 Cent wearing a Free Diddy shirt and New York Yankees cap in front of a classical building with columns.

Image credits: 50cent

50 Cent wearing Free Diddy shirts, posing and commenting on Cassie's mother in a playful, petty social media moment.

Image credits: 50cent

Regina told the court that the emails made her “physically sick.”

“I did not understand it, the s*x tape threw me. He was trying to hurt my daughter,” she said. “He wanted $20,000 because she was having a relationship with Scott Mescudi.”

Regina said she and Cassie’s father took a home equity loan, explaining, “That was the only way we could get the money.”

Asked why she had transferred the money to Combs, Regina said she was concerned about her daughter’s safety.

Regina said she took a home equity loan after Combs demanded $20,000

Man in light blue suit escorting woman in sunglasses and dark shawl, walking outdoors with people around in a city setting.

Image credits: John Lamparski/Getty Images

The $20,000 payment was eventually returned to the Venturas when Combs and Cassie resumed their relationship.

According to Regina, Combs demanded the payment because he was “angry” that Cassie was dating another man after he had spent money on her.

Cassie addressed the threats Combs allegedly made against her and Mescudi during her own testimony on May 14, telling the court that his comments led her to call off their relationship.

 

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“[There was] too much uncertainty if we continued to see each other,” she shared. “Sean said he was going to hurt the both of us.” 

Mescudi is expected to testify in the trial, prosecutor Maurene Comey said.

As per NBC News, Regina testified that she took pictures of her daughter’s injuries that month, which she claimed were caused by Combs.

“She was bruised and I wanted to make sure we memorialize it,” she explained.

The Candy Shop rapper has mocked Combs several times since his arrest last September

50 Cent posting a vintage photo of Sean Combs wearing a tuxedo, referencing Free Diddy shirts and Cassie's mother.

Image credits: 50cent

She also testified that Combs stole Cassie’s phone after the two had an argument during the time she visited her daughter in Los Angeles.

The defense had no cross-examination questions for Regina Ventura.

Cassie dated Combs between 2007 and 2018. In 2023, she filed a lawsuit against the rapper, claiming he had subjected her to a decade-long cycle of “violence and s*x trafficking.”

The lawsuit included accusations of r*pe in 2018 and multiple instances of domestic violence.

 

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Last year, Combs posted a video in which he admitted to beating his ex-girlfriend in a hotel hallway in 2016.

“It’s so difficult to reflect on the darkest times in your life, but sometimes you got to do that,” he said. 

“I went and I sought out professional help. I got into going to therapy, going to rehab. I had to ask God for his mercy and grace. I’m so sorry. But I’m committed to be a better man each and every day. I’m not asking for forgiveness. I’m truly sorry.”

His feud with Combs dates back over a decade, when he accused the jailed rapper of being involved in the 1997 crime of Notorious B.I.G

50 Cent wearing a black hoodie with a face print and a New York Yankees cap, posing indoors.

Image credits: thisis50

Cassie testified in court that Combs repeatedly forced her to engage with male commercial s*x workers for hours while they were dating, during what he called “freak offs,” which made her feel “disgusted” and “humiliated.”

The trial is expected to last about two months. Combs faces life in prison if convicted.

If you or someone you know is struggling with domestic violence, help is available. The Safe and Together Institute provides international resources.

“Don’t want to be on his bad side,” one reader quipped after the rapper’s latest post

50 Cent posing in a Free Diddy shirt while commenting on Cassie's mother in a casual social media post.

Screenshot of a social media comment mentioning 50 Cent, Diddy, and a playful remark about shopping and daddy.

Comment by Jonathan D Brown expressing amusement over Diddy and 50 Cent feud, referencing 50 Cent and Diddy online dispute.

50 Cent wearing Free Diddy shirt, posing outdoors and commenting on Cassie's mother in casual attire.

Comment from Jaime Dewey expressing love for 50 Cent's pettiness in response to Free Diddy shirts and Cassie's mother remarks.

Comment saying he’s so petty, I love it, featuring social media reactions related to 50 Cent and Free Diddy shirts.

50 Cent wearing a Free Diddy shirt and commenting on Cassie's mother in a social media post.

50 Cent wearing a Free Diddy shirt, posing and commenting on Cassie's mother in a casual setting.

Comment by Jacqueline Gampolo Gornitzky expressing admiration for 50 Cent and referencing his bold attitude.

Comment from Kato Hammond praising 50 Cent for not falling for Diddy's tactics in a social media post.

Screenshot of Facebook comment by Jeff Hall saying That man is a SAVAGE with laughing emojis under 50 Cent post

Comment from Fuchy Emodi laughing and stating 50 Cent drags to the gutters, reacting to Free Diddy shirts and Cassie's mother.

50 Cent wearing a Free Diddy shirt, posing and commenting on Cassie's mother, showing playful shade.

Comment from Tanya Whichard on 50 Cent's post wearing Free Diddy shirts, reacting to his remarks about Cassie's mother.

Comment on social media calling 50 Cent the most petty person on earth in discussion about Free Diddy shirts and Cassie's mother.

Comment from Tina Lawson reacting humorously to 50 Cent posing in Free Diddy shirts and mentioning Cassie's mother.

Comment from Novvon Griffin saying Karma going to get him in a Facebook-style chat bubble.

Screenshot of a social media comment stating 50 Cent has been calling out Diddy for years, highlighting petty drama.

Comment from Dustin Poe about 50 Cent's trolling, displayed in a social media style text with profile icon.

Comment from Kieti Francis saying He need his money by Monday with laughing emoji on social media post.

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