“I think I was sabotaging myself” — TK Kirkland opens up to Shannon Sharpe about robbing Diddy in the 90s 

In a recent installment of the Club Shay Shay podcast, stand-up comedian TK Kirkland opened up about getting in legal trouble for robbing rapper Sean "Diddy" Combs in 1998.

During the podcast uploaded on July 2, 2025, TK Kirkland recounted how the judge named Margret, who was presiding over the case, wasn't lenient with him. Instead, she was more focused on how he had managed to avoid the consequences for his past actions.

"You know, when you look at somebody's record, she's [Judge Margret] seeing like I should have been locked up years ago, right? How did he get to me? That mean somebody wasn't doing their job. And I could tell she was not playing," TK added.

Looking back at his arrest, TK expressed that despite having money, he was doing "dumb stuff" and acted recklessly. He now looks back at that time and views it as "self-sabotage."

"I was just doing dumb stuff. I was rich, but I was doing stupid stuff. So, basically, what I see now, I don't think I wanted success. I think I was sabotaging myself. That's the only way I could look at it. I didn't want that. I was rich, but for some reason I didn't want to be richer," TK stated.

Talking about his arrest for robbing Sean Combs, Kirkland claimed that despite having a surrender date, he delayed turning himself in for three months. He stated that by that time, the FBI had begun to find him. However, he added that when he finally surrendered, he was bailed out within hours.

Kirkland explained that he fought the case for a while before ultimately preparing to accept a plea deal, as he had a predicate felony in his record. This meant he had to serve mandatory prison time, typically four to six years, with no room for negotiation.

"Predicate felony is you caught a felony within a year," he added.

He eventually hired lawyers to represent him in court. However, he was sent to Rikers Island Jail for only 30 days because he took his plea deal off the table.

"So, I'm in there for 30 days because I took my deal off the table, cuz I took a deal. I was going to do four to six. I was going to turn myself in, but when I came to court, I took the deal off the table."

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TK Kirkland recalls nearly testifying against Diddy in 1999 shooting case

New York Mayor Eric Adams (R) presents Sean "Diddy" Combs with the keys to the city in Times Square (Image via Getty)

Elsewhere in the podcast, TK Kirkland claimed that during his time serving in Rikers Island Jail in 1999, Diddy was involved in a gunfight incident that left three people injured.

According to New York Magazine, for the unversed, in 1999, Diddy and his then-girlfriend Jennifer Lopez had been at Club New York in Manhattan, celebrating the upcoming release of an album by Shyne, also known as Jamal Barrow. Shyne was Diddy’s 21-year-old protégé. During the celebration, gunshots broke out during a fight, leaving three injured.

Per Forbes, Lopez and Combs eventually fled the scene but were caught by police after running a red light. Police discovered a gun in their car, and Diddy was charged with gun possession and attempting to bribe the driver to claim the weapon. However, he was cleared of all the charges.

TK claimed that while he was serving in Rikers Island Jail, authorities came up to him to testify against Sean Combs and falsely say that he had seen him with a gun. He admitted to briefly considering the offer.

"So my attorney is like, TK, you want to help out the prosecution? Me being smart, I said, 'Tell them to get me out of here. We could talk about it.'"

He alleged that authorities took him to Club New York, the site of the shooting, and attempted to set him up as a witness. However, he added that after three days, he declined to testify.

"And they want me to testify in the grand jury against Puff. And I looked at my attorneys and I said, 'No, I tell them I'm okay. I'm all right.' Then quit them," TK added.

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In other news, after an intense seven-week-long s*x trafficking and racketeering conspiracy trial, Sean "Diddy" Combs has been cleared by the jury of racketeering conspiracy and sex trafficking charges. However, he was found guilty of two counts of transportation to engage in prostitution, per CNN.