Diddy made 'stupid and arrogant' mistake ahead of sentencing, says OJ Simpson lawyer

Sean "Diddy" Combs was once one of the world's most popular entertainers, but his courtroom performance left little to be desired, according to experts.

The fallen rap mogul was sentenced to 50 months in prison on federal prostitution charges. Judge Arun Subramanian also requested the court impose five years of supervised release and for Diddy to pay a $500,000 fine.

Prior to receiving his sentence, the court heard from prosecutors that Diddy was already making immediate plans for a public speaking engagement in another state.

Diddy's interest in pursuing business outside the case – and ahead of his sentencing – was a "slap in the face," according to Harvard Law professor and OJ Simpson attorney Alan Dershowitz.

DIDDY SENTENCED TO OVER 4 YEARS IN PRISON FOR FELONY CONVICTION
 

"I can't imagine anything more stupid than that," Dershowitz exclusively told Fox News Digital. "How anybody permitted him to do that … It's just a slap in the face to the judge. It's outrageous. I can't imagine any lawyer or any responsible person allowing … I would have quit the case."

"If I had been Diddy's lawyer and Diddy had said, 'I'm gonna make an arrangement, and I'm going to make it public.' I would've said, 'Yeah, and you're going to get a new lawyer. I'm not representing somebody who is so stupid and arrogant.'" 

He added, "I mean, I'm not Dr. Kevorkian. I don't believe in walking my clients into a death chamber. And that was a kiss of death."

Diddy's eight-week trial – where jurors heard dozens of witness testimonies – concluded July 2. On sentencing day, the court received an 11-minute video featuring clips of the rapper with his kids when they were young, as well as current videos where his children professed their love for their father.

They praised their "inspiring" father for his unwavering support. The video also attempted to emphasize Diddy's charitable contributions, which were mentioned by his defense during the hearing, throughout his life before his arrest in 2024.

Diddy cried as the 11-minute clip featuring home video of his family played in the courtroom. Robert Shapiro, Partner of Glaser Weil and OJ Simpson's lawyer, told Fox News Digital that family testimony would be "extremely emotional," but anything provided to the court would also give room for judgment.
 

"I would imagine there are many things that he has done that are positive," Shapiro said. "But he's got one big negative – that 11-minute video. Disappears with a 30-second video. And so a judge is weighing that and the guidelines specifically allow for conduct not considered in the guidelines."

The 55-year-old rapper was nearly void of reaction throughout his sentencing hearing, but was overcome with emotion as his kids addressed the court. He then thanked the judge for giving him "a chance to speak" for himself as he spoke out for the first time.

DIDDY CRAFTS IMAGE OF MODEL PRISONER AMID FEARS OF RETALIATION FROM VICTIMS

"One of the hardest things has been to be quiet, not being able to express how sorry I am for my actions," Diddy said. "I want to apologize again to Cassie Ventura for any harm I caused emotionally or physically. I don't take that lightly."

Diddy also apologized to Jane, who testified under a pseudonym during the trial. The rapper said, "I didn’t mean to hurt you. Sorry that I brought you into my mess." Diddy also apologized to all victims of domestic violence.

The producer admitted his "actions were sick," as he referenced substance abuse issues. "I was out of control. I needed help, but I didn’t get the help," he said. "I can make no excuse because I knew better. My mama taught me better. My faith taught me better."

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He continued, "Because of my decisions I lost my freedom. I lost the opportunity to effectively raise my children and be there for my mother. I lost all my businesses I lost my career. I totally lost my reputation. I lost my self respect. 

"I’ve been humbled and broken to my core. I hate myself right now. Stripped down to nothing. I really am truly sorry for it all no matter what they say. I want to apologize to my seven children." 

Shapiro noted that the judge likely walked into the courtroom knowing how he was going to sentence the Bad Boy Records founder. 
 

"My experience is that judges in advance have a pretty good idea of what the sentence is, and they're not going to be swayed tremendously," Shapiro said. 

"Something may come up, but generally a judge has spent a lot of time, has read all the letters, has read the probation department recommendations, has submitted and read the briefs that were submitted by the lawyers, and pretty much knows and has an outline of what he or she is going to say. 

"And his were simple – What you did and your conduct, and that was the key word, substantial sentence for your conduct, not for your crime." 

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While Diddy received his sentence Friday for two charges of transportation to engage in prostitution, former federal prosecutor Neama Rahmini told Fox News Digital that Diddy's legal team will likely still pursue an appeal.

"This isn’t the end of the legal road for Diddy, though," Rahmani said. "He can and will appeal, and he has arguments that the judge improperly calculated the guidelines and considered acquitted conduct."
 

"And of course, Diddy’s best chance of freedom has always been a presidential pardon," Rahmani noted.

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Rahmani added, "Expect a strong lobbying effort by Diddy’s team in the coming days and weeks. This story is far from over."

Days before Diddy was set to appear in court for his sentencing, Judge Subramanian rejected the rapper's last-ditch request for a new trial and demand for a full acquittal. The federal judge said the prosecution provided "overwhelming evidence" of Diddy's guilt on the charges of transportation to engage in prostitution.

Tracy Wright is an entertainment reporter for Fox News Digital. Send story tips to Tracy.Wright@fox.com.