Jimmy Kimmel Mocks Donald Trump For Once Deeming 'Friend' Sean Diddy Combs a 'Good Guy'

Federal officials detained Sean Diddy Combs in New York, on Monday, over charges of sex trafficking, racketeering conspiracy, and transportation to engage in prostitution. The rapper pled not guilty. On Tuesday, he was ordered held without denied bail. Referencing the case, late-night host Jimmy Kimmel mocked Comb's connection with former president Donald Trump. “In the meantime, he’s getting his character references lined up," Kimmel quipped, playing an old clip from The Celebrity Apprentice, that featured Trump praising the rapper and deeming him a 'good guy.' 

According to The Independent, in the resurfaced clip then-contestant Aubrey O’Day, explained to the billionaire business mogul that she was “a very strict and focused businesswoman because working for Diddy for six years trained [her] to have to be perfect.” “Working for Diddy?” Trump interrupted. “Absolutely,” O’Day said. “I love Diddy. You know he’s a good friend of mine, he’s a good guy,” Trump responded. “Is he a good guy?” he asked. Oddly, O'Day glanced sideways for a while, before answering, “I don’t want to answer that question.” “Oh well I think he’s a good guy, I’m gonna stick up for him,” Trump had stressed. “To be fair he also thinks Kim Jong-Un is a good guy,” Kimmel mocked, adding, “Only the best people.” 

Singer O'Day, who had been a part of Diddy's Danity Kane girl group, appeared in the fifth season of the reality show, in 2012, for 14 weeks, before being sacked. She stated, during her 2022 Call Her Daddy podcast appearance, that she was expelled from the girl group in 2008 for not complying with the music mogul's requirements for non-musical content. She is currently one of many individuals who have sued the musician in civil court.

In a post on X, on Tuesday, the former girl group member stated that she feels 'validated' by the Last Night rapper's imprisonment. “The purpose of Justice is to provide an ending and allow us the space to create a new chapter. Women never get this. I feel validated. Today is a win for women all over the world, not just me. Things are finally changing." O'Day told People magazine in June that she didn't "feel vindicated at all" by Combs's claims. "There's no vindication when you're a victim of someone... Anyone being exposed, or any truths being told, don't change the reality of what you experienced," she said.

She added, "It's a forever thing that you have to wake up every day and choose to evolve past. It doesn't go away. It's like childhood trauma. We don't like to think it just disappears in our thirties, but really we start realizing how bad it really is in our thirties." In an October 2015 interview with The Washington Post, when Trump was a longshot in the 2016 Republican presidential primaries, Combs had talked about his affinity with him. "Donald Trump is a friend of mine, and he works very hard," he said.