Watch Trump stand up for 'good guy' Diddy in old 'Apprentice' clip after Aubrey O'Day suggests otherwise

LOS ANGELES, CALIFORNIA: Late-night host Jimmy Kimmel brought the heat during his monologue on 'Jimmy Kimmel Live!' on Wednesday, September 18. The target of his jokes? None other than former president Donald Trump and embattled music mogul Sean “Diddy” Combs.

Kimmel took a trip down memory lane. He pulled up an old video of Trump defending Diddy even though Aubrey O’Day, one of his 'Celebrity Apprentice' contestants, didn’t seem to agree with his glowing review.

A flashback to Donald Trump defending Diddy

Jimmy Kimmel started off by joking, “This was definitely not the morning that you wanted to wake up feeling like P Diddy.” He then dove into the mounting legal troubles surrounding the once-beloved music mogul, who’s now facing a slew of sex crime charges.

Kimmel ran through the allegations against Diddy before highlighting the fact that the former rapper is stuck behind bars, being denied bail after being labeled a flight risk. 

But the real punchline came when Kimmel aired a blast from the past—an old clip from 'Celebrity Apprentice'. In the video, Aubrey O’Day — the former singer from Danity Kane — is seen trying to pitch herself to Trump. O’Day credits her perfectionism to her time “working for Diddy.”

“Working for Diddy? I love Diddy,” Trump said. “You know he’s a good friend of mine, he’s a good guy. Is he a good guy?” When O’Day hesitates and awkwardly dodges the question, Trump defends Diddy, “Well, I think he’s a good guy. I’m going to stick up for him.”

Back in the studio, Kimmel couldn’t resist throwing a zinger, “To be fair, he also thinks Kim Jong Un is a good guy, so only the best people!”

According to The Wrap, the late-night comedian also went on to poke fun at some of the more eyebrow-raising details surrounding the case. Among the revelations? Authorities reportedly found over 1,000 bottles of lubricant at Diddy’s properties—fuel for more jokes, of course.

Kimmel quipped, “More than 1,000 bottles of lubricant? They won’t be able to keep him behind bars, he’s going to slip right out!” He then added with a smirk, “I mean, what a trip to CVS that is.”

Meanwhile, Aubrey O’Day took to X (formerly Twitter) on Monday following Diddy’s arrest. “The purpose of Justice is to provide an ending and allow us the space to create a new chapter,” she wrote. “Women never get this. I feel validated. Today is a win for women all over the world, not just me. Things are finally changing.”

Donald Trump faces backlash for defending Diddy in resurfaced clip

Critics of Donald Trump took to social media to slam him for praising Diddy in the recently resurfaced video clip.

"Birds of a feather," one social media user posted on X.

"Of course, he would stand up for him," another wrote.

"Why does this conversation even exist?" someone else asked.

"This f---ing trash right here is a huge part of why we are where we are right now," read one comment.

"I'm not even surprised," another user offered.

Jimmy Kimmel sang a different tune in 2018

A clip from an August 1, 2018, episode of 'Jimmy Kimmel Live!' resurfaced, showing a completely different vibe from the show's anchor. Back then, Diddy wasn’t caught up in legal troubles and so Kimmel had no problem joking about how the rapper would make a better president than Trump.

During that episode, Kimmel asked Diddy if he’d ever consider running for president while playfully comparing his failed vodka brand to Trump’s.

“By the way, President Trump had his own vodka, it didn’t work out anywhere near as good as yours. Maybe you could be president. Do you ever think about anything like that?” Kimmel asked.

Diddy replied, “I wouldn’t make a good president. I wouldn’t really pass any of the things that you have to pass. But I guess Trump did it.”

Kimmel responded, “You would be a Boy Scout by comparison.” Diddy joked back, “Yeah... Nah, I like what I’m doing.”

The audience ate it up, laughing along with the banter. At one point, Kimmel even said, “You know what, I think that at this point? Almost anybody would be doing a better job” — a jab directed at Trump, of course.

Diddy then turned the tables, asking if Kimmel would ever run for president. “I wouldn’t do a better job,” Kimmel joked, offering to be Diddy’s running mate instead. “I say that because I know you won’t [run],” he quipped.

Diddy’s legal troubles

On Monday, Diddy was arrested following raids on his homes in Los Angeles and Miami. The raids were connected to a federal human trafficking investigation, and things aren’t looking good for the former music mogul. He appeared in Manhattan federal court just days later, where he pleaded not guilty to multiple charges.

If convicted, Diddy faces serious time—potentially 15 years behind bars, or even life.

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