Resurfaced Clip Of Trump Praising Diddy Has The Internet Unsurprised: 'There Is Always A Video'

Donald Trump may not be one of the celebs taking the stand during Sean "Diddy" Combs' sex-trafficking and racketeering trial, but that doesn't mean he wasn't a friend of the disgraced star. An unearthed clip from Trump's pre-politics gig, "The Apprentice," is putting a spotlight on his feelings about Diddy. And, as one person commented on the clip on X, formerly known as Twitter, "There is always a video, isn't there?"

Flashback: Trump asked a woman who worked for Diddy if he's a "good guy." The woman refused to answer.

Trump: "I think he's a good guy. I'm gonna stick up for him." pic.twitter.com/vLMzFdk2hD

— Republicans against Trump (@RpsAgainstTrump) June 4, 2025

In 2005, Diddy created the pop group Danity Kane on MTV's reality series "Making the Band." According to group member Aubrey O'Day during a 2022 "Call Her Daddy" interview, Diddy reportedly fired her when she refused his orders — orders she described as "non-talent-wise, in other areas." Back in 2012, O'Day appeared on the fifth season of Trump's "Celebrity Apprentice." In a resurfaced clip from the season, O'Day tells Trump, "... Working for Diddy for six years trained me to have to be perfect," per X. Trump interrupted her, asking, "Working for Diddy?" He quickly added, "I love Diddy." As horrific details about Diddy's alleged past behavior pile up amidst his trial, "I love Diddy" is not something you want to be saying in a clip circulating online. Yet, Trump took it a step further, adding, "... He's a good friend of mine; he's a good guy." So, about a decade ago, Trump considered Diddy to be a good friend. It's worth noting that this was right in the middle of the timeline of Diddy's alleged crimes.

It is certainly not a good look for Donald Trump to be such a Diddy fan, but the turn the conversation took next was even more telling. Immediately after describing Diddy as a "good guy," he asked Aubrey O'Day, "Is he a good guy?" Trump's fixation on whether or not Diddy is a good person seems peculiar if he does, in fact, think of him as a good person. Repeatedly bringing it up and asking about it implies that he knows that this isn't necessarily true. "I don't want to answer that question..." O'Day responded. Trump quickly doubled down on his own opinion, saying, "Well, I think he's a good guy. I'm gonna stick up for him."

This exchange could have been Trump subtly acknowledging Diddy's sordid behavior. However, he is doing so while repeatedly complimenting Diddy. The resurfaced clip may feel surprising, but it really shouldn't. Trump's name appearing on the Epstein list wasn't surprising given the pair's long history; in a recording, Jeffrey Epstein reportedly said, "I was Donald's closest friend for 10 years," per the Daily Beast. And, surely, we all remember the things Trump said in the infamous "Access Hollywood" leaked tape scandal. With all of that in mind, it doesn't seem so surprising that Trump thought of Diddy as a "good friend" who he "loved." In fact, it even suggests that Diddy's potential Trump pardon might not be a pipe dream after all.