Prosecuted Pals? Donald Trump Once Called Diddy a "Good Friend" and "Good Guy"

When you're former President Donald Trump, the people you call "friends" are scrutinized by everyone. And this week, that scrutiny falls on a friendship the former President may wish he never had with rapper Sean Diddy Combs. Diddy was arrested in September 2024 on sex trafficking and racketeering charges, making him someone most people would want to distance themselves from. But several years ago, Trump once called Diddy a "good friend" and a "good guy."

It's another blow to Trump's reputation just when he's hoping to rid himself of any image that he's connected to crimes. With the 2024 Election just months away, he really can't afford yet another blemish on his name. Here's what Trump said about Diddy back in the day, and why it matters.

On Sept. 16, 2024, rapper Sean Diddy Combs was arrested on federal sex trafficking and racketeering charges, after months of civil lawsuits which accused the former superstar of sex trafficking, sexual abuse, and rape. A 14-page indictment paints a grim picture of a person whose power and fame gave him access to his alleged victims.

Trump, who has himself faced multiple civil lawsuits accusing him of sexual misconduct, is hot on the trail to Election Day 2024, and can't afford for any blemishes on his image or distractions in a vital time for his campaign. Yet comedian Jimmy Kimmel isn't letting him walk away from his own words, which have come back to haunt the former President and former reality TV star.

Jimmy pointed out on Jimmy Kimmel Live that Trump once had praise for the rapper. On Trump's hit show The Celebrity Apprentice, he was speaking with then-contestant Aubrey O'Day. In her interview with Trump, Aubrey suggested that she was a bit of a perfectionist due to working for Diddy for six years. The former President's interest was piqued, and he asked, "Working for Diddy?"

Aubrey responded, “Absolutely." Trump then praised Diddy, saying, "I love Diddy. You know he's a good friend of mine, he's a good guy. Is he a good guy?" Aubrey declined to answer that question, to which Trump responded, "Oh well I think he's a good guy, I'm gonna stick up for him." On Kimmel, Jimmy had a quip ready and ended the bit by joking, “To be fair, he also thinks Kim Jong-Un is a good guy. Only the best people.”

For most people, being friends with one bad apple wouldn't necessarily paint them in an unflattering light. After all, we never really know what people are doing behind closed doors. But Donald Trump has something of a problem with his friends: They just keep getting arrested. And on sexual misconduct-related charges, too.

Case in point: Jeffrey Epstein. The former President has tried to distance himself from the infamous sex trafficker and pedophile, but pictures of the pair partying together in the past have continued to haunt Trump's steps even long after Epstein's death in prison.

Right now, Trump is trying to separate his image from private citizen Trump and re-cast himself as a president, which means he needs as little attention on past personal relationships as possible.