Donald Trump’s past admiration for Sean ‘P Diddy’ Combs has come back into the spotlight as the rapper faces serious charges of sex trafficking and racketeering. The 54-year-old music mogul was recently denied bail, prompting Jimmy Kimmel to reference the situation on his show, *Jimmy Kimmel Live*. Kimmel humorously remarked, “In the meantime, he’s getting his character references lined up,” before showing a clip from *The Celebrity Apprentice*.

In the footage, contestant Aubrey O’Day explained to Trump how her experience working for Diddy shaped her professional demeanor. She described herself as a “very strict and focused businesswoman,” crediting Diddy with instilling a sense of perfectionism in her work. Trump’s response, “Working for Diddy?” was met with Aubrey’s enthusiastic confirmation, “Absolutely.”

As the drama surrounding Diddy unfolds, the juxtaposition of Trump’s previous comments and the current allegations adds a layer of complexity to both figures’ legacies.

Trump gushed: “I love Diddy. You know he’s a good friend of mine, he’s a good guy.” He then asked: “Is he a good guy?” Aubrey looked awkward before replying: “I don’t want to answer that question.”

However, Trump continued praising Diddy as he said: “Oh well I think he’s a good guy, I’m gonna stick up for him.” After the clip, Jimmy joked: “To be fair he also thinks Kim Jong-Un is a good guy. Only the best people.”

Diddy was arrested at the Park Hyatt hotel in Manhattan, New York, on Monday evening. He has been charged with racketeering conspiracy, sex trafficking by force, fraud, or coercion, and transportation to engage in prostitution.

Diddy has pleaded not guilty, but was denied bail on Tuesday. He had a second bail application denied by a judge in a Manhattan courtroom on Wednesday. There is no suggestion Trump is in any way involved in the case.