Yes, they were friends for many years, though as the president noted while talking to reporters in the Oval Office, it seems Combs soured on Trump once he entered politics.
Its unclear if Trump and Diddy were bosom buddies, or just “friends” in the sense that they were two reality-TV celebrities who ran in the same circles in the late ’90s and early ’00s. But we do know that they publicly discussed their friendship on several occasions, praised each other’s business skills, and were photographed together at many events.
A 1999 Vibe piece written by Nancy Jo Sales about Trump’s relationship with the hip-hop community noted that he was the first to show up to Diddy’s birthday party, and that then-17-year-old Ivanka was impressed that her dad knew such a cool celebrity. “I think Puff Daddy is a great guy,” Trump said.
During a 2012 episode of The Celebrity Apprentice, Trump told contestant Aubry O’Day, who had worked for Diddy, that he was a friend.
“I love Diddy. You know he’s a good friend of mine, he’s a good guy,” Trump said. He then asked O’Day, “Is he a good guy?” and she said she didn’t want to answer. (Years later, the singer accused Diddy of “grooming” and said she was kicked out of the girl group he created, Danity Kane, for not doing “what was expected” of her — “not talent wise but in other areas.”)
“I think he’s a good guy, I’m going to stick up for him,” Trump said.
Diddy referred to Trump in his 2006 hit “We Gon’ Make It,” rapping, “I spend absurd money, private bird money / That Bill Gates, Donald Trump, Bloomberg money (you know what it is).”
In 2015, months after Trump launched his presidential campaign, Diddy told the Washington Post, “Donald Trump is a friend of mine, and he works very hard.”
