Sean ‘Diddy’ Combs and Donald Trump’s Friendship Dates Back Decades as 30-Year-Old Photo Resurfaces

Hip-hop mogul Sean ‘Diddy’ Combs made plenty of friends throughout his high-paying career. However, most of them disappeared once Diddy was arrested in September 2024. He currently sits in jail on charges including sex trafficking and racketeering, and his trial is set to begin in May.

There are a bunch of people who have been spotted with Diddy at his parties over the last few decades, but it turns out he spent quite a bit of time with President Donald Trump. Photos of the duo go as far back as nearly three decades.

Sean ‘Diddy’ Combs has spent plenty of time with Donald Trump through the years

When Diddy was at the height of his fame in the early 2000s, he was regularly throwing massive parties. The mogul spent as much as $500,000 on each of these white parties, which saw guests dressed in all white — and a select few were invited to the “freak off” after parties, which is now where a bunch of the allegations against Diddy stem from.

But Diddy was always popping up at different events, and it turns out he and current President Donald Trump might have been pretty close. Back in 1997, Diddy and Trump were in the same suite watching the US Open together. Trump and his first wife, Ivana, sat in the suite alongside Diddy and his longtime then-girlfriend, Kim Porter. The photo, which is 28 years old, suggests the two were friends for nearly 30 years before Diddy’s arrest. That same month in 1997, Trump was photographed with Diddy and Clive Davis at the exclusive opening of Diddy’s New York City restaurant, Justin’s Restaurant.

Then, in 1998, Diddy and Trump once again spent time together at a polo match in the Hamptons, where the two posed for photos. Over the years, more and more photos were taken of Trump and Diddy posing at various events, including some alongside Trump’s wife, Melania Trump.

Donald Trump once praised Sean ‘Diddy’ Combs on the apprentice

Trump once publicized his friendship with Diddy during an episode of The Apprentice. “I love Diddy,” Trump can be seen saying in the resurfaced clip. “You know he’s a good friend of mine. He’s a good guy.”

The comments were from 2012 — 15 years after Trump and Diddy were first photographed together at the tennis match. “I think he’s a good guy; I’m going to stick up for him,” Trump also said in the clip after Aubrey O’Day, who previously worked with Diddy when she was a member of the band Danity Kane, didn’t want to say whether or not she thought Diddy was a good guy.

Kanye West recently called for Trump to pardon Diddy, though it doesn’t appear that Trump has acknowledged a potential pardon.