Inside Kanye West’s Longtime Friendship — and Feud — With Sean ‘Diddy’ Combs
Kanye West and Sean ‘Diddy’ Combs are two of the most controversial people in the hip-hop industry. Both men have effectively been canceled, though West still pops up at plenty of events (including alongside his naked wife, Bianca Censori, at the 2025 Grammy Awards).
West drew attention to himself in 2022 when he made antisemitic comments on social media, and Diddy was arrested in September 2024 on charges including sex trafficking and racketeering. But after West called for Diddy to be “free” in early February 2025, we’re taking a closer look at the rappers’ friendship – and feud.
Kanye West and Sean ‘Diddy’ Combs have a complicated friendship
West and Diddy were both in the hip-hop industry for decades, so it’s no surprise they crossed paths plenty of times. But over the years, people have seen glimpses of how close the two were.
“The other night I go to the Kanye West concert, and I’m going there to see Kanye do this thing. I don’t have anything but high expectations; the concert changed my life,” Diddy said, explaining how West made him feel more inspired about the hip-hop industry, per Mirror.
In 2022, West presented Diddy with the Lifetime Achievement Award at the BET Awards. “You see I’m saying favorite artist — everything, not specifically production, the trip. Back then there was so many rules to hip-hop, and he broke all of them,” West said while praising Diddy. He even hinted that Diddy inspired him to pursue a marriage to Kim Kardashian. The two reportedly also spent time mentoring Justin Bieber earlier in his career, though that has come under fire since the Diddy allegations have come to light.
However, things went south between the two after West produced “white lives matter” t-shirts, which were not well-received by Diddy. He said the move was “tone deaf,” and he and West had a private, heated conversation that West eventually made public on social media. Since then, the two had not been spotted together much.
Kanye West just said that Sean ‘Diddy’ Combs should be ‘free’
West is no stranger to controversy. In early February, he and his wife, Bianca Censori, shocked the Grammy Awards red carpet when Censori discarded her jacket and walked the carpet nearly naked, with West at her side. The move was seen as distasteful, but West didn’t stop there.
Shortly after the incident, West took to X to say that Diddy should be “free” from jail. “FREE PUFF,” West wrote on X. He then followed it up with a tweet directed at Donald Trump, tagging him on the app and writing, “PLEASE FREE MY BROTHER PUFF.” He likened the situation to Chris Brown, suggesting he and Brown have a longtime friendship. West then went on another antisemitic rant.
West’s controversial tweets have landed him in hot water in the past, and this time seems no different. Evidently, he’s proven that he believes his friendship with Diddy is long-lasting.
