Inside Usher’s Relationship With Sean ‘Diddy’ Combs
Usher recently made headlines for his praise of Sean “Diddy” Combs. Many celebrities have tried to distance themselves from Combs since his arrest. While Usher has not condoned the behavior that landed Combs behind bars, he still speaks positively about him. Here is the history of Combs and Usher over the years.
Usher met Sean ‘Diddy’ Combs when he was 13
When Usher was 13 years old, he lived with Combs for roughly a year. The music mogul served as a mentor to him in the earliest days of his career.
“I got a chance to see some things,” Usher said on The Howard Stern Show (via People), adding, “I went there to see the lifestyle — and I saw it.”
He said Combs taught him how to navigate the music industry at an early age.
“I got a tutor, went to New York City, and he began to show me the ropes,” he said. “Some of the most valuable lessons I could ever learn as an entrepreneur were picked up when I spent that time in New York with him, this unwavering desire to create and make certain that your creative ideas executed.”
While he said he appreciated all that he learned while living with Combs, he said “Hell, no,” to letting his own children stay with Combs.
He said he picked up a habit from the disgraced mogul
Usher said he picked up habits from Combs that have helped him in his own career. He watched Combs work tirelessly, and he started to do the same thing. He claimed he doesn’t sleep “to this day.”
“I got it from him,” he said on an episode of OWN’s Oprah’s Masterclass (via The Mirror), adding, “I mean, this is a dude who just never slept. I mean, he’s probably the first one to get up and the last one to go to sleep, and that commitment I picked up.”
He once felt his mentor turned his back on him
While Usher generally has a positive view of Combs, he admitted he felt abandoned by him as a teenager. He asked Combs for money, and he refused.
“I looked up to Puffy, but he turned his back on me,” he said, per the Irish Examiner. “I went to him once when my record company wasn’t doing me so well, when I was about 17, and I’m like, ‘Yo, Puff, you know, I need some money, I don’t have any money, man, and can I borrow $5,000?’ And he’s like, ‘Nah, man, I haven’t got it.’ And yet he was walking Versace, you know?”
At one point, Combs was reportedly a billionaire. His net worth has seen a steep drop since his arrest.
Usher recently said he has no bad feelings about Sean ‘Diddy’ Combs
After Combs’ 2024 arrest, many of his celebrity friends have either disavowed him or refused to speak about their friendship. Usher said he still feels Combs made a positive impact on the world.
“I mean, this might be a bit controversial, but in the same way I think many people choose to look past the reality of what our country is, the standards that we now stand on, we can’t ignore the reality of the history,” he told Forbes. “In many ways, I think certain people are prosecuted and maybe not recognized for the greatness that they offer. I don’t have anything negative to say about Sean Combs because my experience was not what the world has seen and how he’s been misrepresented.”
While he didn’t defend the actions that led to Combs’ prison sentence, he said he felt people shouldn’t ignore his impact.
“I’m not saying that every man is perfect,” he said. “I’m not saying that all of us don’t have flaws. But I can’t with any sense of humanity not recognize the valuable contributions that this man made for us as Black entrepreneurs, for us as businessmen, for us as people who have transitioned culture and ideas into something that’s tangible.”
