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Ashton Kutcher and Sean Combs attend WeWork Presents Second Annual Creator Global Finals at Microsoft Theater on January 9, 2019 in Los Angeles, California© Getty

From Ashton Kutcher to Cuba Gooding Jr: who's in Sean 'Diddy' Combs' inner circle?

Since the the music mogul's homes were raided by Homeland Security, some of his friends' past comments insinuating suspicious behavior have resurfaced

Beatriz Colon
Beatriz Colon - New York
New York WriterNew York
April 3, 2024
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Sean "Diddy" Combs has been under intense scrutiny – not just from paparazzi but also from Homeland Security – ever since the latter carried out a raid in his homes in Los Angeles and Miami as part of a federal investigation led by the Southern District of New York into alleged human trafficking.

The shocking development comes shortly after the music mogul's former producer Rodney "Lil Rod" Jones filed  federal lawsuit against him, not only accusing him of sexually harassing and drugging him, but he also claimed the Bad Boy Records founder engaged in more illegal activity that includes drug and sex trafficking as well as soliciting sex workers, among other allegations.

Also with close eyes on them, whether from Homeland or just netizens, are those in Diddy's inner circle, as well as those who were name dropped in Lil Rod's complaint. Below, catch up on just who some of those friends are.

Cuba Gooding, Jr. and Sean P. Diddy Combs during Loon's Self-Titled Debut Album Release Party at Show in New York City, New York - 2003© Getty
Cuba and Diddy at a party in 2003

Cuba Gooding Jr.

In Lil Rod's complaint, he claimed Diddy allegedly groomed him to "pass him off" to his friends, one of which was the Jerry Maguire actor.

He further claimed that he was introduced to Cuba while they were all vacationing in the Virgin Islands on Diddy's yacht in January of last year, and that he had to forcibly reject several sexual advances from Cuba.

Ashton Kutcher, Demi Moore and Sean "Diddy" Combs arrive to the White Party to benefit Malaria No More held at a private residence on July 4, 2009 in Beverly Hills, California© Getty
Ashton and Diddy, pictured above with Demi Moore in 2009, have been friends for over 20 years

Ashton Kutcher

Ashton isn't one of the people mentioned in the lawsuit, though he does have a decades long friendship with Diddy. 

During an appearance on Hot Ones in 2019, the That 70s Show alum said he and Diddy became "fast friends" in the early 2000s as he recalled: "It started over Punk'd cause he's like, 'Yo, you can't punk me.' I was like, 'I don't know what to tell you, everybody's on the table.' So, that started our conversation."

MORE: Sean 'Diddy' Combs' son King shows off lavish 26th birthday celebrations one week after home raids

The two both had shows on MTV at the time (Ashton Punk'd and Diddy Making the Band), and ran the New York City Marathon together in 2003. Since the latter's several sexual assault allegations have come to light, Ashton's comment on Hot Ones "I've got a lot I can't tell" about Diddy's infamous parties has resurfaced.

WATCH: Usher reveals 'wild' things that happened at Sean 'Diddy' Combs' home when he lived there as a teen

Usher

Another one of Diddy's friends whose comments, suspicious in hindsight, have resurfaced is that of Usher's, who lived at Diddy's home when he was 14 years old back in 1994.

MORE: Sean 'Diddy' Combs' $40M Los Angeles home becomes tourist destination after raid – see photos

During a 2016 interview on The Howard Stern Show, the "Hey Daddy" singer said: "I got a chance to see some things. I don't know if I could indulge and even understand what I was looking at," adding: "It was pretty wild. There were very curious things taking place and I didn't necessarily understand it."

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