Sean 'Diddy' Combs is not the only 'bad boy' as high-stakes crime drama plays out (2024)

The saga continues as Sean "Diddy" Combs, the 54-year-old hip-hop and media mogul who saw two of his mansions raided by Homeland Security Investigations and local police last month, is not the only high-profile figure haunted by encounters with law enforcement linked to a series of new lawsuits alleging sex trafficking and assault.

A number of prominent figures on different sides of the case have had run-ins with law enforcement, either as witnesses, suspects or victims.

Actor Ashton Kutcher was the witness in the murder trial of a serial killer. Combs' father was gunned down in his car. And actor Cuba Gooding Jr., a co-defendant in one of the lawsuits against the Bad Boy Records founder, recently took a plea deal in an unrelated criminal case.

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Sean "Diddy" Combs sits outside his Star Island home in Miami Beach, Florida, on April 6, 2024. (Zak Bennett for Fox News Digital)

Music producer Lil Rod, whose real name is Rodney Jones, alleges that there are "HUNDREDS of hours of footage and audio recordings of Mr. Combs, his staff, and his guests engaging in serious illegal activity."

Legal experts have told Fox News Digital that if the alleged tapes exist, investigators will be scouring through them after serving the search warrants to see if any crimes have been committed – and what other high-profile figures may have been present.

"You got to get the videotapes and look at them for all the people that were in that house or that he had dealt [with], whether it be politicians, big people with money, celebrities, criminals – they want to see everything in there," said Derrick Parker, who was part of the NYPD's rap-industry intelligence unit.

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Sean "Diddy" Combs is shown outside his Star Island home while chatting with his mother, Janice Combs, in Miami Beach, Florida, on April 7, 2024. (Zak Bennett for Fox News Digital)

Whether or not that turns out to be the case, a number of people whose names have already come up have been embroiled in tragedies. Combs has denied all the allegations against him in all the civil lawsuits.

Combs' father, Melvin Earl Combs, died in an ambush shooting when the future mogul was 3 years old.

His father was a drug dealer with ties to former kingpin Frank Lucas, who Denzel Washington portrayed in the 2007 movie, "American Gangster." Combs has said his father's violent death was a lesson that inspired him to focus on finding success through legitimate business.

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Actor Cuba Gooding Jr. appears in court on Jan. 22, 2020, in New York. (Alec Tabak/The Daily News via AP)

The movie also featured appearances by Gooding, who is named a co-defendant in a sex assault lawsuit against Combs, and the rapper, actor and reality star T.I.

Gooding took a plea deal in 2022, avoiding jail time and a criminal record after kissing a woman against her will at a nightclub.

T.I. has one of Bad Boy's lawyers, Shawn Holley, representing him in a case filed by the same lawyer who filed the lawsuit against Combs and Gooding, Tyrone Blackburn. Holley is a high-powered defense attorney, part of the "Dream Team" that represented O.J. Simpson in the mid-1990s.

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Tameka "Tiny" Harris and T.I. attend Jay "Jeezy" Jenkins' 2nd annual Sno Ball Gala at Flourish Atlanta on Sept. 29, 2022, in Atlanta. (Derek White/Getty Images)

Her long list of celebrity clients has included Tupac Shakur, Snoop Dogg and Danny Masterson. And she is currently defense counsel in a Jane Doe lawsuit accusing Combs of trafficking an 11th-grader from Detroit to New York City.

Even people further removed from the case have bizarre connections to the entertainment underworld.

Danny Masterson and wife Bijou Phillips are photographed outside court in May 2023. (Myung J. Chun/Los Angeles Times via Getty Images)

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Al B. Sure!, the artist who recently insinuated his 2022 health issues may have some tie to Combs, has a spokesperson whose son was cleared of manslaughter in New York City in 2016.

Khari Noerdlinger, whose mother worked for the wife of New York City Mayor Bill de Blasio at the time, had high-powered defense lawyer Jeff Lichtman. His clients have included John Gotti Jr., cartel lord Joaquin "El Chapo" Guzman, and now Combs' son, Justin Combs.

Sean "Diddy" Combs and son Justin attend "The Love Album" listening party on Sept. 15, 2023, in New York City. (Johnny Nunez/WireImage)

Stevie J, a Grammy-winning music producer and close Combs friend who has been photographed at the mogul's Miami mansion multiple times in recent days, is represented by Lizzie Grubman, a former publicist for Jay-Z who spent more than a month in jail after backing her Mercedes SUV into a crowd of people at a Hamptons nightclub in 2002.

Stevie J is seen outside of Sean "Diddy" Combs' home in Miami Beach, Florida, on April 3, 2024. (Mega for Fox News Digital)

Kutcher, who reportedly said he expects to be subpoenaed in connection with a federal investigation into Combs, had a friend who was murdered by serial killer Michael Gargiulo, the "Hollywood Ripper," in 2001.

The star is also a friend and former castmate of Holley's former client, Masterson, who is serving 30 years to life in prison for rape.

Ashton Kutcher said he formed a fast friendship with Sean "Diddy" Combs. (Getty Images/File)

Combs, a billionaire who branched out of hip-hop into fashion, liquor, television and even acting, had a series of violent incidents coinciding with his rise to fame, beginning with a deadly crowd stampede at a 1991 benefit event. Through much of the decade, he was a central figure in the deadly feud between East Coast and West Coast hip-hop stars. And in 1999, he was acquitted of criminal charges stemming from a nightclub shooting that sent his former protege, Shyne, to prison for 10 years.

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His former rival, Death Row Records founder Marion "Suge" Knight, is currently in a California prison serving a sentence for manslaughter.

Knight, 58, issued an ominous warning to Combs in a phone call from prison with the producers of his "Collect Call" podcast, Breakbeat Media.

"I tell you what, Puffy, your life is in danger because you know the secrets, who's involved in that little secret room you guys [are] participating in," he said. "You know they're going to get you if they can."

Industry legends Shakur, signed to Death Row, and Notorious B.I.G., a Bad Boy artist, both died in drive-by shootings before the end of the decade.

Knight was in the car with Shakur when they were attacked in Las Vegas. Biggie, whose real name was Christopher Wallace, died in the arms of one of Combs' bodyguards.

The cases prompted speculation and conspiracy theories for more than a decade. Police in Las Vegas finally announced an indictment in Shakur's murder last year.