As the federal sex trafficking investigation into hip-hop mogul Sean "Diddy" Combs continues, a complex web of high-profile figures with troubled pasts has emerged, shedding light on the dark underbelly of the entertainment industry. Combs, 54, whose mansions in Los Angeles and Miami were raided by Homeland Security Investigations and local police last month, is not the only one haunted by encounters with law enforcement.

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 suggest that if these tapes exist, investigators will be scouring through them to uncover any crimes committed and identify other high-profile figures who may have been present, according to Fox News.

Combs' own father, Melvin Earl Combs, was gunned down in his car when the future mogul was just three years old. Melvin was a drug dealer with ties to former kingpin Frank Lucas, portrayed by Denzel Washington in the 2007 movie "American Gangster." The film also featured appearances by Cuba Gooding Jr., who is named a co-defendant in a sex assault lawsuit against Combs, and rapper, actor, and reality star T.I.

Gooding recently took a plea deal in an unrelated criminal case, avoiding jail time and a criminal record after kissing a woman against her will at a nightclub. T.I. is represented by Shawn Holley, one of Bad Boy's lawyers and a member of the "Dream Team" that defended O.J. Simpson in the mid-1990s. Holley's long list of celebrity clients includes 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 those further removed from the case have bizarre connections to the entertainment underworld. Al B. Sure!, an 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. The spokesperson's son, Khari Noerdlinger, was represented by high-powered defense lawyer Jeff Lichtman, whose clients have included John Gotti Jr., cartel lord Joaquin "El Chapo" Guzman, and now Combs' son, Justin Combs.

Stevie J, a Grammy-winning music producer and close friend of Combs, 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.

Actor Ashton Kutcher, who reportedly expects to be subpoenaed in connection with the federal investigation into Combs, had a friend who was murdered by serial killer Michael Gargiulo, known as the "Hollywood Ripper," in 2001. Kutcher is also a friend and former castmate of Holley's former client, Masterson, who is serving 30 to life in prison for rape.

Combs himself has had a series of violent incidents coinciding with his rise to fame, including a deadly crowd stampede at a 1991 benefit event and his central role in the deadly feud between East Coast and West Coast hip-hop stars. In 1999, he was acquitted of criminal charges stemming from a nightclub shooting that sent his former protege, Shyne, to prison for 10 years.

Combs' former rival, Death Row Records founder Marion "Suge" Knight, issued an ominous warning to the mogul from prison, stating, "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. You know they're going to get you if they can."

Industry legends Tupac Shakur and Notorious B.I.G., signed to Death Row and Bad Boy respectively, 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, while Biggie died in the arms of one of Combs' bodyguards.

Recently, Combs was seen in a more tranquil setting, smoking cigarettes outside his Miami Beach home, possibly reflecting on the tumultuous period that has seen his name entangled in multiple legal disputes, as reported by the Daily Mail. Among the allegations, Combs is accused of creating an environment that facilitated the sexual assault committed by his son, Christian 'King' Combs, with the lawsuit implicating him in both the act and subsequent cover-up efforts.

Grace O'Marcaigh, one of the alleged victims, has come forward with claims of assault aboard a yacht chartered by Combs, adding to the growing list of legal challenges facing the mogul. Her attorney, Aaron Dyer, has dismissed the allegations as "lewd and meritless," signaling a contentious legal battle ahead.

As the federal sex trafficking probe continues, Combs was recently named in a lawsuit as a co-defendant alleging that his son Christian 'King' Combs sexually assaulted a woman working on a yacht he chartered. The suit claims that Sean Combs created the circumstances that led to the assault and paid to cover it up afterward.

Despite the mounting pressure and allegations, Combs and his attorneys have denied all the lawsuits' claims. As the investigation unfolds, the tangled web of connections and troubled pasts of those linked to the case serves as a stark reminder of the dark side of the entertainment industry and the far-reaching consequences of alleged misconduct.