Legal bills and settlements have severely diminished the entertainment mogul's fortune, and could one day push him into bankruptcy.

Once followed by an entourage, surrounded by all the luxuries of the world, Sean ‘Diddy’ Combs’ currently is spending his time behind bars at the Brooklyn’s Metropolitan Detention Center. He was arrested on September 16,

Two women who claim they were sexually assaulted decades ago by Sean “Diddy” Combs have filed civil lawsuits against him in New York, adding to a list of accusations of violence and sexual misconduct—all of which Combs denies—that continue to mount as the rapper and businessman sits in jail awaiting trial on a federal sex trafficking indictment.

In a new lawsuit, a woman has accused embattled rapper Sean “Diddy” Combs of drugging and sexually assaulting her in 2006 at a New York party, where she says she was “lured” through a radio station contest.

An Alabama woman who says she was raped by Jay-Z and Sean “Diddy” Combs when she was 13 can proceed anonymously, for now, in her lawsuit against the rap moguls, a judge ruled Thursday, Dec. 26. In her written order,

The woman won a radio contest to attend one of Combs' NYC parties, but woke up the next morning at a hospital with no memory of what happened.

According to a legal expert, Sean ‘Diddy’ Combs’ bleak Christmas behind bars is a “reminder of the seriousness of the allegations against him”.