EXCLUSIVE: Another Blow For Diddy! How Lawsuits, Legal Fees and a Destroyed Career Left The Jailed Sex Beast's Bank Account Bleeding Dry
Trump admits he's known Combs for some time but has spoken to the rapper in 'years'.
July 31 2025, Published 6:30 a.m. ET
As jailbird Sean "Diddy" Combs cools his heels in the clink while awaiting sentencing on prostitution charges, RadarOnline.com can reveal the hip-hop horndog may also be facing financial ruin from an avalanche of civil lawsuits and potential lost business deals.
The All About the Benjamins rapper, 55, was recently acquitted of sex trafficking and racketeering charges – but found guilty on two counts of transportation to engage in prostitution, which could earn him up to 20 years in prison.
A judge denied a bail request from his attorney and ordered Combs to remain in custody ahead of his hearing.
Diddy's Big Costs
Cassie Ventura claimed Sean 'Diddy' Combs paid $20 million to silence abuse allegations from their relationship.
Prosecutors had accused the Bad Boys Records cofounder of masterminding a criminal conspiracy that used intimidation, brute force and cash to arrange drug-fueled orgies dubbed "freak offs."
Combs has long maintained that he's innocent – but he's been held in a New York City jail since his arrest in September 2024. Even if he's sprung with time served, experts told RadarOnline.com the former billionaire could see his estimated $400 million fortune siphoned off by legal bills and potential payouts.
According to The New York Times, Combs has been clobbered with more than 50 civil lawsuits from men and women accusing him of sex abuse. His team has denied the charges and suggested that the flood of lawsuits is a money grab.
'Potential To Bankrupt Diddy'
Pete Gleason warned over 50 civil suits could bankrupt Combs despite his $400 million fortune.
Renowned New York City lawyer Pete Gleason believes that Combs has already coughed up "millions" for his defense and told RadarOnline.com: "These lawsuits have the potential to bankrupt Diddy."
Combs promptly settled an explosive 2023 suit lodged by his singer ex-girlfriend Cassie Ventura, who was a star witness for the prosecution.
The BBC reported Ventura testified Combs was an abusive bully, who stifled her career and forced her into "humiliating" drug-fueled hookups with male escorts during their 10-year relationship – and told the court that he paid her a $20 million settlement.
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Devin White said Macy's may drop Sean John's deals as Combs becomes too toxic for business.
Devin White, a celebrity financial advisor for rappers, told RadarOnline.com that he believes Combs, who started the fashion and lifestyle brand Sean John, may also lose major moolah from dashed opportunities.
White explained: "He's going to be radioactive, so his Sean John business deals with Macy's and other stores are going to be finished."
Combs has also put his Los Angeles megamansion on the market for $61.5 million, raising concerns that a total real estate sell-off could possibly leave the scandal-scarred star without a home to hang his hat.
