Diddy's one legal misstep that unleashed a tidal wave of lawsuits and changed his life forever

Over the course of calendar year 2024, Sean "Diddy" Combs has seen his reputation decline amidst a wave of lawsuits and federal investigations into his activities. Combs' legal troubles compounded throughout the year and he is now sitting inside the Metropolitan Detention Center in Brooklyn, New York, awaiting trial in May 2025 on charges that include racketeering and sex trafficking.

Combs' problems really began when ex-girlfriend Cassie Ventura took him to court over claims of rape and abuse throughout their decade-long romance. The general public looked on with horror when a video from 2016 resurfaced that showed Diddy violently beating Ventura in a Los Angeles hotel -- and according to revelations on a new podcast, Diddy could have changed his life for the better if he had not been so stubborn.

Diddy refused to settle with Cassie

A new podcast called "The Rise and Fall of Diddy" has revealed that the hip-hop mogul was well aware that Ventura was planning to sue him -- but he refused to settle out of court, which led to a breakdown in talks between the pair's attorneys and Ventura ultimately filing suit.

"She came to him before she filed and said, 'I believed I was wronged by you,'" attorney Donte Mills said on the podcast. "I know that both Sean Combs' attorneys and Cassie's attorneys were in conversation, in talks, to see if they can resolve the lawsuit, but they were not able to and those settlement negotiations fell through."

Though he initially denied wrongdoing, Diddy apologized for his actions on Instagram once the 2016 video became public knowledge in May. Two months earlier, federal authorities had raided Combs' homes in Miami and Los Angeles; in September, he was arrested on federal charges.

It is hard to say for certain whether Combs' legal woes would have been curtailed had he reached and agreement with Ventura prior to her filing suit. But Diddy is now disgraced, dealing with a large number of lawsuits in relation to alleged sexual misconduct over decades, and he has been denied bail four times as he waits for what will surely be a highly-publicized trial in 2025.