When Sean “Diddy” Combs’ ex-girlfriend Cassie accused him of sexual assault, battery and sex trafficking in a Nov. 16 lawsuit, his lawyer said the Bad Boy Entertainment mogul “vehemently denied” her “offensive and outrageous allegations.” They reached a settlement the next day. The singer born Cassandra Ventura, who dated Combs for the better part of a decade until their 2018 breakup, stated she’d chosen to resolve the matter “amicably on terms that I have some level of control.” Combs’ attorney said the settlement was “in no way an admission of wrongdoing.” But that was only the beginning of the No Way Out artist’s current slew of legal woes. On Tuesday, Combs pleaded not guilty to federal sex trafficking and racketeering charges after his arrest the night before in New York, according to the Associated Press. The charges were filed almost six months after federal agents conducted simultaneous raids on Combs’ homes in Miami and Los Angeles. Authorities didn’t officially confirm at the time that the searches were connected to what was by then a handful of lawsuits that had been filed accusing Combs of sexual assault. “He’s going to fight this with all of his energy and all of his might and the full confidence of his lawyers,” Combs attorney Marc Agnifilo told reporters outside the Manhattan courthouse Sept. 17. Sons Quincy Brown, 32, Justin Dior Combs, 30, and Christian “King” Combs, 25, were seen arriving at the federal courthouse earlier in the day before Combs was due to appear. Meanwhile, Agnifilo also said that his client had purposely traveled to New York to “basically engage the court system and start the case,” which they knew was coming. But first, there were the lawsuits. On the heels of Cassie’s civil court action, Joi Dickerson-Neal accused Combs of drugging and assaulting her when she was a student at Syracuse University in 1991, stating in her lawsuit filed Nov. 23, per NBC News, that Cassie’s suit “forced her to face his assault again.” A spokesperson for Combs told E! News at the time that Dickerson-Neal’s story was “made up and not credible.” Plaintiff Liza Gardner filed suit the same day, alleging Combs and another singer sexually assaulted her at the latter’s New York apartment in 1990 or 1991 following a music industry event.\ On Nov. 24, the New York Adult Survivors Act-which in 2022 gave adult sexual assault survivors a one-year window to sue no matter when the statute of limitations had passed for the alleged crime-expired. In response, an attorney for Combs told NBC News, “The claims involving alleged misconduct against Mr. Combs from over 30 years ago and filed at the last minute are all completely denied and rejected by him. He recognises this as a money grab. Because of Combs’ fame and success, he is an easy target for accusers who will falsify the truth, without conscience or consequence, for financial benefit. The New York Legislature surely did not intend or expect the Adult Survivors Act to be exploited for improper purposes. The public should be skeptical and not rush to accept these unsubstantiated allegations.” On Nov. 28, Combs’ Revolt TV network announced that he was stepping down as chairman. Combs, who cofounded the digital channel in 2013, didn’t have an operational or day-to-day role in the business, Revolt said in a statement, but “this decision helps to ensure that Revolt remains steadfastly focused on our mission” to create meaningful content for Black audiences everywhere. Days later Combs was sued by a Jane Doe who alleged she was 17 when Combs, former Bad Boy label president Harve Pierre and an unnamed man gang-raped and sex-trafficked her in 2003. After the fourth lawsuit, Combs spoke out on Instagram Dec. 6, calling the accusations “sickening” and charging that the plaintiffs were trying to “assassinate” his character in search of a “quick payday.” He concluded: “I did not do any of the awful things being alleged. I will fight for my name, my family and for the truth.” The lawsuits other than Cassie’s are still pending. But all was quiet on the eastern and western fronts of Combs’ empire for a couple of months. Combs and Pierre filed respective responses to Jane Doe’s suit on Feb. 20, both denying her allegations. In his filing, according to NBC News, Pierre stated he didn’t participate in a sexual assault of the woman, nor did he witness one. The plaintiff’s attorney Michael J Willemin told NBC News in a statement that the “deeply troubling allegations against the defendants by multiple women” spoke for themselves. Then Combs was sued for the fifth time in four months when producer Rodney “Lil Rod” Jones accused Combs in a lawsuit filed Feb. 26 in a New York federal court of sexually harassing, drugging and threatening him for more than a year while he worked on the rapper’s 2023 LP, The Love Album: Off the Grid. An attorney for Combs said in response, “We have overwhelming, indisputable proof that his claims are complete lies.” And months later, days before his arrest, Danity Kane alum Dawn Richard filed suit against Combs alleging sexual assault and other misconduct. His attorney said in a Sept. 11 statement to E! News that his client was “shocked and disappointed” by her allegations. “In an attempt to rewrite history,” the attorney stated, “Dawn Richard has now manufactured a series of false claims all in the hopes of trying to get a pay day-conveniently timed to coincide with her album release and press tour.” Meanwhile, federal agents raided Combs’ Los Angeles and Miami mansions on March 25 in connection with allegations of sex-trafficking and sexual assault, a source familiar with the matter told NBC News, as well as suspected solicitation and distribution of illegal narcotics and firearms. Three women and one man had been interviewed in the course of the investigation, according to the source. Guns were found and confiscated from both properties and Homeland Security investigators seized Combs’ phones in Miami before he was scheduled to leave for a trip to the Bahamas, law enforcement sources told NBC News. Not naming Combs as a target, Homeland Security Investigations New York confirmed in a statement that the agency “executed law enforcement actions as part of an ongoing investigation with assistance from HSI Los Angeles, HSI Miami and our local law enforcement partners.” Meanwhile, Combs’ attorney Aaron Dyer slammed the raids as a “gross overuse of military-level force.” “There is no excuse for the excessive show of force and hostility exhibited by authorities or the way his children and employees were treated,” he said in a statement to E! News. “Mr. Combs was never detained but spoke to and cooperated with authorities. Despite media speculation, neither Mr. Combs nor any of his family members have been arrested nor has their ability to travel been restricted in any way.” On the afternoon his 17,000-square-foot home in LA’s posh Holmby Hills neighborhood and his waterfront Star Island estate in Miami were being searched, Combs was at Miami-Opa-locka Executive Airport, as seen in video obtained by TMZ. Two of Combs’ sons were at the LA house when agents showed up and were made to wait outside, according to KTTV Fox 11, which captured aerial and ground footage of the property during the raid. Dyer’s statement continued, “This unprecedented ambush-paired with an advanced, coordinated media presence-leads to a premature rush to judgment of Combs and is nothing more than a witch hunt based on meritless accusations made in civil lawsuits. There has been no finding of criminal or civil liability with any of these allegations. Combs is innocent and will continue to fight every single day to clear his name.” It’s unclear if Combs ever took off for the Bahamas, but the father of seven was spotted at Topgolf in Miami on March 28 with his twin 17-year-old daughters D’Lila and Jessie. He flashed a peace sign at the paparazzi. Combs publicly marked Easter Sunday by sharing photos of his youngest child, daughter Love, whom he welcomed with model Dana Tran in December 2022. The Instagram slide show featured Love in several pink and floral outfits signaling that it’s springtime. In April 2023, the Holmby Hills house was the scene of an intimate listening party for Combs’ The Love Album: Off the Grid, an independent release from his label Love Records and his first studio album since 2006’s Press Play. He told his guests, per the Los Angeles Times, that his intent was to “bring love back to R&B music.” The album dropped Sept. 15, two months before Cassie filed her lawsuit.