J-Lo, Star Island mansion and Booby Trap: Diddy’s Miami timeline much more than music
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Federal probe into music mogul Sean “Diddy” Combs
Sean “Diddy” Combs was indicted on federal sex trafficking charges after his Star Island mansion was raided.
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The Harlem-born rapper, producer and mogul Sean “Diddy” Combs found himself embroiled in serious legal woes as the millennium approached. Those cases, which included gun possession and bribery charges stemming from a shooting inside a Manhattan nightclub in 1999, started in New York — outside of his adopted South Florida. However, his most serious legal troubles appear to be transpiring in Miami.
On Monday, federal agents descended on his $35 million Star Island mansion as part of an investigation into sex trafficking.
READ MORE: What is Diddy facing? Accusations mount as rap mogul’s Miami Beach mansion raided
Diddy, whose wealth once was pegged at $1 billion, has had ties to South Florida for decades. The timeline of the multi-named celebrity making headlines in Miami includes busts ranging from traffic offenses to the events leading up to Monday’s raid on his lavish property on the tony Star Island in Miami Beach.
Diddy’s Miami timeline
▪ April 2001: Diddy, then going by P. Diddy, was on a Miami Beach vacation after being acquitted on gun possession and bribery charges stemming from an argument that led to gunfire inside a Manhattan nightclub he was in with then-girlfriend, actress-singer Jennifer Lopez in 1999. Diddy had produced a track on Lopez’s 1999 debut album, “On the 6,” which was partly recorded at Gloria and Emilio Estefan’s Crescent Moon Studio in Miami.
While on vacation, Diddy was staying at the Oceania at 16445 Collins Ave. in Sunny Isles Beach, when he was stopped by local police twice in four days for traffic offenses.
The first charge was for driving a rented scooter with a suspended driver’s license when police spotted him making an illegal lane change in a traffic jam near The Clevelander Hotel along Ocean Drive. The jam was caused when fans recognized the rapper and started yelling for his autograph, the Miami Herald reported.
Diddy was stopped and charged with the same offense when Golden Beach police pulled him over for speeding while driving a 1999 Bentley.
He was arrested, but not jailed, on the Miami Beach charge, a misdemeanor punishable by a fine of up to $500. His publicist at the time would not comment on whether the traffic infractions and exposure may have sullied Diddy on Miami Beach. Apparently not.
▪ July 2001: While promoting his album, “P. Diddy and the Bad Boy Family...The Saga Continues,” which was largely recorded at Circle House Recording Studio in North Miami, and his film debut in “Made,” which was opening in Miami, Diddy reclined on a cushy, white couch at The Bass Museum in Miami Beach for an interview with the Herald. The New Yorker said he wanted to buy a house in the Miami area. “Something stupid,” he teased. “I just like the vibe here.”
▪ November 2003: Diddy bought his first “something stupid” Miami Beach home, the 14,000-square-foot 2 Star Island Dr., as an LLC, on the wealthy island that has been home for stars like Don Johnson who lived there when filming “Miami Vice” in the mid-1980s, musicians and songwriters Gloria and Emilio Estefan, basketball star Shaquille O’ Neal, pharma exec and philanthropist Phillip Frost and his wife Patricia Frost whose names grace buildings at the University of Miami and Florida International University and downtown Miami’s science museum. Diddy paid $14.5 million. The home, built in 2002, has seven bedrooms and eight bathrooms.
MORE: Take a look at Sean ‘Diddy’ Combs’ Miami Beach homes being raided by the feds
▪ March 2021: Diddy purchased the 5,000-square-foot 1 Star Island Dr. residence, the Star Island property next door to his 2 Star Island Dr. home, for $35 million. The sellers: Gloria and Emilio Estefan, who used the property as a guest house and bought it in 1993 for $1.84 million. The home has a two-story main house with three bedrooms and six and one half bathrooms, an outdoor kitchen and boat dock.
▪ November 2023: Diddy’s ex-girlfriend Cassie, whose legal name is Cassandra Ventura, sued him in New York federal court alleging he raped, physical abused and drugged her for years soon after they met when she was 19 in 2005. The suit added he forced her to have sex with a succession of male prostitutes while he filmed them in the act and blew up the car of a rival suitor, The New York Times reported.
Diddy was photographed by paparazzi from TMZ a day after the suit was settled looking “solemn” on the grounds of his 1 Star Island home.
▪ Feb. 26, 2024: Music producer Rodney “Lil Rod” Jones filed a lawsuit in New York’s federal court that Diddy, his staff and music executives knew about — and were involved in — illicit and unwanted sexual activities, including sex-trafficking, at his homes in Miami Beach, New York, California and the U.S. Virgin Islands.
Jones’ suit claims many of the guests at Diddy’s Miami Beach mansion were sex workers who Diddy forced him to solicit from Booby Trap on the River at 3615 NW South River Dr. in Miami.
READ MORE: Diddy forced music producer to recruit sex workers at Miami strip club, lawsuit claims
“Mr. Combs provided Mr. Jones with an exclusive Bad Boy baseball cap and required him to wear it to Booby Trap on the River as a signal to any sex worker he approached that Mr. Combs was in town and had sent Mr. Jones to recruit them,” the lawsuit reads.
The suit says some of the guests were minors younger than 16 who were plied with drugs and alcohol at Diddy’s Miami Beach abode.
The suit also alleges that Diddy “displayed his guns and bragged about getting away with shooting people” and that he threatened Jones by saying “that he would eat his face.” The suit claims that Diddy shared that he was responsible for the 1999 shooting in New York City nightclub involving rapper Shyne.
READ MORE: Feds’ raid on Diddy’s Miami Beach mansion goes into the night in sex-trafficking probe
▪ March 25, 2024: Agents from Homeland Security Investigations based in New York searched Diddy’s 1 Star Island Dr. home with the help of agents in Miami and Los Angeles and local police. The raid of Diddy’s Miami Beach property was based on concerns that he might destroy evidence linked to Jones’ lawsuit.
A man described as Diddy’s drug “mule” in the lawsuit that led up to the raid of his homes was busted on drug charges at Miami Opa-locka Executive Airport that Monday, as well. At the same airport, federal agents seized Diddy’s phone and questioned him before clearing him to fly with family and friends to Antigua and Barbuda, a twin-island Caribbean nation just east of Puerto Rico.
By Tuesday morning, the plane was at V. C. Bird International Airport in Antigua and Barbuda — but Diddy was not on it, sources on the island confirmed to the Herald.
This story was originally published March 26, 2024 at 6:00 PM.
