The two stars were reportedly in a relationship for two years in the early 2000s.

Rapper Sean Diddy Combs has made headlines this week when his homes were raided by federal agents. Diddy’s homes in Miami and Los Angeles were reportedly raided, with the Department of Homeland Security claiming it to be a part of their ongoing investigations, though they reportedly did not confirm if the investigation was related to the rapper himself (via BBC News).

Unfortunately, this was not the first time that the Bad Boys For Life rapper has gotten himself on the wrong side of the law. Sean ‘Diddy’ Combs was reportedly arrested in a late-night club along with his then-girlfriend Jennifer Lopez years earlier in 1999. The detention resulted in a humiliating incident with Lopez, who was reportedly handcuffed to a pole at the precinct.

Jennifer Lopez Was Arrested Along With Sean Diddy Combs

Sean Diddy Combs in the music video of Another One Of Me

Jennifer Lopez and Sean Diddy Combs reportedly had a brief relationship that lasted over two years. According to The Mirror, Lopez and Diddy met while the pop star was trying to establish her singing career with her debut album, which the rapper reportedly helped produce. While their tumultuous relationship was often material for headlines, one incident turned out to be extremely humiliating for the Hustlers star.

In 1999, Sean Diddy Combs and Jennifer Lopez were reportedly partying at Club New York when they bumped into a man named Matthew Allen. Diddy and Allen reportedly had a scuffle during which shots were fired. According to the New York Post, three members of the nightclub got injured because of the showdown.

Jennifer Lopez in Hustlers

After the couple left the club, the two were pulled over by cops after running a light. Lopez and Combs were reportedly along with their bodyguard Anthony Jones when the police found a gun in their car. A retired NYPD detective described the time in the Midtown South Precinct when the couple arrived at the station. He said to The New York Post

“There were all these high-profile lawyers barricaded in the station house waiting to talk to the desk officer. They had J.Lo handcuffed to a pole.”

Another source reportedly said that the pop star was crying and was very upset about the incident (via Daily News). The two left after fourteen hours in detention, with Diddy Combs being charged with criminal possession of an unregistered gun and attempted bribery.

Jennifer Lopez On Her Tumultuous Relationship With Sean Diddy Combs

Jennifer Lopez in Hustlers

Diddy’s arrest reportedly came at a time when the rapper was at the height of his career. The rapper’s music empire reportedly had $130 million in annual sales while his fashion line had also been thriving for a year (via New York Post). The arrest as well as his tumultuous relationship with Jennifer Lopez affected his public image.

Jennifer Lopez has opened up about her two-year relationship with the rapper and how it was her first experience with infidelity. According to The Mirror, Lopez called him her mentor and revealed that their rollercoaster of a relationship ended with a “bang”. She also mentioned to Vibe Magazine (via EW) that he cheated on her while they were together.

“It was the first time I was with someone who wasn’t faithful. I was in this relationship with Puff where I was totally crying, crazy, and going nuts, it really took my whole life in a tailspin…I never caught him but I just knew. He’d say he was going to a club for a couple of hours and then never come back that night.”

The two finally parted ways in 2001, two years after they began dating. Lopez is now married to actor Ben Affleck, while Diddy’s brushes with the law seem to have continued.