Sean ‘Diddy’ Combs’ history of legal trouble includes a 1999 arrest with ex Jennifer Lopez — where she was ‘handcuffed to a pole’

Bad boy for life.

Sean Combs, known as Diddy, P. Diddy and Puff Daddy, 54, is in legal hot water.

On Monday, the rapper and hip-hop industry titan had his homes in Los Angeles and Miami raided as part of a federal sex trafficking investigation, according to law enforcement.

Although this is one of his most dramatic incidents, this isn’t his first brush with the law.

His various legal woes have included numerous arrests and assault allegations, and an infamous incident involving his ex-girlfriend Jennifer Lopez.

Here’s a history.

Jennifer Lopez arrest

In 1999, Diddy and his then-girlfriend, Lopez, 54, were arrested on weapons and bribery charges.

On Dec. 27 of that year, Combs and Lopez — who dated from 1999 to 2001 — were partying at Club New York.

When they were leaving, Combs bumped into a man named Matthew “Scar” Allen. Allen pushed back, leading to a fight in which shots were fired. Three clubbers got injured.

Combs and Lopez left the scene in his car and got pulled over after running a light. Police found a gun in the car, which led to the couple getting arrested.

Now-retired NYPD Detective Derrick Parker was at the Midtown South precinct when they were brought in.

“There were all these high-profile lawyers barricaded in the station house waiting to talk to the desk officer,” he recalled to The Post.

He alleged: “They had J.Lo handcuffed to a pole.”

“She was crying all over the place, in the squad room,” a police source told the Daily News at the time. “She was just upset about the whole thing.”

Ultimately, Lopez was absolved after reportedly being detained for 14 hours. Combs got indicted on two counts of criminal possession of an unregistered gun and attempted bribery for allegedly trying to get his bodyguard, Anthony Jones, to claim the weapon was his.

Combs was later acquitted.

However, his protégé Jamal “Shyne” Barrow – who got arrested with them – was convicted of two counts of assault as well as reckless endangerment and gun possession. He was sentenced to 10 years in prison. He served nine before being deported to Belize, where he became a politician.

The UCLA incident

In 2015, Diddy was arrested for allegedly swinging a kettlebell at an assistant UCLA football coach after the coach allegedly yelled at Diddy’s son Justin, now 30, who played on the team. Diddy was charged with assault with a deadly weapon.

But the Los Angeles District Attorney’s Office decided not to prosecute.

No one was seriously injured, and Combs’ reps claimed the mogul was acting in self-defense.

His former personal chef

In 2017, Diddy’s ex-chef Cindy Rueda alleged that she was regularly made to prepare and serve food to Diddy and his guests while they were engaged in sexual acts.

A spokesperson for Combs told Variety, “This is a frivolous lawsuit by a disgruntled ex-employee who was fired for cause.”

In February 2019, the lawsuit was settled for an undisclosed amount.

Accusations from Cassie

Diddy’s ex-girlfriend Casandra Ventura — the musician known as Cassie — accused the hitmaker of rape and abuse this past November.

She alleged that Diddy had a pattern of abuse and control that included allegedly forcing her to have sex with male prostitutes while he filmed them, physically abusing her and supplying her with drugs.

Cassie also alleged in the suit that Diddy forced his way into her home and raped her toward the end of their longtime relationship in 2018.

“Over the years that Mr. Combs abused Ms. Ventura physically and sexually, she again and again tried to escape his tight hold over her life,” the lawsuit stated. “Every time she hid, Mr. Combs’s vast network of corporations and affiliated entities found her, and those who worked for Mr. Combs’s companies implored her to return to him.”

Diddy’s attorney Ben Brafman denied the accusations to Page Six, and claimed that Ventura had been demanding money from Diddy.

The case was swiftly settled out of court just one day after filing.

Additional assault allegations

Following the settlement with Ventura, Combs was hit with additional lawsuits from women claiming he sexually assaulted them.

One anonymous woman claimed Combs and singer Aaron Hall raped her and an unidentified friend in 1990 or 1991, according to a filing obtained by Rolling Stone in November.

“Jane Doe was offered more drinks and was coerced into having sex with Combs,” the court documents claimed.

Diddy’s spokesperson called the claims “fabricated” in a statement to Page Six.

“This is nothing but a money grab,” they said. “Because of Mr. Combs’ fame and success, he is an easy target for anonymous accusers who lie without conscience or consequence for financial benefit … The public should be skeptical and not rush to accept these bogus allegations.”

Accusation of sexual assault from a male employee 

Last month, Diddy was sued by former employee Rodney “Lil Rod” Jones, who accused the rapper of sexual assault while working on Diddy’s 2023 album “The Love Album: Off the Grid.”

Jones claimed the abuse occurred from September 2022 to November 2023.

Combs’ attorney Shawn Holley said at the time, “Lil Rod is nothing more than a liar” who is “shamelessly” seeking money via his $30 million lawsuit.

The March 2024 home raids

Law enforcement sources told The Post that feds moved in to raid Diddy’s homes Monday because they wanted to seize his phones and computers. They also alleged there would be further raids on houses associated with the mogul in New York and Chicago.

Sources further told The Post that the raids were led by Homeland Security Investigations’ Human Trafficking Task Force, based on a search warrant issued by the Southern District of New York.

“Earlier today, Homeland Security Investigations New York executed law enforcement actions as part of an ongoing investigation, with assistance from HSI Los Angeles, HSI Miami, and our local law enforcement partners. We will provide further information as it becomes available,” HSI told The Post.

Diddy’s sons Justin and 25-year-old King Combs were both seen cuffed by officers, although it’s unclear if they were taken into custody.

In connection to this incident, sources told Rolling Stone that at least four Jane Does and one John Doe have been interviewed by New York prosecutors in connection to the sex trafficking allegations and a RICO case.

Just hours after the raids, Diddy was spotted pacing back and forth outside a Miami airport.