Richie Akiva is no stranger to the limelight or controversy.

The former nightclub mogul, who found himself in handcuffs on Wednesday, has built a reputation over the years for hosting extravagant parties, mingling with celebrities, and sealing significant business deals. Among his famous connections is none other than Leonardo DiCaprio, a close friend.

For those curious about the man behind the glitz, here’s a closer look at the “Titanic” actor’s longtime companion.

Arrests

Wednesday’s arrest is not Akiva’s first brush with the law. Back in March 2025, he faced legal issues when it was revealed he was driving with a suspended license.

Akiva was taken to New York’s 9th precinct and charged with misdemeanors. According to a source who spoke with Page Six, he faced charges including one count of aggravated unlicensed operation in the second degree and one count of an equipment violation.

It was reported that his license was suspended because of an old unpaid parking ticket.

Club king

Akiva earned his claim to fame as the founder of iconic NYC hotspots 1Oak and Up & Down.

He was also part of Butter Group — which included an array of restaurants and popular nightclubs — with former business partner Scott Sartiano.

In 2017, it was reported that the mogul had plans to open a rock ‘n’ roll bar titled E. Vil (pronounced “evil”), which stands for East Village.

In June 2022, he launched the exclusive members-only club The Ned alongside Ron Burkle and Soho House founder Nick Jones.

Akiva was attached to the business venture as its “brand and creative director,” bringing in celebs like DiCaprio, Rihanna, Emily Ratajkowski, G-Eazy and “SNL” comic Leslie Jones.

Bad business

It was reported in 2023 that he had a falling out with his former Butter Group business partner, Darren Dzienciol. They now hold rival bashes during May’s Cannes Film Festival.

He was also pushed out of his business arrangement at The Ned by February 2024, allegedly due to some behind-the-scenes money haggling, a source previously told Page Six.

Star-studded nights

Akiva first hit the Hollywood scene as a core member of DiCaprio’s entourage since they were known as the “P–sy Posse” on the ’90s nightlife scene. The entrepreneur eventually became known for his wide network of celebrity pals and wild parties.

In 2013, Akiva made headlines after he hosted a multi-city birthday bash featuring stars Steve Wynn, Diddy, Chris Brown and Miguel, whom he met up with at his 1OAK in Las Vegas where Robin Thicke performed “Blurred Lines.”

He followed it up the following day with a private dinner at the Peninsula Rooftop in New York City hosted by Naomi Campbell. They were allegedly joined by guests Jay Z, Timbaland, Anne V and her beau Matt Harvey.

Thicke later appeared at Akiva’s Paris birthday party in 2017. Additional guests included Lenny Kravitz, Kourtney Kardashian and her then-boyfriend Younes Bendjima, supermodels Jourdan Dunn, Taylor Hill, Joan Smalls and Doutzen Kroes.

In more recent years, Akiva has begun hosting his signature shindigs in St. Barts. In 2021, he hosted a New Year’s Eve party on the popular celebrity hotspot island which, a source told us, was jumping with hundreds of people until the wee hours of the morning.

In 2022, he celebrated the launch of his private social club, Societe, with a star-studded event featuring appearances from Busta Rhymes; Ne-Yo and Gunna Alex Rodriguez; Giancarlo Stanton; NBA players Joakim Noah, Myles Turner, and Oshae Brissett; model Joan Smalls, and “Gossip Girl” cast members Thomas Doherty and Whitney Peak.

Over the years, DiCaprio and Akiva have remained as close as ever, with the actor making several appearances at the mogul’s bashes. In 2024, the “Wolf of Wall Street” star was said to have helped out a drunk man at one of Akiva’s epic parties in the Hamptons.