How Many Times Did Mike Tyson Give Away Bentleys to Stop From Getting Arrested In 1988? Boxer Dished Wild Car Stories of His Youth

In his younger years, Iron Mike Tyson had a thing for fast cars, fast living, and fast decisions— habits that frequently landed him in trouble.

By 1988, Tyson was at the height of his boxing career, both in performance and earnings, solidifying his status as the undisputed heavyweight champion of the world. His financial success was staggering, with fight purses, endorsements, and other ventures catapulting his net worth to an estimated $50 million.

Kid From Brownsville

This mindboggling wealth allowed for a kid from Brownsville, Brooklyn, to indulge in a lot of reckless living with his prized car collection that included Ferraris, Lamborghinis, and Rolls-Royces.

In a 2019 interview on the Joe Rogan Experience, Tyson recounted how he once gave away a crashed Bentley to avoid legal trouble. Rogan asked him about having 7 Bentleys back in his heyday and giving one away to stop from being arrested.

“I was married at the time to Robin Givens, and we were in some fast food joint and were ordering food and she went into my pocket, I guess to get some money in my pocket to pay for the food, and she saw some condoms come out,” Tyson said in an interview that has resurfaced on social media.

He continued, “She was mad so she got in the car. Boom! She crashed the car into another that was just parked there. Boom. She hit somebody. She hurt their arm and the cops came.”

“The cops came and said, ‘Hey what happened here?’ I was afraid they were gonna arrest me so I said, ‘Well, nothing happened, officer,’” he confessed, before adding, “It was the guy with a broken arm and I say, ‘Sir why don’t you just take the car? You know you deserve it because you’ve been through a lot.’ … Because I didn’t want to get arrested again. I didn’t have a wife to get in trouble.”

Fearing arrest, Tyson offered the Bentley, worth $230,000, to the injured party to mitigate the situation.

“Why don’t you just take it? It’ll be OK,” he said to the victim. The man allegedly replied, “Hey, don’t tell me that.”

Once he heard that, the famed boxer said he knew the deal was locked in. This incident wasn’t isolated. Tyson had a habit of offering his cars to avoid conflicts.

Another time, in May 1988, Tyson crashed his $180,000 silver Bentley convertible in Manhattan. When two Port Authority officers offered to help him, Tyson insisted they take the car. According to Tyson, the car was bad luck anyway, The New York Times reported.

At first, the officers declined but eventually accepted, which got them in trouble.

Lynn Tierney, a spokeswoman for the Port Authority, said, ”The next day, the commanding officer at the Holland Tunnel command ordered the officers to return the car. At which point they did it. The company the car was registered to, C.J.T. Inc. -Tyson’s a principal of that – was contacted, and they sent somebody down to pick the car up.”

An administrative review would be launched against them for accepting gratuities.

Tyson’s legal escapades were as dramatic as his boxing matches, but living life like a rock star afforded him that kind of spoils. In 1988 alone, he earned $10 million for his fight against Larry Holmes and $20 million for defeating Michael Spinks.

These enormous earnings funded his extravagant lifestyle and car collection, which included the Ferrari F50, Jaguar XJ220, and Lamborghini Diablo VT. Additionally, Tyson cherished classic luxury cars like the Rolls-Royce Silver Spur and Bentley Continental SC.

At one time Tyson had an estimated net worth of $300 million, but over 30 years after he was at his peak he is a completely different man. His reformed life now includes being a softer podcaster and beloved personality.