Mike Tyson, considered a heavyweight boxing legend, earned millions during his two-decade career. He used a significant portion of his money to grow his car collection. Unfortunately, following years of financial mismanagement, Tyson went bankrupt in 2003. To pay his debts, most of his vehicles were auctioned.

These days, Mike Tyson rides in luxury in a V-12-engined Rolls-Royce Ghost. The vehicle regularly features on his Instagram page. Mike Tyson’s financial struggles are behind him – he runs a lucrative marijuana business. Still, he doesn’t make as much as he used to during his prime. Back when Tyson made tens of millions of dollars a night, he acquired some pretty impressive rides, and here are 10 that stood out.

Cadillac Seville

Mike Tyson’s 1985 Cadillac Seville was his second Cadillac, on top of the Eldorado bought for him by his co-manager Jim Jacobs as a reward for his imperious young boxing record. The Seville’s looks split opinion: some people applauded the vehicle’s upright front end and hunchback rear; others thought the design looked weird.

Rolls-Royce Silver Spur

Mike Tyson wanted to reward himself with a Rolls-Royce after winning the WBA world title in 1986. However, his co-manager, Jim Jacobs, advised him to wait until his 21st birthday. Dutifully, Tyson postponed the purchase. The boxer was barely 21 when he walked into a dealership and bought a Rolls-Royce Silver Spur for just under $150,000.

Rolls-Royce Corniche

As a reward to himself for winning the IBF world title in 1987, Tyson splurged a little over $200,000 on a Rolls-Royce Corniche. The Corniche n ame first appeared on a late 1930s prototype. Despite extensive testing, the vehicle was never manufactured: the prototype was blown up at a dock in France in the early days of World War II.

Bentley Continental SC

The Bentley Continental SC started life as a Bentley Continental R in 1991. It was expensive, luxurious, and moderately fast. In 1994, Cosworth twe aked the engine, increasing its horsepower by about 40. In 1996, Bentley released the Bentley Continental T, a short-wheelbase variant of the R, which looked sportier and featured a 400-horsepower engine.

Mercedes-Benz SL-Class 560 SL

By the late 1980s, Tyson was hanging out with celebrity aristocracy. The boxer developed a close bond with the late rapper Tupac Shakur, who owned a Mercedes-Benz SL-Class 560SL. Naturally, Tyson bought one as well. The Mercedes-Benz SL-Class was an overwhelming success for Mercedes-Benz in the 70s and 80s.

Ferrari F50

After serving a three-year sentence and clobbering Frank Bruno to regain his title, Mike Tyson rewarded himself a Ferrari F50. The F50 featured a 4.7-liter engine derived from Ferrari’s F1-spec 3.5-liter V-12. It produced 512 horsepower, 41 more than its predecessor, the F-40, which had a turbocharged V-8 engine.

Jaguar XJ220

Following his infamous disqualification against Evander Holyfield in June 1997, Tyson bought a Jaguar XJ220. The spaceship-esque XJ220 featured a 3.5-liter turbocharged V-6 that accelerated the Jag to a top speed of 220 MPH. The XJ220 made a huge splash when it was introduced as a functional concept in 1988.

Jaguar E-Type

The motoring world agrees that the Jaguar E-Type is one of the most gorgeous cars ever made. It turned heads when it debuted in 1961 and still turns heads today. Unlike most cars of the era, the E-Type didn’t feature a heavy ladder frame chassis. The E-Type (XK-E in North America) had a 3.8-liter engine capable of hurling the lightweight car to a top speed of 149 MPH.

Ferrari 456 GT Spyder

Reeling from his loss against Evander Holyfield, Mike Tyson bought the Ferrari 456 GT Spyder alongside the F50. The Spyder was a convertible variant of the GT, which featured a 5.5-liter V-12 engine at the front derived from the Dino V-6. The Ferrari 456 GT was a beautiful car, but it looked even better with the top down.

Lamborghini Super Diablo Twin Turbo

The Lamborghini Super Diablo was a turbocharged version of the Diablo VT. The Diablo was already a powerful vehicle – its 5.7-liter V-12 produced 485 horsepower. However, some owners, including Mike Tyson, wanted more. 1996 was a tough year for Tyson as he lost Tupac Shakur, one of his closest friends.