The year 1997 was a good one for Black culture. The movie “B.A.P.S.” was in the theaters, and The Notorious B.I.G.’s “Hypnotize” was at the top of the charts. But it was a somewhat historic June night in Las Vegas, NV, that most people remember most.

Mike Tyson and Evander Holyfield were going head to head in a boxing match, and something unbelievable happened out of nowhere. Tyson bit off a piece of Holyfield’s ear. That bizarre moment changed boxing forever and was a pinnacle moment in Tyson’s public life.

Tyson is a New York native who rose to prominence in the mid-’80s for his boxing prowess. At one point, he boasted an undefeated record, dominating the industry and earning the heavyweight boxing title.

According to ESPN, the 56-year-old would finish his 58-fight career with 50 victories, winning 44 by knockout. In 2011, he was inducted into the International Boxing Hall of Fame.

And while Tyson’s talent in the boxing ring was commendable, his out-of-the-ring antics started to overshadow his achievements as an athlete.

Through the 1990s, he made several headlines that questioned his relationships and social activities. So, while the Holyfield incident was shocking, it marked the start of a long string of activities that became increasingly rambunctious.

After the infamous fight, ESPN also reported that the Nevada State Athletic Commission rescinded Tyson’s boxing license, blocking him from competing for a year.

His rollercoaster of life events ultimately impacted the fortune he earned throughout his career.

Today, the iconic boxer has an estimated net worth of $10 million. However, according to The New York Times, Tyson had earned at least $400 million before filing for bankruptcy.

Let’s look at what led to Mike Tyson losing his multimillion-dollar fortune and how he has worked to gain financial redemption.

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In 2003, The New York Times report noted that Tyson had officially filed for bankruptcy after years of financial struggles.

One of the factors that led to his struggles was his lavish lifestyle. It’s been reported that Tyson would acquire thousands of dollars worth of jewelry at a time. At one point, he spent $173,706 on a gold chain while visiting a Las Vegas jewelry store.

“Knowing him for so long, I gave him the merchandise and knew he’d pay later,” Mordechai Yerushalmi, the store’s owner, previously told The New York Times in a phone interview. “He had open credit with me.”

Yerushalmi added: “He’s been through his ups and downs. He will make good on it.”

Lavish spending habits like this contributed to the $23 million debt he had accumulated over the years.

“I didn’t think I’d make it through my 30s,” Tyson said in 2017 at the SALT Conference, according to CNN Business.

At one point, Tyson could command $30 million payouts for each fight. However, eventually, that no longer became the case.

According to The Herald-Tribune, Tyson had outstanding taxes owed to the IRS and hundreds of thousands of dollars worth of payments due to former lawyers, financial manager Barry Hankerson, a former boxing trainer, and a music producer.

Tyson also owed over $51,000 in back child support, and his assets reportedly ranged anywhere from $10 million to $50 million, according to the filing.

In total, the former heavyweight champion had $27 million of debt in his bankruptcy filing.

”I have been in financial distress since 1998, when I was burdened with substantial debt to Showtime, taxing authorities, and parties to litigation,” Tyson said in an affidavit. “Since that time, although my fight income, various asset sales, and litigation recoveries have enabled me to pay a lot of my debt, I am still unable to pay my bills.”

The New York Times noted that any redemption during that time would have to come from his $100 million lawsuit against his former manager, Don King, for misleading contract terms.

“If financial salvation for Tyson exists, it is not in a rematch with Lennox Lewis, a third go-round with Evander Holyfield, or a fight against Roy Jones Jr.,” the outlet reported in 2003. “It rests with Tyson’s $100 million lawsuit against his former promoter, Don King, alleging that King duped him into signing a contract while he was still in prison for rape and siphoning off millions of dollars.”

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However, in the previously mentioned CNN Business interview, Tyson credits his wife, Lakiha Spicer, and other family and friends for his redemptive story.

Since filing for bankruptcy, Tyson has appeared in television shows and movies including “The Last O.G.” and “The Hangover.” He is also behind his own cannabis brand, which has an edible option that pays homage to the infamous ear situation.

Tyson even returned to the ring to fight former boxer Roy Jones, Jr. in 2020. The two earned $1 million each for the fight.