Evander Holyfield Made Millions Fighting Mike Tyson, But Lost it ALL and was Forced to Sell his 109-room Mansion to Rick Ross

Evander Holyfield almost walked away from a storied boxing career before it had even started.

The youngest of nine children, the man who later became the legend, took up boxing having been inspired by a glimpse of a speed bag and thrived under the mentorship of his first coach, Carter Morgan.

The future champion showed natural talent early on and won all of his junior contests for the first three years, but he was then beaten by a young boy named Cecil Collins.

Frustrated by defeat, Evander ran home and informed his mother he was done with boxing, only for her to tell him otherwise.

“When I lost my first fight at 11 years old, I quit,” he explained. “My mama said that I had to go back because she didn’t raise a quitter.

“I lost my second fight [to Collins again], and I quit. She made me go back and try once again.”

Eventually, when they met for a third time, Holyfield conquered Collins.

He returned home and proudly told his mother, who said she was now happy for him to stop boxing.

His response: “I don’t wanna quit anymore!”

From there, Holyfield’s amateur career went from strength to strength and eventually took him to the 1984 Olympic Games in Los Angeles.

The ‘Real Deal’ began to earn his nickname as he tore through the first three rounds of competition with consecutive stoppage wins.

Then, in the semi-final, he met New Zealand’s Kevin Barry and lost by controversial disqualification.

Holyfield had started well in the rugged affair and floored Barry with a left hook just six seconds before the end of round two.

However, Yugoslav referee Gligorije Novicic insisted he’d called a break/stop in action – seemingly while Holyfield was already midway through his combination – and disqualified the American as a result.

Speculation was quickly rife about the intentions of Novicic as the bout he was refereeing between Holyfield and Barry decided who faced his Yugoslav countryman Anton Josipovic in the Olympic final.

Many accused Novicic of deliberately disqualifying the US gold medal favourite to give Josipovic a greater chance of winning.

Nothing was ever proven. The Yugoslav fighter went on to claim gold.

In an astonishing act of defiance though, Josipovic appeared to recognise the ‘robbery’ during the medal ceremony as he pulled Holyfield up from the bronze podium position to stand alongside himself on the gold spot.

Despite this fresh heartbreak, Evander had learned his lesson from childhood and gave no thoughts to quitting boxing.

Instead he turned professional and created a legacy.

Within 12 fights he beat Dwight Muhammad Qawi to claim the WBA cruiserweight title and picked up the other two belts to become undisputed champion not long later.

Then came Holyfield’s boldest move as he began to bulk up to heavyweight so he could chase down the unique achievement of conquering boxing’s top two divisions as undisputed king.

Mike Tyson was initially the firm target, perceived at 37-0 as a seemingly-invincible young superstar.

However, disaster struck when James ‘Buster’ Douglas caused the biggest upset in boxing history by knocking out Tyson in Tokyo.

This turned out to be disaster for not just Mike, but for Evander also.

Eight months later, Holyfield dethroned Douglas by knockout and achieved his ultimate goal, establishing himself as the undisputed heavyweight king after previously achieving the same monumental feat in the division below.

But very few gave him much credit.

As Tyson was such a sensation, large portions of the public refused to accept his loss and various excuses emerged.

They also fairly pointed out that Holyfield had beaten a far heavier and worse-prepared Douglas than the one who had conquered Tyson.

‘Buster’ had spent eight months enjoying his newfound fame, obviously too much.

Holyfield recalled to the BBC: “I was pleased, I reached my goal, but after I reached the goal and became champion, it didn’t stop people from talking.

“I had people saying, ‘He didn’t beat Tyson.’

“Saying, ‘You beat Buster Douglas. You beat a fat Buster Douglas.’

“They were like, ‘You ain’t no real champion, you didn’t beat Mike Tyson.’ And I was like, ‘That ain’t my fault.’

To settle the issue, Holyfield and Tyson signed to face one another, only for the bout to be scrapped due to a rib injury to ‘Iron Mike’.

Soon afterwards, he was convicted of rape and sentenced to six years in prison.

Tyson was gone, and with him went Holyfield’s chance to prove himself as a true champion.

The years that followed were tumultuous for Evander as he suffered his first defeat to Riddick Bowe. He avenged the loss, but was next beaten by Michael Moorer.

After this, he retired as doctors spotted he was suffering with a heart condition in the immediate aftermath of the fight.

Remarkably, upon later having his heart re-examined, it was uncovered that his condition had been somewhat misdiagnosed, seemingly due to the morphine he’d been given following the loss.

Years later it was revealed that the chairman of the Nevada Commission’s medical advisory board believed the champion’s condition to be consistent with HGH (human growth hormone) use.

In the latter stages of his career, numerous allegations emerged linking Holyfield to steroid use.

He always outright denied using performance-enhancing drugs.

Regardless, with medical examinations passed, Holyfield returned to the ring only to be beaten by Bowe in their trilogy bout.

Tyson returned from prison and regained the WBA title before deciding to give Evander what was expected to be his final title shot.

With multiple defeats now on his record and question marks surrounding his health, Holyfield shocked the world by standing up to Tyson, bullying the bully and knocking him out in round eleven.

His mother’s decision to instil her son with the inability to quit proved crucial.

Victory over Tyson cemented Holyfield’s legacy and finally saw him win over any public approval that was somehow still lacking.

In their infamous rematch, Mike was disqualified for biting Evander’s ear out of frustration as the bout began to go the same way as their first meeting.

Holyfield was now hugely rich, a worldwide superstar and then stopped Moorer to avenge that defeat also.

His position on top of the world would once again not last though, as after a controversial draw in their first meeting, Lennox Lewis removed any doubts by beating Holyfield in their rematch.

The ‘Real Deal’ remarkably continued fighting for another 12 years and had his last contest in 2011, at the age of 48.

Sadly though, there were some more sinister reasons for this, other than just a refusal to quit.

At the height of his stardom, Holyfield splashed out on a 109-room mansion in his hometown of Atlanta – a monument to his success.

In 2008, financial difficulties saw the house on the verge of being auctioned off due to foreclosure. Rapper Rick Ross acquired it for $5.8million.

Three divorces had a sizeable impact on Holyfield’s wealth, with failed business ventures and child support payments to eleven children (by six different women) also taking their toll.

The former champion earned hundreds of millions across his career, but some reports claimed he’d lost pretty much all of it.

Thankfully, nowadays Holyfield is clearly in a better place financially and dreams of one day reclaiming his old home.

He’s even recently teased a potential ring return to stage exhibition bouts for charity, though it’s unclear whether or not this will come to fruition.

The Holyfield name is even now being carried forward by a couple of Evander’s eldest children.

One son Elijah, 22, is an American NFL running back for the Philadelphia Eagles.

Another son Evan, also 22, has started his professional boxing career at light-heavyweight with a record of 4-0.

As for his own boxing legacy, Evander was asked by the BBC in 2015 how he’d like to be remembered.

Holyfield simply replied: “The guy that fought ’em all, and did it the right way.”

Adapted from Talk SPORT