Well, that was surprisingly entertaining!

I’m not going to lie; I did not have high expectations for Mike Tyson versus Roy Jones Jr.

After all, when was the last time any of us ordered a Tyson PPV without regretting it?

Before the bout, I had the odds of the two 50+ fighters putting on an exciting show — 15 years after Tyson quit on the stool before the 7th round against journeyman Kevin McBride — somewhere between slim and none.

Well, the former “Baddest Man on the Planet” and Roy Jones Jr proved me wrong and shocked the world last weekend. Their eight two-minute exhibition rounds were an absolute blast – aided, in large part, by Snoop Dogg’s color commentary.

While the bout was officially scored a draw by the WBC judges at ringside, the general consensus is that Iron Mike won handily. Not that winning or losing was the purpose of the event.

“This is better than fighting for championships,” said Tyson after the exhibition, which raised money for various charities. “We’re humanitarians now. We can do something good for the world. We’ve got to do this again.”

Of course, the pay-per-view did more than raise money for charity; it was immensely successful financially. The fight did over 1.2 million PPV buys at $49 each! This is why we’re almost guaranteed to see Mike Tyson in another one of these events in the near future.

The public is already wondering who the former heavyweight phenom will face next.

That includes the oddsmakers at MyBookie, who are already taking action on who will be Mike Tyson’s next opponent.
Who will Mike Tyson Fight Next? Betting Odds
Evander Holyfield -150
Lennox Lewis +300
Riddick Bowe +500
Shannon Briggs +800
Tito Ortiz +1000
One Klitschko Brother +1200
Daniel Cormier +1500
Tyson Fury +2500
Conor McGregor +4500
Logan Paul +5000
Snoop Dogg +10000

The Best Boxing Betting Sites!

Before I get to the Tyson betting odds, I have to make two points:

1. “Real” Boxing is Screwed

In recent years, YouTube personalities competing in celebrity boxing matches have drawn some of the sport’s biggest audiences. Millions of people have already tuned in to watch the Paul brothers, KSI, and his little brother Deji fight in recent years.

The first time KSI and Logan Paul fought, the bout sold 21,000 tickets at the Manchester Arena, generating an estimated live gate revenue of over $3.5 million.

The “white-collar” boxing match generated a total of 1.3 million pay-per-view buys worldwide, including over 800,000 live purchases between YouTube and the KSI vs. Logan Paul official website combined, making it the largest non-professional boxing match of all time.

Their rematch at the Staples Center was streamed live on DAZN and received similar levels of attention.

Its success will undoubtedly start a new trend: legends boxing. As this article highlights, we have not seen the last high-profile exhibition bout between fan-favorite 50-year-olds.

With few exceptions, real boxers are generating nowhere near the attention of YouTube celebrities and the sport’s former greats. Over the next decade or so, all the most successful fight cards will be headlined by novelty acts.


And the hits keep on coming for legitimate boxing! Like clockwork, Floyd Mayweather Jr announced his upcoming bout against Logan Paul, Jake’s older brother.

Over the past few years, Mayweather has brilliantly maneuvered from one absurdly low risk, high reward contest after another.

If a person has a massive following and zero chance of hurting him in the ring, Floyd will fight them.

  • At first, he just waited for boxers to be past their prime, as he did with Pacquiao.
  • It was the Conor McGregor bout that marked the beginning of Mayweather’s “novelty fight” era. And how could it not? He earned over $300 million to beat up a guy from another sport who posed no real threat!
  • Then he went to Japan to beat up undersized kickboxer Tenshin Nasukawa. Fighting for the Japanese Rizin MMA promotion, the two undefeated fighters faced off in an exhibition match under boxing rules – taking away Tenshin’s kicks. Mayweather collected a cool $9 million to knock the 20-year-old down three times, en route to a first-round TKO.

Having squashed an MMA fighter and a kickboxer under his preferred boxing rules, it was time for Floyd to find his next tomato can cash cow.

Insert Logan Paul, a YouTube celebrity and amateur boxer with a whopping two fights under his belt!

The two began planting the seeds for their exhibition a few months back.

This week, Floyd made it official:

If his recent Instagram post is any indication, Mayweather will use Nate Robinson’s recent humiliation as an angle to sell the fight. And seeing Jake Paul smash the smaller NBA star will convince a decent percentage of the idiotic public that Logan has a chance.

“Nate, I’m proud of you and I will always stand behind all my brothers. I will never kick my brother when he’s down. It’s ok for people to voice their opinions on social media, but no black athletes or black entertainers, especially black NBA players should make a mockery out of you. We are supposed to all stand with each other through the good, bad and ugly. I’m here to uplift you and let you know we all love you and congratulate you for just making an effort.

“SIDENOTE: The times I’ve had issues with another brother is when they came at me first. I was just defending myself.”

Make no mistake:

There is no reality in which Logan Paul defeats Floyd Mayweather Jr in a boxing match!

We are talking about one of the best ever to do it – size and age will be non-factors. It takes a lifetime of experience to reach or overcome the level of pugilistic mastery possessed by Money Mayweather.

Fortunately for the two combatants, more people will buy the fight to see the loud-mouth YouTuber humbled than will actually believe he has a chance in hell of beating the 49-0 all-time boxing great. However, it’s another slap in the face to serious professional boxers currently in their prime.

2. Thank God I Didn’t Write a Tyson vs. Jones Jr Preview

Had I written a betting preview for last weekend’s card, I would have come off looking like a real moron. Not only did I think Tyson versus Jones would be awful, but I was also convinced Nate Robinson would beat the breaks off Jake Paul!

What the hell was that, Nate?!

My thinking was this:

  1. Nate Robinson is an elite athlete, one of the few able to reach the NBA.
  2. Not only did he play in the NBA, but he made it there despite being 5’9.
  3. And at 5’9″, he won the freaking dunk contest! Do you understand how much explosive, fast-twitch muscle fiber that takes?!

Sure, Jake Paul has been boxing for a couple of years now, but surely a super-athlete would be able to close that gap with six months or so of training, right?


Apparently, Nate thought it was a smart idea to lunge face-first at his opponent with his guard down.

Over and over again…

I may not be Teddy Atlas, but I’m pretty confident that’s not an effective strategy in the boxing ring.

Poor Nate got smashed and became the biggest meme of 2020 since Tiger King.

If I had written an entire article confidently taking the losing side of that bout, I’d be almost as embarrassed as he is right about now.

Tyson vs. Holyfield III (-150)

The oddsmakers think Evander Holyfield is the likeliest next opponent for Mike Tyson. Holyfield has already beaten Mike twice. The first time was in 1996, a year and a half after Tyson was released from prison. Evander, who was on a comeback tour of his own after losing a championship bout to Michael Moorer in 1994, TKO’d Iron Mike in the 11th round to score the upset victory.

Throughout the first fight, Evander Holyfield and Tyson clashed heads, badly rocking the latter. Re-watching the contests, the headbutts looked intentional to me. Whatever the case, Mike came into their 1997 rematch wary of it happening again.

And like clockwork, Holyfield butted him several times in the early rounds. An infuriated Mike Tyson lost control and bit off the top of his opponent’s ear in retaliation, creating one of the most infamous moments in boxing history.

So, there’s a built-in storyline if the two men decide to fight again. However, I’m skeptical of an athletic commission approving this matchup. I don’t think they’ll trust the two men to follow the strict rules applied to last weekend’s exhibition bout.

Regardless, Evander clearly wants the payday.

American Odds

  • Matchup Odds
  • Evander Holyfield+250
  • Mike Tyson-325

“No more excuses,” Holyfield said in a statement released after the Roy Jones Jr fight.

“This is the fight that must happen for both our legacies. Saturday night you said you were ready to fight me, so sign the contract and get in the ring, Tyson. The world is waiting and it’s on you now. I’m ready.”

Holyfield’s name was initially floated for the first comeback event before promoters decided on Roy Jones.

“My side tried to make the fight happen, and we got nothing but excuses,” the statement continued. “Now, I can see why he wanted a tune-up fight before thinking about fighting me. Roy Jones was a good local opponent for Mike, but a fight with me would be a global event, and the only fight that anyone wants to see is a fight between us.

“There is absolutely no reason why we shouldn’t make it happen.”

There are lots of reasons Mike Tyson and Evander Holyfield shouldn’t happen.

For one, Holyfield is already trying to sell it like a real fight with implications for both men’s’ legacies. Neither of these over 50-year-olds should be competing in anything more than a glorified sparring match.

What happens if they get in there and they clash heads again? Why risk it?

I’m staying far away from this bet at –150 moneyline odds.

Although, I must say:
Interestingly, Mike is a heavy favorite if Tyson vs. Holyfield III does happen.

The 58-year-old Holyfield is a +250 underdog, while Iron Mike’s odds are set at –325.

Lennox Lewis (+300)

There’s absolutely no way Mike Tyson rematches Lennox Lewis.

Last weekend’s fight was entertaining because Tyson was the bigger man.

Roy Jones Jr spent most of his career competing at middleweight and Mike was always a small heavyweight anyway, so the matchup was perfect.

He could get into range and mix it up a little inside and keep the fight exciting for the fans.

Lennox Lewis is considerably taller.

If Tyson wasn’t fast enough to get inside of his long jab twenty years ago, the 50-year-old version definitely won’t be able to.

All of that said, Lennox has teased a possible return to the ring, somewhat motivated by last weekend’s exhibition. However, he’s hinted at facing off with Riddick Bowe, not Mike Tyson.

Riddick Bowe (+500)

Riddick Bowe and Mike Tyson both grew up in the Brownsville section of Brooklyn and have always shared a lot in common. In the 90s, when they were each in their primes, Tyson vs. Bowe was a highly anticipated super fight that never materialized.

Back then, Mike expressed reluctance to face the Bowe, who he considered a friend. Tyson’s prison sentence made the matchup even less likely. Tyson went on to face Holyfield while Bowe took on Andrew Golota, and by the time the dust settled, both men were shells of their former selves.

Like Lennox Lewis, Riddick Bowe is much taller than Iron Mike, standing at 6 feet 5 inches. If he participates in one of these exhibitions, he’ll probably fight Lewis on the undercard of a Tyson headlined event rather than taking on the man himself.

I’m staying away from this bet too.

Shannon Briggs (+800)

Shannon Briggs is an attractive betting option, although I’m not sure he’s a smart choice for Team Tyson.

Briggs was still boxing competitively as recently as 2016 and nearly fought for the WBA title in 2017, before failing a drug test due to “dramatically increased levels of testosterone.”

Side Note:

His blood sample uncovered testosterone levels eight times higher than the usual amount for someone his age and weight!!!

If he agrees to participate in one of these events, I’m not sure Shannon Briggs can dial it back enough to keep things within the realm of an “exhibition.” He’s always been a hyper-aggressive fighter, will 100% be on testosterone or steroids to look his best, and is kind of crazy.

On the other hand…

In May, he told Dame Dash during an Instagram Live chat that he planned to fight Mike Tyson in an upcoming exhibition.

Like Holyfield, I’m guessing Briggs was one of the options discussed by promoters before they picked Roy Jones. So, that demonstrates a certain willingness to do business with Briggs.

I don’t think he’ll be Tyson’s first choice, but at +800, it’s a worthwhile wager.

Tito Ortiz (+1000)

If I were Mike Tyson’s manager, this is the direction I’d go.

Tito Ortiz still has some name value but will keep things light and easy for an exhibition. He’s also not a boxer, which makes for a more entertaining bout since Tyson will be able to land some decent shots and look good again.

I doubt Tito is anyone’s first choice, but at +1000, I like this bet too.

One Klitschko Brother (+1200)

Not a chance.

  • Both Klitschko brothers are way too big for Mike Tyson, standing at over 6’6″ with average reaches of around 80 inches.
  • Wladimir is only 44 and was fighting in major championship bouts as recently as 2017.
  • Vitali is closer to the right age at 49 but is an active politician in Ukraine. He’s currently the Mayor of Kyiv and the head of the Kyiv City State Administration.

Not only would both of the Klitschko’s be a total mismatch for Tyson, but neither has much incentive to get back into the ring.

Daniel Cormier (+1500)

Here’s a direct quote from the 41-year-old recently retired former UFC champion, on his podcast with Ariel Helwani:

“Why would they put me in a boxing match with Mike Tyson? … Nah, I ain’t fighting Tyson. I’m not fighting Mike Tyson.”

Tyson Fury (+2500)

Tyson Fury knocked out Deyonta Wilder in his most recent fight. The two camps are negotiating the third bout, which was initially expected to take place in 2020. However, it’s been pushed back to 2021 at the earliest due to disagreements over the contract terms.

Fury is a 32-year-old current heavyweight champion still in his prime. Nobody would ever sanction this bout, exhibition or not – nor would it be worth the Gypsy King’s time.

Conor McGregor (+4500)

  • Smaller than Mike Tyson? Check.
  • Huge name that will generate tons of PPV revenue? Double check.
  • Willing to participate in whatever event will earn him the most money? Trifecta!

I could absolutely see McGregor agreeing to an exhibition bout versus Tyson if the money were right. That said, they’d have to offer him tens-of-millions of dollars – significantly more than Roy Jones Jr was paid.

Due to the age difference, I think Conor is more likely to take on more competitive aging fighters like Manny Pacquiao or a rematch with Floyd Mayweather Jr than a full-on exhibition bout with Mike Tyson. But you never know!

At +4500 odds, it’s not the craziest bet on the board. It might be worth laying a few bucks on the longshot.

Logan Paul (+5000)

He’s already signed on to fight Floyd Mayweather Jr, so that’s not happening.

Snoop Dogg (+10000)

As amazing as Snoop Dogg vs. Mike Tyson would be, the rapper is far too valuable as a commentator to put into the ring. His remarks were the best thing about the last PPV and will be a huge selling point for future Tyson events.

That said, Snoop is pretty nice with his hands!

Maybe he’ll lace ’em up for an undercard bout someday. After all, Mike Tyson said he smoked weed before the Roy Jones fight. As long as that’s allowed, we can’t count Snoop out completely!