One of the most marketable entertainers who ever lived left far too much to the imagination where his career is concerned.
Prior to his incarceration in 1992, we had possible fights against George Foreman and Evander Holyfield. There were monster fights discussed after he emerged from prison, however most never materialized.
It's tempting to consider that had Tyson stayed with the original team that got him to $21 million dollars for barely half a round against Spinks.
His first billion before the age of 30 could have arrived on a wave of tremendously more satisfying fights than Don King steered him toward.
I've gone ahead and looked at the career that might have been, and compiled a list of mega fights where Tyson could have made around $300 million for these fights alone.
I'd say we'd get better value out of it compared to say McNeeley, Buster Mathis Jr. and Bruce Seldon after he got out of the slammer.
George Foreman was pushing for this fight pre-incarceration for Tyson. A post-Holmes Tyson might have made for an incredible match against Foreman. Foreman absolutely crushed a game Gerry Cooney in 1990. Both Foreman and Tyson still had an incredible air of menace with their punching power at this stage.
It's a very attractive time to imagine them both putting on the best match possible given their respective ages and points in their career.
So you have the two stages when this fight could have happened: pre- and post-prison for Tyson. Remember that Foreman's comeback began in 1987 and he beat Michael Moorer for the heavyweight title in 1994.
Tyson went to prison back in 1992. Big window for George and Tyson to have what would have likely have been the biggest grossing fight of all time back then.
George fought his last fight against Shannon Briggs in 1997. So, we had another 2 year window after Tyson got out of prison.
A fight in this period presents its own intriguing factors.
Tyson was greatly diminished and rarely punching in combination, with questionable stamina a growing concern. His focus on boxing was waning and he was abusing substances that were taking their toll. Foreman, by contrast, was still competitive with the top fighters in the division. He had a new found drive to assert himself each and every occasion he stepped into the ring.
Most likely Foreman and Tyson would have gone toe-to-toe in some quest to determine for each other, if not all of boxing, who the biggest puncher in the history of boxing truly was. With both fighters haven proven on several occasions they were able to take a serious punch, the theatrics of the first one to really crumple and breakdown could have made the finale of the contest indelible.
It's a crying shame David Tua and Mike Tyson never had the rivalry they deserved.
While only six years apart in age, they seem of completely different generations in boxing somehow.
Tua was a tremendously dangerous heavyweight presence each and every time he entered a ring. While Tyson was a far more refined boxer in terms of skills, the two fighters had equally destructive punching power and tenacity. Where Mike Tyson was the first boxer to drop Michael Spinks, Tua's annihilation of John Ruiz in a matter of seconds laid the foundation for him being Tyson's heir apparent in the division.
But it never happened.
As with Tyson, Tua's dedication and weight fluctuated wildly between fights. Tua was never able to achieve the promise of his devastatingly auspicious beginnings. One of the most intriguing factors of this fight is the physical dimensions and tools of the two fighters. Both Tua and Tyson had remarkably sturdy jaws and confidence that one punch to end a fight at any moment.
Given the characteristics of both fighters, if they met up with each other early enough in their careers, the explosiveness generated between Tua and Tyson could have offered something comparable to Lyle vs Foreman and elevated their pay days for ensuing rematches into the stratosphere.
Shannon Briggs had the Brownsville pedigree and Tyson's original trainer in Teddy Atlas at the outset of his career.
Briggs had tremendous physical assets in the ring and, early on, was touted as the next Tyson by HBO on his way to glistening career. Sadly Shannon's career derailed early on.
However, surprisingly, Briggs rebounded and continued (and continues today) to take on the biggest fights available to him. Along the way, he fought Mercer, Foreman, Lewis and most recently, Klitschko.
Shannon's career began back in 1992, the same year Tyson was locked away. So we'd have to wait until 1995 before their careers could collide.
By 1995 Tyson was 29 to Shannon's 24. Shannon would have been undefeated at that point and riding a fierce wave of early knockouts.
By 1996 Briggs had been exposed. His comeback went well until he faced a prime Lennox Lewis in 1998. Briggs showed tremendous heart in that fight and nearly stole it in the first round.
I'd like to imagine Tyson-Briggs taking place inside that window, say 1997.
This fight has no business being on this list aside from how much fun it was to watch Tyson early on in his career, bringing gigantic white men down all over the canvas.
The other element that makes it interesting is that Cooney could punch. Witness his mauling of Ken Norton and tell me any heavyweight catching one of those hooks could have have stood to take another.
Say what you want about Gerry Cooney, but he was a game fighter who threw bombs every chance he could get.
I can't think of anybody who would just be more fun, style-wise, against Tyson.
Ike "The President" Ibeabuchi should've become the most dominant heavyweight fighter of his era.
He beat David Tua in one of the most remarkable heavyweight contests ever fought in terms of energy expended and his knockout of Chris Byrd.
It was the last fight he had before his bizarre downfall and promised more excitement than anyone else since Tyson.
Ibeabuchi was a beast. Ibeabuchi broke records for most punches thrown against Tua, and nearly every punch was an atomic weapon.
Keep in mind Ike hovered around 240 pounds and was blazingly quick and as fierce as anyone to drive his fist against the back of your skull.
While Tyson rarely ever fought as an underdog, I don't like a post-prison Tyson's chances against what Ibeabuchi brought to the table.
Ike had tools I've never seen before or since in the heavyweight decision.
When he beat Chris Byrd, who was slick as they come (and how I loathed every second of watching him with his constant goofy facial expressions), he wasn't just overpowering him, he was beating him to the punch.
There was something obscene about watching Ike Ibeabuchi fight, he was so good and powerful. And due to him being a horrifically messed up human being, we'll never know where his career could have gone.
It's fun to imagine it crashing into Tyson at some point.
They sparred once before Cus D'Amato up in Catskills.
Apparently, Tyson started off well in the early part of it, Lewis started to figure him out and got the better of Tyson toward the end.
D'Amato assures that these two future kings of the heavyweight division were on a collision course.
When they finally met in Memphis, Tyson was far too faded and broken down inside and outside the ring. I don't say that Tyson at any stage of his career could ever have beaten a prime Lewis, but the one I like with the best chance was the Tyson who entered the ring against Spinks.
His reflexes, focus, and confidence were all at their peak on the night Tyson blew Spinks out of the water.
Nobody else in history ever faced that Mike Tyson.
And yet, I'm still not confident Lewis couldn't have knocked him out. No heavyweight who ever lived wouldn't have been given trouble by Lennox Lewis. While I never cheered for him, I think he's one of the most underrated boxers of all time.
If Tyson was given trouble by Tony Tucker during his "invincible" phase, imagine Lewis bearing down on him. Then again, that Tyson was more capable of capitalizing on a mistake than any fighter in history.
Lewis, over the course of his career, made two mistakes. Both had him blinking up at the lights.
Freddie Roach told me once that James Toney was the most skilled boxer who ever lived—and the laziest.
Toney is a primary color in the paint kit of boxing. There's never been anything like him. How could a fighter so incredibly talented enter the ring clinically obese more often than not? Yet he did. He was game to fight anyone and, most amazing of all, he nearly always won.
Toney's dismantling of Holyfield is a study of destroying a man's willpower. It's like Tyson-Holyfield in reverse.
Toney steals Holyfield's heart and playfully sticks his tongue out along the way just to remind the world who the real warrior is.
I'd like to say I'd handily favor Tyson against Toney; only because Tyson nearly always entered the ring supremely conditioned and Toney was a corpulent tub, but I can't do it. I can't bet against Toney's willpower, determination, and ability to psyche-out Tyson and break him down.
How many years was Toney fighting at heavyweight after starting up at under 160?
How many times did it cost him to be fighting such huge guys?
Never. He was never knocked out. He improved. He enjoyed the challenge.
It's those elements that worry me most against Tyson.
Toney vs Tyson could have been our generation's closest equivalent to Foreman vs Ali in Zaire.
If the timing had been right and Tyson's career had gone a little differently, this would battle would have broken all the records in the modern era of boxing.
If things had gone differently, people might have still wondered if Tyson could escape all the reach and height disadvantages, and reached Wlad's suspect chin.
I picked Wlad over Vitali because I think Wlad's chin is the only element of this fight that makes it really compelling.
I'd still be tempted to say either Klitschko would most likely dominant Tyson at any stage of his career if only because of their skill, power and intelligence in the ring.
While their style makes for boring fights and an overwhelming lack of popularity for the Drago Brothers, I still can't see Tyson overcoming the significance of all the obstacles they'd pose for him.
Holyfield vs Bowe was the best heavyweight action boxing could offer in the 1990s.
They had better chemistry than anyone else in the division.
Lewis and Tyson should have been in that fold early on.
Lewis certainly tried.
Bowe chickened out against Lewis and, for some inexplicable reason, Tyson vs Bowe never seemed even close to a reality. It's a shame. In both their primes, this is a much harder fight to call than Lewis vs Tyson. It's infinitely more interesting in many ways.
Bowe and Tyson both offered tremendous promise and never came close to realizing it in their careers. Had they met during their first rise to prominence, it could have been something extraordinary.
I prefer to think that version of their fight rather than some bogus contest cashing in on the name recognition, where it amounts to nothing more but a bar room brawl.
Don't kid yourself. If the Buster Douglas who fought Holyfield stepped back into the ring against Tyson, Tyson would've creamed him (or bitten off his head).
It's inescapable. This is the biggest of all possible Tyson fights that never happened.
After the biggest upset in all of sports, we all needed something further to resolve the shock. We never got it. Only what might have been.
The Douglas who fought and destroyed Tyson never fought before or since that night in Tokyo. I don't see any reason to suggest he would've returned. But, just for fun, let's say he did come back and a fully determined Tyson rehired the coaching staff that got him to Spinks and fired Don King and, presto, we have the best Mike Tyson available for a rematch.
Each fighter in 1995 is being offered $40 million for the rematch, the tension builds, it's being fought in Dubai on a man-made island of gold etc, etc.
Tyson in two rounds.
The first one was luck. We all saw Douglas counted out well before that awful mess in the 10th.