Tyson vs. Dempsey: The Ultimate Heavyweight Dream Fight

24.08.06 – By James Slater: The idea of dream fights appeals to many fight fans. Close your eyes and picture what you think would have happened between one legendary fighter and another, and your imagination can come up with all kinds of scenarios. Your opinion may change from time to time, too. While in the minds of some avid fans, the outcome between one of their idols against a current champion will constantly remain unchanged. They cannot even contemplate the notion that some guy who reigns today would have been able to have lived with their hero, and if anyone else were to suggest that the fighter they so admire just might have been beaten by another boxer, their anger would be quite passionate.

The fictitious fight that is the subject of this article may very well be one that inspires such disagreement and fury. But before anyone gets mad, let me just say that my opinion – of what the likely outcome would have been had a peak Mike Tyson met a peak Jack Dempsey – is just that, an opinion. No-one is setting out to offend anyone.

Jack Dempsey was, and to my knowledge still is, one of Mike Tyson’s ultimate idols. This is just one of the reasons that makes a dream fight between the two so fascinating and appealing. Both were huge punchers. Both were considered vicious in the ring. And both were massively popular – in fact, still are. But who would have emerged the winner had they fought when both at their absolute peak? I give my judgment here.

The fight takes place in modern times, 1987 – a year when Tyson was bristling with greatness. Therefore Dempsey must adhere to modern day rules, such as going to a neutral corner if and when a knockdown is scored. The Dempsey that Mike faces is the 1919 model and the fight is scheduled for fifteen rounds, as some fights continued to be in ’87. And finally, modern day gloves are used – lets say the Reyes variety.

With the rules noted, Let’s get ready to rumble!

Round one.

Tyson, who was pacing back and forth relentlessly in his corner during the pre-fight intros, comes tearing out at Dempsey at the sound of the opening bell. The two men meet in ring centre, and the slugfest begins. Tyson is the more polished fighter of the two, while Dempsey, though somewhat crude, is more than capable of adapting to the technical advantages Tyson has over him. Both men lock horns in the same portion of the ring they have been occupying since the bell and throw blows with seriously bad intentions. It’s clear from the outset that both men crave a brutal KO. It’s Tyson who has some success first, however. He staggers Jack with a lethal right hand, left hook combination to the head. Seeing his man wobble, “Iron Mike” wastes no time throwing a follow-up attack. He digs a left to Dempsey’s body, followed by another right to the jaw. With this, Dempsey careers across the ring and as he does so his gloves touch the floor. A knockdown is correctly ruled and the referee, Mills Lane, gives Jack the mandatory count. With his gloves wiped, “The Manassa Mauler” braces himself for the charging Tyson. As Mike reaches him, Jack holds on. His strength locks Tyson in a bear-like clinch and a frustrated “Kid Dynamite” fails to finish his man. The bell then rings, signalling the end of a very good round for Tyson.

Round two.

Tyson comes out for round number two in the exact same way he did the first three minutes. They slug it out for a second or two in the middle of the ring, before Tyson decks Dempsey with his trademark right hand to the body, right uppercut to the jaw, left hook to the temple combination. Jack is badly hurt, but beats the count at seven. He staggers towards the onrushing Tyson but as he does so, he stops his advancing foe in his tracks with a wild right hand to the forehead. This buys him some time, and also stuns Mike. The crowd is going absolutely nuts! The savagery of the action is awe-inspiring. Mike then lets a couple of blows hit well below the belt line, yet before the ref can get in to admonish him, Dempsey pays him back in kind with a hard left to the same place. A stern Mills Lane bellows at the pair of them – keen not to let the bout develop into a street fight. After the warnings, Dempsey, sensing he’s taken the best Mike has to offer, bangs away with both hands to the head. Both men are now pounding at each other with seemingly reckless abandon. With hundreds and hundreds of people standing up in the audience, the battle once again takes place in the ring’s very centre. Dempsey is tearing away at a block of iron, while Tyson is winging away at pure granite. Then, Dempsey scores with a screaming left to the jaw and Tyson lurches sideways. Jack runs after him and launches a series of wild hooks, most of which land on the dazed Tyson. “The Mannasa Mauler” is snarling like a ferocious animal and it becomes apparent, out of the two of them, just who is relishing the bruising encounter the most. The bell rings to end a sensational round. One of the best in heavyweight history.

Round three.

Tyson comes out on the front foot yet again, but Dempsey is right there ready for him. Mike lets loose with both hands but Dempsey blocks the punches. Mike now has a somewhat discouraged look on his face. While Dempsey almost appears to be smiling in there. The two men clinch again, but as they do Dempsey uncorks a thunderous uppercut to Tyson’s chin. He follows the hurtful blow with two devastating left hooks to the jaw, and Mike crumbles to the canvas. Feeling pain he has never experienced before in his life, Tyson bravely attempts to rise. But he is gone. His legs collapse underneath him as the count reaches eight, and Mills lane throws his arms into the air. It is all over. Jack Dempsey wins by crushing KO at two minutes and five seconds of round number three!