Tyson with Rooney wins every time. Tyson after 1989 loses, simple as that.
This question asks if a pre-prison Tyson could defeat Evander Holyfield.
That entire surmise depends entirely on one thing:
Was the fight before or after Tyson’s time with Kevin Rooney.
1988 Tyson with Rooney was a better heavyweight than Holyfield, hands down
Up to late fall of 1988, Mike Tyson lived, breathed, boxing. Tyson trained under Cus D’Amato’s system called by most fans ‘Peek-a-boo,’ a term D’Amato disliked. He called the style ‘tight defense’ for the positioning of the boxer’s hands in front of their face, which aided defense in protecing the face and head, and allowed better positioning for the jab.
The system emphasized counter-punching while doing something no other counter-puncher did. Jimmy Young, a legendary counter-puncher, boxed carefully waiting for an opening. Cus’s fighters made their own openings by moving forward aggressively, moving in and out, constantly moving, probing and throwing combinations.
Making Tyson even more effective, a bob and weave, a la Joe Frazier, was added.
The system worked to make three men undisputed world champions, and no one, ever, used it better than 1985 to 1988 Mike Tyson. His natural speed and strength made him a really deadly puncher, with a great defense.
Holyfield at that time had just risen to heavyweight, but wanted to fight Mike Tyson. The fearless, aggressive Holyfield believed he was ready.
He was not.
Holyfield only weighed 202 for his first heavyweight fight. While fast, and a first rate boxer, he lacked the brute strength he added later through extensive weight work and creative chemistry.
At that time, strength, speed, power, agility, all go to Tyson. Conditioning is even. The only advantage Holyfield would have is reach.
It wouldn’t be enough.
Tyson wins up to 1989.
Post 1989 Tyson loses to Holyfield
Don King now held sway over Tyson, who drugged, drank, and whored away. Tyson, who used to stay in fighting shape year round, now ballooned to 300 pounds in between fights. The one time combination master was gone, a one punch slugger in his place.
What was the Don King affect?
1980’s King boxers:
- Mike Tyson
- Tony Tucker
- Pinklon Thomas
- Greg Page
- Mike Dokes
All had their money taken, and their careers ruined by drugs and Don King.
By 1990, Holyfield, through extensive weight work and creative chemistry, had become a rock hard 210 pounds.
All Mike’s advantages were gone:
- Holyfield was stronger, in far better shape, and just as fast
- Holyfield knew if he could move in and force Mike back, he neutralized Mike’s power – he could not have done that in 1988, he could two years later
fanboys talk about Mike being shopworn by the time he met Holyfield in 1996, but they forget a few things that undermines that argument:
- Holyfield was four years older than Mike.
- While Mike had not been taking terrible batterings, Holyfield had 3 absolute wars with Riddick Bowe, including Evander’s first knockout loss.
In other words, by 1996 Holyfield was more worn than Tyson, which is why he was a 25 to 1 underdog in their first fight!
Had Tyson and Holyfield met in 1990 and 1991 as originally booked, I think Tyson would have lost. He was far worse, a lot, lot, worse, than what he was in the fall of 1988 when Holyfield first wanted to fight him, and Holyfield was a lot better than he had been.
Before 1989, Tyson wins hands down, after that, Holyfield does. Mike with his original team was a monster. After that, he was a drug addled shadow of what he used to be.
