Excellent question Irene! I've always maintained that Charles "Sonny" Liston was one of the meanest and baddest cats ever to step inside of a boxing ring and when he was truly at his best, he had a devastating bone shattering left jab that could be compared to a pole axe. Not only was he a powerful puncher, but he was also a pretty decent boxer that set up all his power shots. Anybody that stood toe to toe with Sonny and actually fought him usually wound up being counted out or stopped in some manner. Evander Holyfield when you think of ring warriors usually comes to mind. His ring wars with Bowe are some of the best fights as far as ring drama you could imagine and Evander could really fight too starting as a cruiserweight before moving up in weight and bulking up. He had excellent boxing skills and speed and of course a ton of heart and determination much like the great Marciano did. The closest opponent Holyfield had that resembled Liston was an older Foreman who was just too slow for Holyfield though he did land some god shots and fought a good fight. A younger version would have been closer. But Foreman didn't have as good a jab or as good of boxing skills and stamina as Liston so that's where the comparison ends. Here is a rundown of each fighter:

Sonny Liston

Best wins vs Cleveland Williams (2) Floyd Patterson (2) Zora Folley

Evander Holyfield

Best wins vs Mike Tyson (2) Riddick Bowe, George Foreman

The fight

The excitement is in the air as Liston attempts to intimidate Holyfield with his famous scowl in ring center. As the first bell rings Liston immediately snaps Holyfield's head with a hard jolting jab. Holyfield moves around Liston firing his own jabs as Liston is the aggressor. Holyfield lands a good combo at the bell. In rounds 2-5 Holyfield is fighting a smart fight electing not to go toe to toe with Liston but Liston is causing some damage to Holyfield's eye with that great left jab of his. These rounds are basically even. In rounds 6-8 the fighters are going at it toe to toe with Holyfield holding his own but near the end of round 8 Liston sends Holyfield into the ropes and neary down and clearly stunned. In round 9 both men are trading evenly as Holyfield lands his best shot of the fight temprarily stunning Liston. But when he tries to follow up he is met by a thunderous shot from Liston wich sends him down to the canvas. Holyfield gets up at the count of 8 and fights back like the warrior he is as the bell sounds. In round 10 Holyfield's eye is nearly closed as Liston continues to use his reach to good use. Liston lands another big shot which has Holyfield nearly helpless along the ropes and prompts the referee to stop the fight.

Liston WTKO10

Liston was better than both Bowe and Lewis two fighters that gave Holyfield his toughest fights, this one would go badly for Evander. Liston would most likely have had enough to stop Holyfield late, a fighter like Holyfield would take too much punishment, and Liston was one of the most dangerous in history. Heart and bravery would work against the smaller Holyfield, and Evander would pay too high a price to even get to exchanges that he most likely would lose anyway. Just getting past that Liston jab would be difficult, but once inside, Liston's power would be superior to Holyfield's, and Evander would go out on his shield. Liston would win because styles really do make fights, and this is a fight that gives all the advantages to Liston, a smaller guy coming right at him trying to slug with one of the greatest sluggers of all time is a recipe for disaster. Liston by KO because Holyfield would stand and slug where Ali moved and boxed.

It's my opinion that Liston would be just too strong, although Holyfield looks the part, he'd be in with a real threat. Holyfield did excellent in his career, but Liston knocked out teeth and put two fighters out of the game with detached retinas via his pole like jab. I see a tough first couple rounds, similar to the Cleveland Williams/Liston fights, but Holyfied had the combinations, but not the power to KO Liston. TKO stoppage IMO.No referee today would allow the carnage that Holyfield would be taking. If a 42 year old Foreman stays with Holyfield then a prime Liston wins in a tough one.

Sonny Liston would definitely win ,this man was a freak and an absolute devastator for his opponents ,if in a ring you were caught by one of his punches you were doomed to be brutally knocked out ,One of the boxers that followed Sonny Liston's style was George Foreman and we all know how good boxer George Foreman proved to be .Sonny Liston would only lose to guys with unorthodox boxing style and remember he lost to Muhammad Ali (then Cassius Clay) because Ali was too fast and Liston couldn't give him a shot ,Evander Holyfield was not fast or unorthodox to beat Sonny Liston .

Hmmm, that's an interesting matchup.First of all,Liston was a extremely powerful fighter, who was managed by "SHADY CHARACTERS', as were many fighters of the 1950;s and 1960's., so some of his fights were pre arranged.Patterson was no match for Liston's power.As far as Holyfield was concerned, he was a more disciplined fighter, who would have beaten Liston by a stoppage in the late rounds, by changing his tactics and moving faster than Liston could handle.

The Sonny Liston that destroyed Floyd patterson in round 1 to win the World heavyweight title, vs Evander Real Deal Holyfield who stopped Iron Mike Tyson in round 11, in Nov 1996, to win the World Heavyweight Title. Who would win and why?