Why Holyfield Always Believed He Could Beat Tyson, Even In 1987

By Scoop Malinowski

In the Fall of 1987, Iron Mike Tyson was terrorizing the sport with his explosive power, devastating combinations and physical and mental supremacy. At that time the 21 year old Mike Tyson was 31-0 (27 KOs) and seemingly impregnable and unbeatable, with three dominant 1987 wins vs James Bonecrusher Smith, Pinklon Thomas and Tony Tucker, after winning the WBC title in Nov. 1986 by a second round knockout of Trevor Berbick.

At that time, nobody realized there was a hunter quietly lurking and waiting to strike down Tyson. This fighter had the self belief and strategy to slay the Tyson dragon.

In the 1987 Ring Magazine “Ask The Stars” feature on page 67, Evander Holyfield was asked by BG of New York City, “What makes you think you can beat Mike Tyson?”

Holyfield’s response:  “When we sparred as amateurs, I found out that Tyson’s biggest weakness  was that he couldn’t get past my left jab. He showed me a lot of frustration and I don’t think he’s changed that much.”

At that time, Holyfield was not on the radar of Mike Tyson. The then 24 year old was just a 16-0 cruiserweight champion, fresh off beating Ossie Ocasio by TKO 11 in the summer of 1987 in St. Tropez, France.

Yet still the quiet and humble 1984 Olympic bronze medalist, born in Atmore, Alabama, already had the better of Mike Tyson in his own mind.

Holyfield was promised a title shot vs Tyson in 1990 but it was delayed after Buster Douglas shocked the sporting world by beating Tyson in Tokyo, Japan in late 1990.  Holyfield then was given first shot at the new champion and stopped Douglas with one punch in the third round. Holyfield decisioned George Foreman in his first title defense and was scheduled to meet Tyson in late 1991. Tyson postponed the date due to a supposed injury and then a rape conviction landed him in jail for over three years.

Holyfield and Tyson finally clashed in Nov. 1996. A significant betting underdog, the 34 year old Holyfield confidently encouraged boxing fans to wager their mortgages on him to defeat Tyson, who was a 30-1 favorite. Also at the pre-fight press conference, Holyfield respectfully declared that he had been “everywhere Tyson has been except for jail” and that the way to beat Tyson “was to box him but you also have to fight with him.” Commander Vander vowed that the titles would be in his hands after the fight. Tyson erupted in a rage and shouted angrily at Holyfield on the press conference dais, evidently offended by Holyfield’s low-key confidence.

Of course, Holyfield famously backed up his words and defeated Tyson by knockout and then won the rematch a year later by disqualification after having his ear bitten off by an extremely frustrated former champion who insisted he was intentionally head-butted.

But the root of the Holyfield-Tyson upset was rooted far back during amateur days sparring, where Holyfield discovered the key weapon to conquering Mike Tyson was his left jab.