Evander Holyfield’s career has been marred by numerous controversial decisions, including one that sparked a trilogy.
Evander Holyfield has been involved in multiple controversies, from Holyfield being accused of cheating by Bobby Czyz to his highly criticized draw with Lennox Lewis, and Holyfield’s controversial loss to Nikolai Valuev.
One of these questionable moments occurred in 2000 when 36-4-1 Holyfield faced 36-3 John Ruiz.

Evander Holyfield controversially defeated John Ruiz in their first fight
Ruiz had lost only three times going into the fight, including a one-round KO loss to David Tua.
Holyfield, meanwhile, was coming off a unanimous decision loss to Lennox Lewis.
The fight was a close one, though many believed Ruiz was the rightful winner. Yet, after the scorecards were read out, Holyfield snatched the vacant title, and became a four-time heavyweight world champion.

Ruiz complained about the decision, stating, according to BoxRec: “It was highway robbery without a gun […] I won the fight and he knows I won the fight.”
Holyfield and Ruiz rematched in 2001, and, after Ruiz won a unanimous decision over Holyfield, were forced to settle the score in a third and final bout.
This, however, was also inconclusive, as an aged Holyfield fought to a draw with Ruiz, making their trilogy 1-1-1.
Evander Holyfield unsuccessfully stepped into the ring aged 58
In 2021, Triller were putting on an event that pitted Oscar De La Hoya against UFC fighter Vitor Belfort in an exhibition boxing match.

De La Hoya was forced to withdraw after contracting COVID-19, and was replaced with Holyfield, who filled in for him despite being 58 years old and not having fought in 10 years.
The fight went as well as you’d expect, as Holyfield, who made Hasim Rahman’s head swell, was knocked out in the first round by Belfort, who was too young and too fresh for the weathered legend.