4. Larry Holmes: Record after age 40 – 21-3 (10)

Many observers thought they had seen the last of “The Easton Assassin” when Mike Tyson crushed the 38-year-old Holmes in less than four rounds. Holmes, however, knew differently. After scanning the heavyweight landscape Holmes came to two conclusions: First, the skill level of most heavyweights was terribly deficient, and second, if George Foreman could rake in millions he could too. So, on April 7, 1991, the 41-year-old Holmes launched what would become a largely successful return to boxing.

His opening act was eventful both in and out of the ring. Shortly after blasting out Tim Anderson in 123 seconds, Holmes was confronted by fellow ex-champ – and onetime victim – Trevor Berbick in the post-fight press conference. Even after police ushered Berbick out of the building he continued to berate Holmes. Finally, Holmes had enough. He climbed onto the roof of a car, from which he jumped on Berbick. The two were quickly separated but the moment continues to live on YouTube.

Like Duran before him, Holmes racked up huge ratings on USA’s “Tuesday Night Fights” by taking on mid-level competitors such as Eddie Gonzalez (W 10), Michael Greer (KO 4), Art Card (W 10) and Jamie Howe (KO 1). While the spring had long left Holmes’ legs, his jab continued to be a snappy ramrod and his underrated right cross scored its share of knockouts. 

His 5-0 start garnered the 42-year-old Holmes a pay-per-view showdown with 1988 Olympian Ray Mercer. To the shock of many, Holmes schooled his powerful but raw opponent and at times Holmes was so comfortable in the heat of battle that he turned toward the hand-held cameras and offered his own commentary. Holmes’ 117-112, 117-111, 115-113 decision victory justified another crack at the ultimate prize against the undefeated (27-0) and undisputed heavyweight champion Evander Holyfield.

Billing himself as “The Professor” of boxing, Holmes promised to educate Holyfield just as he had Mercer. Though he was competitive, Holmes’ guile wasn’t enough to neutralize “The Real Deal’s” youth and drive and he lost a unanimous decision.

A still determined Holmes continued to feast on the heavyweights of the day. Victories over Everett “Big Foot” Martin (W 10), Rocky Pepeli (KO 4), Ken Lakusta (KO 7), Paul Poirier (KO 6), Jose Ribalta (W 10), Garing Lane (W 10) and Jesse Ferguson (W 10) placed the 45-year-old Holmes in position to fight WBC titlist Oliver McCall, who was fresh off his shocking one-punch destruction of Lennox Lewis.

Holmes gave McCall all he could handle for the first two-thirds of the match – the bout was even on two scorecards while Holmes led by one point on the third. But McCall turned the tide in round nine by landing several overhand rights, one of which cut Holmes’ eye. Two of the judges scored that round 10-8 despite no knockdowns and that calculation proved pivotal as Holmes lost a 114-113, 115-114,115-112 decision.

Again, Holmes continued to fight on, all the while robustly campaigning for a showdown with Foreman. That fight never took place – they actually were signed to fight January 23, 1999 at the Houston Astrodome before money issues killed the bout – but Holmes comforted himself by racking up more victories.

He won eight of his last nine fights – the only defeat was a disputed 12 round split decision to Brian Nielsen in Denmark – and at age 52 Holmes ended his career with a 10-round decision over Eric “Butterbean” Esch in July 2002. Even at that advanced age, Holmes’ jab – both physically and verbally – remained in prime form, though Esch was credited with a knockdown in the final round.

Nevertheless, Holmes’ post-40 resume ranks among the best. As much as this would rankle him, one must say that an old rival is ranked directly ahead of him.