8. Thulane “Sugar Boy” Malinga: Record after age 40 – 4-4 (2)

For most of his 19-year career the South African was viewed as a largely successful workman who earned his shots at the brass ring but who fell heartbreakingly short when the fateful day arrived. Once he turned 40, though, all that changed. While his post-40 record is marginal, Malinga makes this list for one simple reason: He is the only fighter in boxing history who has captured not one, but two major titles after age 40. If Hopkins beats Cloud on Saturday, he’ll become the second.

Following a 185-10 amateur career Malinga won 25 of his first 28 fights against domestic competition to earn a shot at IBF super middleweight king Graciano Rocchigiani in Germany. But the tactics that worked against South African competition failed to dent Rocchigiani, who coasted to a 119-112, 119-113, 117-111 decision.

The “nearly man” pattern continued through his 30s as he defeated solid competitors like Nicky Walker (W 10), Vince Boulware (W 10) and Jim McDonald (W 10) but stumbled in high-stakes fights against IBF super middleweight king Lindell Holmes (L 12), longtime WBO 168-pound titlist Chris Eubank (L 12), Nigel Benn (a hometown L 10) and Roy Jones Jr. (KO by 6). As he neared the late stages of his ring life his lot seemingly was set in stone – good, but not good enough to take the ultimate step.

Nearly three months after turning 40, however, Malinga’s fortunes took an improbable turn for the better as he secured a rare fourth chance at a major belt. Rematched against Benn, now the WBC super middleweight titleholder, Malinga was cast as the party of the second part as “The Dark Destroyer” prepared to perform before his fans in Newcastle. Twelve masterful rounds later Malinga ended up crashing the overconfident Benn’s party and taking his belt home to South Africa. Malinga’s sharp jabs closed Benn’s right eye by round four and, after coming off the floor in round five, he scored his own knockdown in the 12th to sew up a split decision that should have been unanimous.

Malinga lost the belt four months later by split decision to the awkward Italian Vincenzo Nardiello but in his next fight 17 months later Malinga, now one month past his 42nd birthday, met Nardiello’s successor – the 25-0-1 Robin Reid – for his old belt. Fighting his fifth title fight in 14 months and perplexed by Malinga’s maneuvers, “The Grim Reaper” could never draw a bead and lost by unanimous decision.

Malinga again lost the belt in his first defense, this time to the 22-1 Richie Woodhall, but he bounced back with knockout victories in Denmark over the 26-1 Fredrik Alvarez and the 14-0 Peter Madsen. Those two victories set up a match in Copenhagen with the 28-1 Mads Larsen, who stopped the 43-year-old Malinga in 10 rounds. Ten months later, Malinga ended his career with an eight-round TKO loss to Ole Klemetsen.