December 2025

NEVER SO SWEET SUGAR RAY ROBINSON’S THIRD FIGHT AGAINST BOBO OLSON IS AN ENDURING TESTAMENT TO THE GREATNESS OF BOXING’S MOST HALLOWED HERO by Don Stradley H istory may record it as a simple “KO 2” for Sugar Ray Robinson, but the circumstances surrounding the night of December 9, 1955, when Robinson challenged Carl “Bobo” Olson for the middleweight championship, were anything but simple. The fight was not just about a boxing title; it was about pride, redemption and a legend’s last chance to prove he still belonged. Granted, he entered Chicago Stadium to fight a man he’d beaten twice before, but this was a slightly worn version of

Robinson. He’d left boxing a few years earlier, having compiled a staggering record of 132-3-2, and tried to reinvent himself as a nightclub entertainer. Unfortunately, being a larger-than-life personality with good rhythm didn’t translate into success as a song-and-dance man, which led to Robinson’s inevitable return to the ring. Moreover, Robinson’s taste for high living had drained his finances. Boxing’s shrewdest businessman was broke. When he’d announced his comeback campaign, a promoter in Paris had offered Robinson $100,000 to fight some easy French opponents, but Robinson wanted to test himself against some tough American contenders and work toward a title shot. He took the latter course, but the majority remained unconvinced that this older, fragile Robinson could reclaim his place as the undisputed middleweight kingpin. Robinson won five out of six fights after emerging from his 31-month retirement, yet he was hardly the Sugar Ray people remembered. After a knockout

win in his initial fight back, he suffered a 10-round unanimous decision loss on national television to fringe contender Ralph “Tiger” Jones in January 1955. Then there was a shaky split decision victory against Johnny Lombardo and a highly controversial split decision win over Rocky Castellani. Robinson admitted to the decline in his form, saying after his defeat to Jones, “It’s my timing that’s off ... I have trouble making a man make the mistakes that used to win me fights.” He compensated where he could, throwing more flurries, trying to steal rounds, but he knew better than anyone that something had gone out of him. He kept smiling, though, trying to convince the masses, and maybe himself, that his quest was realistic. Yet there were moments where he probably wished he had accepted the French offer. Just prior to this third fight with Olson, the U.S. government slapped him with an $81,000 tax lien, which

One spectacular flurry sent Bobo Olson sprawling to the canvas.

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