John L. Sullivan, the celebrated 19th century fist fighter embodied the spirit of a fighting Irishman. Sullivan left behind more than just a legacy of 40 wins, 2 draws and 1 loss. The Boston pugilist was a transformative figure who helped usher in a new period in ring fighting. He was the last bare-knuckle champion and also, arguably, the first heavy-weight titleholder of the gloved era. 

As a teenager, the 5’10” and 190 lb. ruffian was notorious for issuing challenges in his hometown saloons, stating that he “could lick any man in the house”. The “Boston Strong Boy” toured the country and offered $1,000 to anyone who could last four rounds in the ring with him.

A hard-hitting and hard-drinking fight master, Sullivan got his start inside the ropes before the adoption of the Queensberry Rules, which formally set the code for modern-day boxing in 1889. The new rules of engagement replaced the old London Prize Ring Rules, the bare-knuckle guidelines that disallowed butting, gouging, scratching, kicking, etc. Still, the punch-throwing, blood-spattering sport was illegal and bouts were usually held in secret locations. Sullivan’s 8-round knockout of John Flood in 1881 took place on a barge in the Hudson river to evade authorities.

A year later, in the backwoods of Mississippi, Sullivan took out fellow Irish-American Paddy Ryan to claim the informal title of the bare-knuckle champion of America. The two men had put up $2,500 to vie for the honour in front of 5,000 spectators.

The New England brawler’s fight against Dominick McCaffrey in 1885 was a gloved faceoff described by the press as the “Queensberry glove contest for the championship of the world”. It was boxing’s first heavy-weight title fight using 3-ounze gloves and 3-minute rounds. Sullivan outclassed his opponent with a 6th round decision to become the first modern heavy-weight champion. 

But the legend’s most memorable fight also turned out to be the last bare-knuckle championship contest under the historic London rules. Once again in Mississippi, Sullivan beat, battered and knocked out Jake Kilrain in round 75 of a scheduled 80-round bout. Despite its outlawed status, the encounter with Kilrain in 1889 was one of the first sporting events in the U.S. to receive national press coverage. Sullivan and Kilrain were both brought back to Purvis, and were tried for Illegal Prize Fighting. Just a year earlier, Sullivan had managed to escape French officials after taking on Britain’s Charlie Mitchell in a blood-soaked exchange under the rain in Chantilly, France. That fight was one of his two career draws. 

Sullivan’s reign ended in 1892 at a gloved meet-up with “Gentleman Jim” Corbett. Younger, faster and fitter, Corbett knocked out the defending champ in the 21st round and delivered the only loss of his career. The old champ subsequently retired from boxing and settled into calmer pursuits such as exhibitions, acting, sports reporting and bar keeping. His reputation renowned worldwide, he enjoyed audiences with the likes of President Teddy Roosevelt and the future King of England, Edward VII. 

Sullivan was inducted into the International Boxing Hall of Fame as one of the sport’s pioneers. The Bare-Knuckle Boxing Hall of Fame stands in Belfast, New York where the fighter used to train. Sullivan died on 2 February 1918 at the age of 59.