John Sullivan was a bad ass bareknuckle boxer.

John L. Sullivan: The Last Bareknuckle World Champion and One Bad Mf’Er

John L Sullivan was born in Boston, Mass., to Irish-immigrant parents in 1858. Initially known as a baseball player, Sullivan had success on semiprofessional teams in the Boston area. He was eventually offered a contract to play professionally in Cincinnati but chose to pursue boxing after beating a professional in an exhibition. The “Boston Strong Boy,” as he was called by the press, amassed a stunning record of professional fights, and he finished his career at 47-1-2 with one no-contest fight. 

John L Sullivan and His Early Exhibitions

In between true professional fights, Sullivan was well known for going on exhibition tours where he would travel through the United States or parts of Europe, arrive in a new town and challenge all comers to fight and wager money. He is attributed with this famous quote from one such scenario, wherein he loudly proclaimed, “I can lick any sonofabitch in this bar” (when saying that meant something different than it might now). Some sources claim Sullivan amassed over 450 of these exhibition fights and never once lost.

Like many great fighters, John L. was notorious for his battles with liquor. He could always be found at the local bars when touring through Europe or the States. A spectacular drinker, Sullivan was said to be able to drink beer steins full of bourbon and was literally held captive by one of his trainers during his training camp for a world title bout in an attempt to keep him sober. On multiple occasions, John L. escaped from camp and was rounded up at the local bar and brought back. 

Bloddy Batterings

Boxing today is a remarkably tough and dangerous sport, but the prominent rules during John L. Sullivan’s prime, the London Prize Ring Rules, make modern boxing seem almost watered down. For starters, London Prize Ring Rules fights were bareknuckle. This meant fighters’ faces were far more bruised and cut than today’s fighters, and their hands broke much more easily.

Fighters were also permitted to wear cleated shoes for traction, and corners were allowed to assist fighters off the ground back to their corners. In addition, rather than a set number of rounds and a time limit for each round, rounds ended when a boxer was sent to the canvas either by punch or hip toss. Once that happened, the round concluded and both fighters retreated to their corners for a 30-second break. If a fighter could not answer the bell by the start of the round, the fight was over. Because of this ruleset, some fights lasted hours and upwards of 75 rounds.

History has remembered John L Sullivan so well because his reign as champion marked the end of an era in boxing. In fact, the defining fight of Sullivan’s career was the last heavyweight world title fought with bare knuckles under the London Prize Ring Rules. In 1889, 3,000 people traveled secretly by train to a sleepy Mississippi town to watch John L. square off against Jake Kilrain for the heavyweight world title. The crowd was unaware of the location until they arrived because bareknuckle boxing was then already illegal in all of the United States. 

The Fearsome Foe

Many feared Sullivan would be out of shape because rumors of his boozing were rampant. However, his trainer’s efforts to keep him from the bottle seemed to be successful. When John L. entered the ring and disrobed, he revealed a lean and strong 215-pound frame. The fight began just after 10 a.m. The temperature in Mississippi was already over 100 degrees Fahrenheit. 

Detailed accounts of the fight are hard to find, but most agree the first couple rounds ended quickly, with Kilrain landing effective grappling tosses on Sullivan. Round 4, however, lasted over 15 minutes. Shortly thereafter in round 7, Kilrain landed a solid punch on Sullivan’s ear, drawing first blood. Sullivan began establishing his boxing at this point and scored several knockdowns on Kilrain. At the end of round 17, after a particularly brutal knockdown, Kilrain’s cornermen literally had to carry him to his stool and pick him up off it to start the next round. 

Against All Odds

At this point, the fighters started to become truly exhausted. Both became badly sunburned, and their corners struggled to keep them hydrated. Spectators said the fighters were evenly match during the middle rounds of the fight, and momentum shifted frequently. Both men obtained multiple cuts and knockdowns. One journalist went so far as to say that by the late rounds, both men were unrecognizable. In round 44, Sullivan reportedly vomited in the ring, perhaps from the whiskey his cornermen gave him. 

He persevered, however, and eventually wore Kilrain down despite sustaining a lot of damage. At the end of round 75, Kilrain’s trainer, threw in the towel to protect his man. Thus, John L. Sullivan was declared the winner. After this historic fight, the Marquess of Queensbury Rules were adopted for large fights. From there, there was never another true bareknuckle world championship fight. 


Boxers of John L.’s day were not known for longevity. He had a few gloved fights after his historic war with Kilrain but soon after retired. He died in Massachusetts at age 59 in 1918 due to heart failure. Jake Kilrain was a pallbearer at his funeral. 

John L Sullivan was the biggest sports star of his time. He drew constant press coverage and managed to gain the admiration of the higher classes, which had turned their noses up at boxing previously. He developed a gaudy, high-profile and braggadocious public persona that the most financially successful modern fighters recreate to this day. John L. Sullivan was an enormously captivating public figure as well as a stunning fighter, and this allowed him to leave an impression on our culture that has lasted well over 100 years. 

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