On This Day: When John L. Sullivan and Jake Kilrain went to jail

Following their world heavyweight title fight in May, Oleksandr Usyk and Tyson Fury collected sizeable paychecks and basked in the glory that comes along with being the center of the sporting world for a memorable hour.

After John L. Sullivan and Jake Kilrain threw hands for 75 rounds, they went to jail.

It was a different time in America in 1889, and Sullivan and Kilrain were different fighters. And despite engaging in what was basically an illegal activity, that didn’t dilute their popularity. So it was no surprise that after a heated build-up, the two agreed to fight in Richburg, Mississippi on July 8.

Ringside seats were $15, and thousands traveled by train to the “secret” farm where a ring was built the night before the fight. Mississippi Governor Robert Lowry offered a $1,500 reward for the arrest of the combatants, a pittance compared to the $20,000 purse up for grabs thanks to $10,000 being put up by each camp.

This fight of the century, the worst kept secret ever, was the last championship fight of the bare knuckle era, and its anniversary next week is forgotten by most, with the exception of the Bare Knuckle Hall of Fame in Belfast, New York. 

Scott Burt, who runs the hall out of the training barns used by Sullivan in his prep for Kilrain, will celebrate the fight’s 135th anniversary on July 19-20, and Burt, along with promotions like BYB Extreme and BKFC are all doing their part to keep that version of the sport alive. 

To many, bare knuckle boxing is too violent for modern society, but, in reality, it’s largely contested under the rules of modern traditional boxing with a few exceptions. That wasn’t the case with Sullivan and Kilrain, who fought under rules that took the level of brutality and human endurance to quite different heights.

Rounds were not three minutes in length. They ended when a fighter was knocked down or thrown to the ground (yes, throws were allowed). So, in theory, a round could last a minute or an hour. Again, Sullivan, Kilrain and their peers were built different, making them pugilists David Goggins would love.

So when Sullivan and Kilrain made it to Mississippi in 100-degree heat to fight in a ring placed on dirt, not canvas, they were well aware that they would be tested physically and mentally for as long as their bout lasted. Not that either would shed their poker face. Sullivan, “The Boston Strongboy,” famously stated he could “lick any son of a bitch in the house,” and the 31-year-old considered America’s first sports superstar was usually right. Kilrain, 30, was the rising star looking to take the throne. But Sullivan lived as hard as he fought, and after he dealt with a series of health issues, the smart money was on Kilrain to score the upset.

Sullivan had other ideas, and perhaps the old adage that a great fighter always has one great fight left started with him, because he was not going to let Kilrain steal this one from him. That’s not to say Kilrain didn’t have his moments. According to a thorough recounting of the bout by Mike Waters on Syracuse.com in 2012, Kilrain ended the first round in 15 seconds by throwing Sullivan to the dirt, and drew first blood by the time the sixth round closed. But Sullivan battled back and slowly took control. 

It was over an hour by the time round 30 rolled around, and both were sunburned and needing a boost. Sullivan, who refused a request from Kilrain to call the bout a draw, got it from the whiskey his corner mixed with the tea he was given between rounds. Well, briefly, as he later vomited during the 44th round.

Kilrain was in worse shape, with the New Yorker needing to be lifted off his stool and sent into battle. But he kept getting up and kept pressing in the hopes of outlasting Sullivan. It wasn’t to be, though, and as Kilrain walked out for the 76th round after two hours, 16 minutes and 25 seconds, his cornerman, Mike Donovan, threw in the sponge, ending the epic bout in Sullivan’s favor.

Then both got arrested, Sullivan in Nashville, and Kilrain in Baltimore. Sullivan was sentenced to a year in jail, appealed, and wound up with a $500 fine. Kilrain wasn’t as lucky, as he served two months for his “crime.”

It wasn’t the end they deserved after engaging in one of the most memorable fights of all-time, but again, it was a different time. Sullivan and Kilrain eventually became friends, which wasn’t surprising. Ray Mancini once told me that after going through a long fight with someone, he knew them better than their mother, wife or anyone else because he saw what they had on the inside. Sullivan and Kilrain knew each other better than anyone else, and they gained that knowledge over the course of 75 rounds on a farm in Mississippi. 

When Sullivan died in 1918 at the age of 59, Kilrain was one of the pallbearers. That says it all.