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John L. Sullivan Retains His Heavyweight Championship Against Jake Kilrain in a 75-Round Rematch

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The stakes were huge. Sullivan defended his claim as heavyweight champion in a winner-takes-all contest built around a side bet of $20,000, an incredible sum in 1889, and the possession of a diamond-encrusted championship belt.

Sullivan and Kilrain entered the tournament as the two heavyweight title winners of their generation. Their competitive meeting attracted a lot of attention and brought thousands of spectators to Richburg.

The tournament was fought under the London Prize Ring Rules, which are very different from modern boxing. There were no set three-minute rounds. Instead, the round ended when the fighter went down or was thrown. Competitors had 30 seconds to recover before returning to the scratch line to start the next round. The tournament was scheduled for up to 80 rounds.

The fight took place under oppressive conditions, with temperatures reportedly soaring above 100 degrees Fahrenheit in a grass ring exposed to the Mississippi sun.

Kilrain made an immediate impression by taking the opening fall with a quick throw after landing with a left hand. Throughout the first rounds, he frustrated Sullivan by relying on sharp jabs, clinch, and grappling instead of exchanging punches in the center of the ring. In the seventh round, Kilrain drew first blood when he ripped through Sullivan’s ear with a hook.

Sullivan gradually built up his physical strength. Starting in the eighth round, he found success with crushing rights to the body and heavy blows to the jaw that repeatedly knocked Kilrain to his feet. As the fight progressed, Sullivan attacked the ribs relentlessly while Kilrain’s face took more and more blows. In his mid-30s, Kilrain was battling a broken nose, split lips, and one eye swollen shut.

The contest almost took an unexpected turn in the middle rounds when Sullivan fell seriously ill. Suffering from extreme heat and reportedly affected by the heavy food and alcohol he consumed before and during the fight, the champion vomited repeatedly around the 44th round. Seeing an opportunity, Kilrain suggested that the battle be declared a draw.

Rather than accept the draw, Sullivan recovered, floored Kilrain with another punishing body attack and slowly wore down the challenger in the remaining rounds.

One of the defining moments came in the 68th round, when Sullivan landed a loud right uppercut that reportedly knocked Kilrain off his feet. From then on, Kilrain fought almost entirely with courage. He continued to respond to the scratch despite receiving heavy punishment, often going down quickly to gain precious seconds of rest before the next round.

After 75 rounds and nearly 2 hours and 16 minutes of fighting, Kilrain was still a little behind. Bloodied and unable to continue, he was examined by a doctor, who warned his corner that allowing him to fight could be fatal. Before the start of the round of 76, Kilrain’s second, Mike Donovan, dropped the sponge, giving Sullivan the win.

Both fighters left the ring beaten. Sullivan suffered a swollen ear and a black eye but survived relatively well, and most of the blood covering him was Kilrain’s. The authorities soon arrested both camps for their involvement in illegal prize fighting.

The Sullivan-Kilrain fight closed the chapter on the world heavyweight championship fought under the London Prize Ring Rules. Sullivan successfully defended his title, but three years later he lost to “Gentleman Jim” Corbett under the Marquess of Queensberry Rules, marking boxing’s shift from empty prize fighting to glove competition.

Sullivan and Kilrain have finally put their feud behind them. When Sullivan died in 1918, Kilrain served as one of the pallbearers at his funeral. More than a century later, their 75-round fight remains one of the most enduring stories of boxing’s empty era and one of the most epic in the sport’s history.

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