By 1889 bareknuckle boxing matches were illegal almost everywhere in the United States, including the rural Mississippi town of Richburg, where on July 8 John L. Sullivan fought Jake Kilrain for twenty thousand dollars in the country’s last bareknuckle match. At the age of thirty Sullivan had deteriorated into a flabby parody of his top form, but for this fight he trained hard for several weeks. By the day of the match he had lost more than forty pounds and still outweighed Kilrain by thirty.
Sullivan may have been past his prime, but he had more than enough power left to dismantle Kilrain. Though the challenger drew first blood, he managed to stretch the fight out to seventy-five rounds only by backpedaling and wrestling with Sullivan, who cursed and taunted him to “stand up and fight like a man.”
The only moment of suspense for Sullivan’s backers came during the forty-fifth round, when the Boston Strong Boy vomited after drinking a mixture of tea and whiskey; ringside experts insisted that Sullivan’s body was rejecting the tea. Kilrain offered a draw, to which Sullivan growled, “No, you loafer” and continued battering the challenger. When Kilrain’s second ended the fight, the champion invited him to enter the ring and accept a similar thrashing.
After the fight the state of Mississippi offered a thousand-dollar bounty for Sullivan’s return, and the governor of New York had Sullivan extradited to stand trial on the charges of prizefighting and assault and battery. Sullivan beat the charges, but legal and travel expenses cost him more than he earned for beating Kilrain, and he vowed never to appear in another bareknuckle match. Nor would he have to, as this match cemented his legend forever. “Never, during even a Presidential election, has there been so much excitement as there is here now,” wrote The New York Times of Sullivan’s exploits.