Everyone knew that no man could stand up to John L. Sullivan and swap punches with him. A devastating two-handed hitter, Sullivan had toured the country taking on all comers and had offered $1,000 to anyone who could stay four rounds. Drunk or sober, he had flattened 59 men in a row. Only a few were able to survive the first round, none the fourth. His only weakness was his fondness for the bottle—he used to drink bourbon out of steins—and for this reason his perfectly trained opponent, Jake Kilrain of Baltimore, was given an even chance to outlast him in a finish fight.
Kilrain was not a slugger but he could go distance and he was a good wrestler, which was useful in bare-knuckle fighting, where a fall could be almost as punishing as a knockdown blow. " Sullivan is no wrestler," said the New York World the day of the fight (July 8, 1889) and added with journalistic candor unknown today: "According to the history of all such drunkards as he, his legs ought to fail him after 20 minutes of fighting."
When the men came to scratch at 10 a.m. at Richburg, Miss, before a crowd of 3,000 fans, most of whom had come by train from New Orleans to the secret ring site (bare-fist fighting was illegal in all 38 states), the thermometer registered 100� in the shade. It was a test between two champions for $10,000 a side, winner take all. Sullivan, resplendent in green breeches and flesh-colored stockings, was champion by popular acclaim; Kilrain, by decree of Richard K. Fox, publisher of the Police Gazette, who ignored Sullivan's claim and awarded the Gazette's championship belt to his opponent. "I would not put Fox's belt around the neck of a bulldog," snorted the great John L.
From the start Kilrain pursued his battle plan by avoiding all toe-to-toe slugging and by sidestepping the rushes of the ever advancing Sullivan. These tactics drove Sullivan into a fury. "Why don't you fight? You're supposed to be the champ, ain't you?" bawled Sullivan in the fourth round, which lasted over 15 minutes. (Under the rules a round ended only when a man went down and could, therefore, last a few seconds or several minutes.) In the seventh round, when this photo was taken as the men clinched ( Sullivan on the left), Kilrain hooked to the head and brought a flow of blood from John L.'s ear. "First blood, Kilrain," announced Referee John Fitzpatrick and there was an exchange of bills among the sports. (Betting was always brisk on first blood and first knockdown.) Sullivan scored the first clean knockdown in the next round. As the fight wore on, both men were soaked in blood, their backs scorched crimson by the burning sun. There was no decisive turning point in the battle but after the 30th round it was evident that Sullivan was getting to his man. Jake was tiring, not Sullivan, who was now scoring all the knockdowns and most of the falls. But Kilrain kept on coming to scratch round after round although his eyes were glassy and his head rolled loose on his shoulders as if his neck were broken. In the 75th round a doctor said to Kilrain's seconds, "If you keep sending him out there, he'll die." That was enough. They tossed in the sponge and the fight was over. The last bare-knuckle fight in ring history had lasted two hours and 16 minutes. A new era of padded gloves and three-minute rounds under the modern Queens-berry rules soon replaced the old bare-fist brawlers. Sullivan lost his crown to Jim Corbett in a glove fight three years later. As for Kilrain, who was so near death at the end of the fight, he lived to be a pallbearer at Sullivan's funeral in 1918 and did not die until 1937 when he was 78.