John Joseph Killion, born on February 9, 1859 in Greenpoint, New York, changed his name to Jake Kilrain to hide his boxing habits from his parents. As a teenager, Kilrain worked in a mill, where he earned the reputation as the toughest fighter among all the workers. In 1883, Kilrain decided to pursue fighting professionally.
In the last bare knuckle heavyweight championship, fought in 1889, Kilrain faced John Sullivan, the defending champion. The match ended in the 76th round, with Sullivan the victor. After facing Sullivan, Kilrain fought gloved and enjoyed modest success. He defeated George Godfrey in 1891, by knockout in the 44th round. 1899 ushered in Kilrain’s retirement from the ring. He struck up a close friendship with Sullivan, his former rival. Kilrain passed away in 1937.