American boxer (1859–1937) who was named Heavyweight Champion of the World in 1887—“unofficially,” by the National Police Gazette. On July 8, 1889, the most celebrated bout of the bare-knuckle age took place in Richburg, Mississippi, in front of 3,000 eager spectators. Fighting under the bare-knuckles London Rules—the last official instance prior to the adoption of the Queensberry Rules—Kilrain and John L. Sullivan entered the ring to fight one of the bloodiest and longest fights in boxing history. Two hours and sixteen minutes later, after seventy-five rounds of animalistic combat, Sullivan emerged as the undisputed “Champion of the America,” a title he had lost to Charley Mitchell in March of the previous year. Kilrain and Sullivan later became good friends, and Kilrain served as an usher at Sullivan’s funeral in 1918. ALS signed “Jake,” four pages on two adjoining sheets, 4.5 x 7, April 22, 1889. Kilrain writes to “Murf,” quite possibly boxer Johnny Murphy. In full: “A line to you hoping it will find you all right. I see by the papers here you are going to fight Call [sic] McCarthy of Jersey. I wish you the best of good luck old boy get well and keep cool now is your chance to gain a big name as he is a good man with a big name. My trip will be a failure as I must come home now and we can’t do anything in the way of showing we would have had a lot of money at the Smith Mitchell show but as you know Smith hurt his foot and he is still laid up with it. I am coming home about the last week of May. We could do good business here if we had time to arrange some big shows. If I beat J. L. I am going to Australia. How is Jim Keenan and all the boys. Give him my kindest regards. I was very sorry to hear of Jim’s sickness I hope he is well by this time. Their [sic] is a big competition here this week everything else is quite [sic]. With best wishes to you and all your family and hoping you will win in a canter.” In fine condition, mild soiling, and a few brushes and stray ink marks to final page. Auction LOA Steve Grad/PSA/DNA and R&R COA.