1903-12-22 (158lbs) Philadelphia Jack O’Brien w pts 15 Jack Twin Sullivan, Criterion Club, Boston, Massachusetts, USA

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1903-12-22 (158lbs) Philadelphia Jack O'Brien w pts 15 Jack Twin Sullivan, Criterion Club, Boston, Massachusetts, USA. Referee: Eugene Buckley. The Boston Post reported that this fight should be seen as involving the world title. After a few even rounds, O’Brien (158) took over, landing at the rate of three to one, and apart from the eighth through to the 13th when Sullivan (153) had some success he was on top all the way. At the end of the 14th Sullivan was in a bad way after O’Brien had concentrated on the body, but he somehow made it to the final bell.

Finally, on 27 January 1904, O’Brien was matched against his arch-rival, Tommy Ryan, at the National AC, Philadelphia, Pennsylvania. Although only a six-round no-decision fight, as it had been made at 158lbs the Chicago Tribune reported that Ryan’s right to the title was clearly at stake. After losing the press decision, Ryan was challenged to a fight at the weight by Bob Fitzsimmons, who claimed never to have resigned the middleweight title and that Ryan had been ducking him for years.

Several years later, O’Brien was quoted as saying that Ryan had tricked him by threatening to pull out of their Philadelphia six-rounder at the last moment unless he (O’Brien) deposited $1,000 to be forfeited in case Ryan was knocked out. According to O’Brien, rather than have the match called off he complied with Ryan’s wishes. Ignoring all challenges, more than a year passed by before it was rumoured that Ryan would defend the championship in a distance fight against O’Brien. But that fell through when Ryan insisted on 154lbs, a weight that O’Brien had difficulty in making. Early in 1906, it was reported that Ryan had posted a forfeit to meet O’Brien at 158lbs. However, with O’Brien looking to win the heavyweight crown and not interested in having further dealings with Ryan it came to nothing, and at the age of 36 and inactive for over a year Ryan handed his crown to his protégé, Hugo Kelly.