Joseph J. Sullivan
Joseph "Sport" Sullivan was one of the central figures in the Black Sox Scandal. A Boston, MA-based gambler, he kept a front as a regular businessman working in real estate, but was in fact running a "bucket shop" designed to bilk unwary investors before turning to sports gambling. As early as the first modern World Series, played in 1903 and involving the local Boston Americans, he was reputed to have made bets as large as $1,000. He was later accused of fixing boxing matches and was arrested in 1906 for gambling at the Boston Beaneaters' ballpark.
More arrests for gambling followed in 1911, 1913 and 1914, but he was able to pay the fines and resume his profession, which was likely quite lucrative as the occasional brushes with the law were just part of the cost of doing business. By then he had made a reputation throughout the East Coast as a baseball expert and someone to be consulted on the matters of baseball betting and prognostication.
In the Fall of 1919, he apparently met Chick Gandil and Eddie Cicotte of the Chicago White Sox at the Buckminster Hotel in Boston to talk about the upcoming World Series. Sullivan apparently already knew both men well and approached them about a plot to fix the Series, at which point Gandil assured him that it was something that had been done in the past. They met again at the Hotel Lenox a few days later, at which point Gandil and Cicotte were asked to line up enough players to make the fix effective. The whole group met again in New York, NY on September 21st, the players asking for $80,000 ($10,000 each) to throw the Series. Sullivan then approached New York underworld kingpin Arnold Rothstein to put up the money required. Sullivan and his associates then placed huge bets on the outcome of the Series, totaling $30,000.
The plan began to unravel when Sullivan tried to short-change the players (who had wanted the money upfront). The White Sox eventually lost the Series to the underdog Cincinnati Reds, but the gamblers did not all make money, as those who bet on individual games lost big when some of the plotting players, not seeing the money, decided to renege on their pledge and won some of the later games. Eventually, Rothstein lost patience, and sent a hitman to threaten Game 8 starting pitcher Lefty Williams if he did not lose the clinching game, as the story goes, which Williams promptly did. While rumor has it that Sullivan made out like a bandit thanks to the fix, he always denied it, claiming that if that had been the case, he would have retired to a mansion (which he did not do).
When an investigation was launched into the shenanigans that had taken place, Sullivan claimed not to have done anything other than place large bets on the games. He seemed to have obtained Rothstein's protection, as authorities were not really keen on interrogating him. He was never summoned to Chicago, IL to testify before the Grand Jury. He was eventually charged with a conspiracy to defraud, but the charges against all of the accused were quashed at the subsequent trial. While some minor characters in the conspiracy eventually told their side of the story to researchers such as Eliot Asinof, it was not the case to Sullivan, who it seems was never questioned by anyone trying to get at the truth of what exactly happened. His public profile faded noticeably after the trial, and he was no longer tolerated around baseball grounds. He seemed to have concentrated his later activities on boxing.