The Chicago White Sox of the 1910's carried a team of players that looked better than most teams of the time at every position. Talent like that of Arnold Gandil at first base, Eddie Collins at second, Charles Risberg at short, George Weaver at third and Ray Schalk behind the plate. The outfield was quick and powerful with Shano Collins in right field, Happy Felsch playing center and "Shoeless" Joe Jackson in left. Eddie Cicotte was the team's ace starter and he was coming off the best year of his career, finishing with a 29-7 record. The only thing that could compare to the tremendous defensive talent the team possessed was their ability to hit for power. They had easily made it to the World Series, as most fans had expected. The only hurdle left for the team to overcome was defeating the Cincinnati Reds, who most people had written off before the series began. Actually, virtually everyone had assumed the Reds would lose earlier on, causing many to feel that the 1919 World Series was more of a formality than a contest.

Nonetheless, Major League attendance and salaries had both plummeted in recent years due to the effects of World War I. It is likely and feasible that the White Sox players began to get fed up with the low pay, which probably had more to do with the team's stingy owner, Charles Comiskey. Comiskey's fortune was largely due to the success of his players, yet player salaries didn't appear to reflect his gratitude. Despite arguably being the best team in the league at the time, most of the players continued to be paid below-average wages. It is rumored that their food allowance was well below the league average. The team bonus for reaching the World Series was reported to be a case of flat champagne. It was also said that when Ed Cicotte reached 29 wins, Comiskey benched him in order to avoid paying him a 30-win bonus. With these facts in mind, it is not difficult to see how the 1919 White Sox players fell prey to the temptations of gambling.

The first player to proposition the fix was first-baseman Arnold Gandil, who had been approached by a Washington area gambler named Joe Sullivan. Gandil offered to throw the series in exchange for $80,000, which he would then split amongst all the players involved. Sullivan agreed to this and recruited a rich gambler named Abe Rothstein and a former boxer named Abe Attel, who had been outcasted from the sport for fixing fights. The two gamblers agreed to pay $20,000 for each loss in the series, which would total $80,000 if the series were thrown. Gandil succeeded in recruiting seven of his teammates to participate in the scheme. Pitcher Eddie Cicotte, Claude "Lefty" Williams, shortstop Charles Risberg, third baseman George Weaver, outfielder Happy Felsch, "Shoeless" Joe Jackson (although his involvement is questionable) and a utility infielder named Fred McMullin who had to be included because he overheard the others talking of their plan. Thus, the conspiracy to undermine one of the highest-profile sporting events in the world was underway.

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