On August 21, 1915, the Chicago White Sox acquire outfielder Joe Jackson from the Cleveland Indians for outfielders Larry Chappell and Robert Roth, pitcher Ed Klepfer, and over $31,000 in cash. Jackson will become a star for the White Sox but will later be banned from baseball for his alleged involvement in the “Black Sox” scandal of 1919.

With Jackson, his Cleveland days were numbered simply because owner Charles Somers was flirting with bankruptcy, and Jackson’s salary threatened the books. He was one of many players to earn a boost thanks to overtures from the Federal League, and another recruitment effort in 1915 put rumors of five-figure salaries in the newspapers. Somers, already struggling with the payroll on hand, decided that trading Jackson was his best option.

Charlie Comiskey, the White Sox owner had cash to spare, and so he sent Grabiner to Cleveland with a check and the instructions to top every other offer until Jackson came back with Grabiner to Chicago.

Harry Grabiner and Somers reached an agreement. Somers signed Joe to a three-year contract extension at his previous salary, then sent him to Chicago for $31,500 in cash and three players who collectively had cost the White Sox $34,000 to acquire. In terms of the total value of cash and players, this $65,500 transaction was the most expensive deal ever made in baseball up to that time.

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