Born in 1859, and of Irish ancestry, Comiskey began his career in the old American Association with Chris Von Der Ahes St.Louis Browns, playing for $90 a month. He helped to revolutionize 1st base by ranging far off the bag to off base hits. By his second season with St. Louis, Comiskey, at age 23, was the playing manager, and every year from 1885 to 1888 the Browns won the American Association pennant. In 1890 Comiskey jumped to the Players League, but when it collapsed after one season, he returned to St. Louis. The AA also folded at the end of the 1891 season, and Comiskey moved on to manage John T. Brush's Cincinnati club.
There he met Ban Johnson. Johnson soon became president of the Western League, and in 1894 Comiskey became the owner of its Sioux City franchise, which he quickly transferred to St. Paul. In 1901 the Western League became the American League, and St. Paul was dropped. In its stead Comiskey was given the new Chicago franchise in the AL, and he dubbed his team the White Stockings, in honor of the Windy City's original National League club. In 1910 Comiskey constructed Comiskey Park at a cost of $750,000.
Comiskey had a very generous side. Any reputable Chicago organization could use the park free of charge. Comiskey would invite a hundred guests to his Wisconsin estate, pay the Notre Dame tuition for the sons of pitcher Ed Walsh and catcher Billy Sullivan, and even tithe his revenues to the Red Cross during World War I.
With his players, however, he was an absolute tightwad. The White Sox played in the league's filthiest uniforms; Comiskey had given orders to cut down on laundry bills. Most clubs received $4 per day for meals; Comiskey gave his men $3. Stars such as outfielders Joe Jackson and Happy Felsch, pitchers Lefty Williams and Ed Cicotte, and infielder Buck Weaver were grievously underpaid. In 1917 Comiskey promised the club a bonus for winning the pennant, and all he delivered was a case of cheap champagne at the team's victory party.
More than anyone person, more so than the gamblers and the players themselves, Comiskey was responsible for the 1919 Black Sox scandal. If only he had open the coffers and given his players a decent minimum wage, there most likely would never have been a scandal and no one would have ever heard of "The Black Sox. If only! It figures that Comiskey would blame Ban Johnson for the scandal for allowing the series to continue after rumors of a fix came out.
Comiskey died in 1931, at age 72, at his Wisconsin summer home. He was elected to the Baseball Hall Of Fame by the Committee on Baseball Veterans in 1939.