An early portrait of Charles Albert Comiskey. Comiskey, who was born in Chicago on Aug. 15, 1859, first came to Dubuque in 1878. He founded the Chicago White Sox in 1900 and was inducted into the National Baseball Hall of Fame in 1939. Photo courtesy of the New York Public Library digital collection
July/Aug 2025 (Volume 17, Issue 4)
By John T. Pregler
The train rolled into the Illinois Central Railroad depot with Charles Albert Comiskey’s 1914 Chicago White Sox aboard. It was not the first time baseball’s “Old Roman” brought one of his professional baseball teams to his adopted hometown of Dubuque. Thirty-two years earlier Comiskey brought the 1882 St. Louis Brownstockings to Dubuque aboard the Flying Dutchman to attend his wedding to Nancy “Nan” Kelly at St. Raphael’s Cathedral.
Comiskey—who was born in Chicago on Aug. 15, 1859—first came to Dubuque in 1878 to work for his college friend, Ted Sullivan, who had a franchise with the Western News Agency selling newspapers, books and confectionary goods to travelers on the Illinois Central Railroad in and out of Dubuque. Comiskey also came to Dubuque to play baseball for Sullivan, who co-founded the Northwestern League. There Comiskey played for the Dubuque Red Stockings and the team won the league’s 1879 inaugural pennant. Comiskey met his best friend, Tom Loftus, on the Dubuque team.
Left: An 1886 Old Judge Cigarettes baseball card of player-manager and world champion Charles Comiskey of the St. Louis Browns. Right: An 1889 Old Judge Cigarettes baseball card of Tom Loftus, manager of the National Cleveland Spiders. Old Judge cards were produced by Goodwin & Co. in New York. Photos courtesy of John Pregler
Dubuque gained the baseball world’s attention on Aug. 4, 1879, when Cap Anson and the National League Chicago White Stockings—today’s Chicago Cubs organization—were in Dubuque to play an off-day exhibition game and were beaten 1-0 by the champions of the Northwestern League. Thirty-two years later, while being interviewed during a vaudeville stop in Dubuque, Anson pulled from a scrapbook the original box score from the 1879 game in Dubuque. Anson reminisced about the game and how Dubuque’s young pitcher, future Hall of Famer Charles “Old Hoss” Radbourn, was “a revelation” to Chicago with his “deceptive down shoot” pitch, the equivalent of a curveball.
Comiskey’s four years playing baseball in Dubuque while working for Sullivan at the railroad depot kept him in Dubuque year-round. During this time Comiskey met a young Dubuque girl and fell in love. On April 12, 1882, Comiskey married Nan Kelly. That same year the newlyweds took in Nan’s niece, Mable Fredericks, upon the death of her father and raised her as their own.
On Jan. 13, 1884, Charles A. Comiskey, Jr., was born. The first son born to the Comiskeys was not long for this world, however, as he died four days later. The Comiskeys buried their son in Mt. Olivet Cemetery in Key West. The following year a second son was born. John Louis “Lou” Comiskey would maintain ties to Dubuque his entire life.
Comiskey began his professional baseball career as a pitcher for Dubuque. But a weak arm combined with Radbourn as a starting pitcher forced Sullivan to move Comiskey to first base. Comiskey is recognized as revolutionizing first base play by being the first player to play off the base, an innovative change Comiskey developed while in Dubuque. Malcolm MacLean, sportswriter for the Chicago Evening Post, wrote in 1913 how “Comiskey revolutionized first base play in Dubuque freight yards.”
While practicing with Sullivan in the freight yards near the warehouses where the train merchants—including Sullivan and Comiskey—would replenish their supplies for sale on the next Illinois Central train arriving to or departing from Dubuque, Comiskey began to change how fielders played first base. Traditionally first basemen stood on the base awaiting a ball to be hit and thrown to them. Using a brick for first base Comiskey would practice playing away from the “base” while Sullivan hit ground balls towards him. Comiskey played further and further away from the base as Sullivan hit harder grounders to his right. It was at this time Comiskey came up with the idea of having the pitcher cover first base while the first baseman fielded the grounder. Sullivan and Comiskey would incorporate what they learned during practice into their on-field play in 1880 and 1881.
Charles Comiskey, owner of the Chicago White Sox, as seen at the opening of his $1 million Comiskey Park on the South Side of Chicago in 1910.
Comiskey was a fan favorite during his time playing in Dubuque. Surrounding towns like Dyersville, Manchester, Waterloo, Galena, Ill., and Prairie du Chien, Wis., enjoyed watching Sullivan, Loftus, Comiskey and the team roll into town on the steel rail and play their local boys for the honors of claiming victory on the field of play. Comiskey had experience playing baseball in Prairie du Chien prior to moving to Dubuque. John Comiskey had sent his son to St. John’s College in Prairie du Chien in 1873, where Comiskey played on the school team. The next year, Comiskey’s father sent him to St. Mary’s College in Kansas, where he met Sullivan. Comiskey was always a fan favorite in Dyersville, home to the Field of Dreams Movie Site. The Dyersville Commercial reported after a game in 1880, “Charlie Comiskey is a favorite with Dyersville audiences and was the recipient of great praise for his fine first base play.”
Comiskey left Dubuque for St. Louis in the spring of 1882 to start his Major League Baseball career playing for the St. Louis Browns of the American Association. A year later, Comiskey started his stint as a player/manager, guiding St. Louis to four straight American Association pennants and a world’s championship in 1886. He became the team’s full-time manager in 1885. Comiskey lived in St. Louis during the baseball season while Nan and the children remained in Dubuque. Comiskey would return to Dubuque during the offseason, or when he was injured. In 1887 Comiskey moved his wife and children to St. Louis to be with him during the season. The couple still wintered in Dubuque until 1891, when the family permanently made Chicago their home.
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