He played in Major League Baseball for the Pittsburgh Pirates, the New York Giants, and the Chicago White Sox.

His father worked as a foreman in a local steel mill, where the timekeepers misheard his last name, registering him as "Dickshot".

[11] When he was young, Dickshot's skull was fractured by older children throwing bottles in his backyard; he lost consciousness for three days and doctors inserted a metal plate in his head.

[14] He also worked in the steel mill with his father, and spent some of his free time watching the Chicago Cubs play at Wrigley Field.

[b] Dickshot began playing professional baseball in 1930 with the Dubuque Tigers of the Class D Mississippi Valley League.

[5][16] He did not play professionally in 1931, staying in Waukegan to work for his family in the steel mill during the Great Depression as his father had fallen ill.[15] He played semi-professional baseball locally in 1931,[17] and Nick Keller, the Illinois State Representative from Waukegan who also coached the team, scouted Dickshot for the Milwaukee Brewers of the Class AA American Association.

[28][29] Though he was batting .397, the Missions released him in late April to make room on their roster for Larry Bettencourt, and he signed with the Fort Worth Cats of the Texas League.

[33] A free agent heading into the 1934 season, Dickshot signed with Rock Island, now in the Class A Western League.

[34] At the end of May, Dickshot was released by Rock Island,[35] and he signed with Cedar Rapids Raiders, also of the Western League.

[41] Dickshot made the Pirates' Opening Day roster for the 1936 season as a reserve outfielder, as Lloyd Waner was recovering from pneumonia.

[43] With a May 15 deadline to reduce their roster size, Pittsburgh demoted Dickshot to the Buffalo Bisons of the International League.

[49] Traynor wanted Dickshot, who was right-handed, in the lineup for balance, as Jensen, Lloyd and Paul Waner, Gus Suhr, and Arky Vaughan all were left-handed batters.

[50] Dickshot struggled early in the season and was benched after he dropped a fly ball that cost the Pirates the game on May 23.

[64] Before the 1939 season began, Dickshot went unclaimed in waivers and the Bees sold him to the Jersey City Giants of the International League.

[67] He finished in third place in balloting for the International League Most Valuable Player Award, behind Mickey Witek and Estel Crabtree.

[73] After the 1940 season, the Giants sold Dickshot and Roy Joiner to the Hollywood Stars of the Pacific Coast League (PCL) for $15,000 and the rights to Joe Hoover.

[83] The next season, Dickshot batted .302 with 18 stolen bases in 130 games; he also tied Curtright for the team lead with four home runs.

[86] However, with major leaguers returning from military service at the end of World War II, the White Sox sold Dickshot back to Hollywood after the season, as they were reportedly looking for outfielders with better defensive skills.

[95] According to one story told about him, a fan in Little Rock asked to shake Dickshot's hand and approach the stands with him, telling him "I want my wife to see you, so she'll appreciate me".