Dowling was the oldest of five children in an
Irish Catholic family in St. Louis. His paternal grandfather emigrated from Ireland in the mid-1800s and opened a railroad construction company, which his father also managed. Both his father and mother, Anastasia Cullinane, were observant Catholics. Dowling was a student at Holy Name School before attending St. Louis University High School. He attended St. Mary's College in Kansas, and played baseball semi-professionally as well as in school. He tried out for both the
St. Louis Browns and the
Boston Red Sox, but neither hired him. Dowling initially studied journalism; he reported for the
St. Louis Globe-Democrat for a year before joining the
U.S. Army in
World War I. He studied for a year at
Medill School of Journalism at
Northwest University. Dowling also had training as a
genealogist, and was an advocate of
civil rights. In 1957, the 100th anniversary of the
Dred Scott court case, Dowling led an effort to locate Scott's previously unmarked grave. Dowling raised funds for a modest headstone, saying, "[I]f someone some day wants to put up a better monument it will at least be known where
Dred Scott lies." == Alcoholics Anonymous ==