Wilson returned to Martinsburg where he opened a pool hall, but encountered financial problems due to a failed sporting goods business venture, and then a rancorous divorce from Virginia. By 1938 he was working as a bartender near Brooklyn's Ebbets Field where he sang for drinks, but had to quit when customers became too abusive. A night club venture in suburban Chicago was another financial failure. In 1944 he took a job as a good will ambassador for a professional basketball team in Washington, D.C., where he lamented that fans remembered his two dropped fly balls in the 1929 World Series far more vividly than his 56 home runs and 191 RBIs in 1930. Unable to find work in professional baseball, he moved to Baltimore where he worked as a tool checker in an airplane manufacturing plant and later as a laborer for the City of Baltimore. When municipal authorities realized who he was, he was made the manager of a Baltimore public swimming pool.