Wilson had a combative streak and sometimes initiated fights with opposing players and fans. On June 22, 1928, a near-riot broke out in the ninth inning at Wrigley Field against the St. Louis Cardinals when Wilson jumped into the box seats to attack a heckling fan. An estimated 5,000 spectators swarmed the field before police could separate the combatants and restore order. The fan sued Wilson for $20,000, but a jury ruled in his favor. The following year he took offense at a remark by Cincinnati Reds pitcher Ray Kolp, and – upon reaching first base after hitting a single – he charged into the Reds dugout, punching Kolp several times before they could be separated. Later that evening at the train station, Wilson exchanged words and blows with Cincinnati player Pete Donohue. In late 1929 he signed a contract to fight Art Shires of the Chicago White Sox in a boxing match, but reneged after Cubs president William Veeck, Sr. enlisted Hack's wife Virginia to dissuade him, and then Shires lost a fight to George Trafton of the Chicago Bears. There was nothing to gain, Wilson said, by fighting a defeated boxer.