O'Connor was involved in a scandal in 1910 when, as player-manager of the St. Louis Browns, he attempted to help Nap Lajoie win the batting title over Ty Cobb.

He tried to help Nap Lajoie win the batting title and the associated 1910 Chalmers Award over Ty Cobb in the last two games of the season, a doubleheader at Sportsman's Park.

O'Connor and coach Harry Howell tried to bribe the official scorer, a woman, to change the call to a hit, offering to buy her a new wardrobe.

The resulting outcry triggered an investigation by American League president Ban Johnson, who declared Cobb the rightful winner of the batting title (though Chalmers awarded cars to both players).

At his insistence, Browns' owner Robert Hedges fired both O'Connor and Howell and released them as players; both men were informally banned from baseball for life.