Richie had signed to play for the Tri-State League's Williamsport team in 1906. The Tri-State League was an "outlaw league" whose contracts were not respected by Major League Baseball, and Richie jumped his 1906 Williamsport contract to sign with the Phillies.
Richie was a gifted musician and minstrel show performer during his playing career. Minstrel entertainer George "Honey Boy" Evans practiced with the Phillies in spring training in 1908. Richie brought his instruments to Savannah, Georgia where the team trained, and he and Evans organized the other players into a minstrel troupe for evening entertainment.

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