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Riddle grew up in Bedford, Texas and played baseball at Euless Trinity High School, where as a junior he was a co-pitcher of the year choice. He also was a two-time First Team All district selection as he went 7-4 with 100 strikeouts during his senior season at Trinity High. He went on to play college baseball at the University of Texas-Arlington and North Central Texas College. After college, Riddle went on to play two seasons in the St Louis Cardinal organization. Began season with Chico Outlaws going 1-2, 7.13. He was signed as a non-drafted free agent by the Cardinals in 2007
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