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Richard was awarded Indiana's Mr. Football and Mr. Baseball his senior year at McCutcheon High School.
Richard accepted a scholarship to play football and baseball at the University of Michigan in the fall of 2003.
Richard was redshirted for the Wolverines football team his freshman year. In 2004, he battled for the starting spot on the team, but lost out to Chad Henne. Richard was the Wolverine's #2 quarterback that season, but he saw limited action, mostly in blowout wins over Miami (Ohio), Indiana, and Northwestern. Richard appeared in 4 total games for the Wolverines in 2004, only attempting 15 passes for 8 completions and 52 total yards.
The following spring, Richard joined the Wolverines baseball team and pitched well. In his one season in Ann Arbor, Richard pitched 21 games, mostly as a reliever and compiled a 0-1 record with a 2.43 ERA, a 1.20 WHIP, and 27 K's in 33.1 IP, good for a 7.29 K/9 innings ratio. The Wolverines were 42-19 that season and finished 4th in the Big 10 with a 17-12 conference record. They were the 3rd seed in the Atlanta Regional of the College Baseball Tournament, but were eliminated in the 2nd round of the Regionals, losing both games to South Carolina by 1 run. After starting his baseball career with moderate success, Richard dropped his football scholarship at Michigan and focused on baseball full-time.
The White Sox selected Richard in the 8th round of the 2005 Major League Baseball Draft. He was the 2nd player from Michigan drafted, the first being Chris Getz, also selected by the Sox in the 4th round.
After playing for the Rookie-level Great Falls White Sox and Class-A Kannapolis Intimidators in 2005, the Intimidators and Class-A Advanced Winston-Salem Warthogs in 2006, the Warthogs in 2007 and the Class-AA Birmingham Barons and Class-AAA Charlotte Knights in 2008, Richard made his major league debut with the White Sox on July 23, 2008.
Richard made the White Sox opening day roster in 2009.