Hawaii Winter Baseball
Bleich was selected in the First Round of the 2008 Major League Baseball Draft (44th overall) by the New York Yankees out of Stanford, and received a $700,000 signing bonus. "Baseball America" named him the Yankees' ninth-best prospect for 2010. He was named a Hawaii Winter Baseball post-season All-Star in 2008, pitching for the Waikiki BeachBoys, for whom he was 3–1 with a 1.77 ERA (2nd in the league among starters) in 7 starts. He then pitched in one game that season for the Staten Island Yankees of the Class A- New York-Penn League. In 2009, he pitched for the Tampa Yankees of the Class A+ Florida State League, and for the Trenton Thunder of the Class AA Eastern League, starting 27 games.