Crowe attended Westview High School, and was selected by the Oakland Athletics in the 20th round of the 2002 Major League Baseball Draft.

[5] Crowe was named to the 2006 Carolina League All-Star game, but was unable to participate due to injury.

After initially being optioned to the minors on March 28, 2009, Crowe was recalled at the end of spring training due to an injury to David Dellucci and was part of the Indians' Opening Day roster.

Crowe made 122 appearances for the Indians in 2010, slashing .251/.302/.333 with two home runs, 36 RBI, and 20 stolen bases.

Crowe played in 38 games for Columbus in 2012, hitting .250/.336/.386 with three home runs, 12 RBI, and eight stolen bases.

[15] In 66 games for the Triple–A Toledo Mud Hens, he slashed .240/.291/.349 with four home runs, 26 RBI, and eight stolen bases.

At his sentencing, his attorneys argued that he suffered from opioid addiction and mental illness which contributed to his conduct.