In 2010, the Detroit Tigers drafted Holaday in the sixth round of the amateur draft. Prior to joining the Tigers, he was a member of the Horned Frogs at Texas Christian University. He has played for the Lakeland Flying Tigers, Erie Seawolves, and Toledo Mud Hens in the Tigers organization. He also played in the Dominican Winter League with the Tigres del Licey. He made his Major League debut in 2012.
Holaday played for two years at TCU, in his sophomore and junior years. Prior to playing at TCU, he spent one year playing North Central Texas College.