Drake was born in Indiana, Pennsylvania, and has worked in both Major Leagues since umpiring his first MLB game on September 3, 1999. Drake had previously worked in the Northwest, Midwest, Eastern, California and Pacific Coast leagues before reaching the MLB. Drake has also umpired winter baseball in the Dominican Republic, and officiated during the 2006 World Baseball Classic. Drake has worked MLB's All-Star Game (2013), Wild Card Game (2012, 2013, 2020), Division Series (2010, 2014), and League Championship Series (2012, 2013, 2015).