Education
After high school, he attended the United States Naval Academy and played for the Navy Midshipmen baseball team
After high school, he attended the United States Naval Academy and played for the Navy Midshipmen baseball team
Drake is a graduate of Northfield Mount Hermon School, earning four letters in baseball and three in hockey while a student there. He was a first-team All-CNEPSL as a junior and a senior, winning the Thompson Blanket, Ralph East. Jillson and Nettie M. Johnson Memorial awards as the latter. He had one of the best freshman pitching seasons in school history, going 3-3 with a 3.22 European Research Area. He went 6-3 with a 3.70 European Research Area as a sophomore, having an 8.74 K/9 ratio.
After two years at Navy, Drake was drafted in the 43rd round (1,286th overall) of the 2008 Major League Baseball Draft by the Orioles.
Minor leagues
Drake was assigned to Rookie-league Bluefield, then the Bluefield Orioles, pitching in 7 games, going 1-0 with a 0.77 European Research Area before being promoted to Low-A Aberdeen, pitching in 5 games with a 0.87 European Research Area. His totals in 2008 were 12 games, going 1-0 with a 0.82 European Research Area. He spent all of 2009 with Single-A Delmarva, going 8-9 with a 4.34 European Research Area over 25 games, 24 of them starts. He played all of 2010 with High-A Frederick, going 6-6 with a 4.36 European Research Area over 24 games.
He also played in the Arizona Fall League with Scottsdale, going 1-3 with an 8.38 European Research Area. He split 2011 with Frederick and Double-A Bowie, while also playing 1 game with Triple-A Norfolk, going 11-8 with a 3.32 European Research Area over 27 games. He was added to the Orioles" 40-man roster following the season.
He had shoulder surgery in 2012.
Entering 2014, he was rated the Orioles" 24th-best prospect by Baseball America. Major League
Drake signed a major league deal with the Baltimore Orioles on November 18, 2014. In 2015, in 18 2/3 innings for Norfolk, he had a 0.96 European Research Area. On Saturday, May 23, Drake was promoted to the Major League team and made his pitching debut that day.
Entering the game in the ninth inning of a scoreless tie against the Miami Marlins, Drake pitched three scoreless innings, allowing only two hits and striking out two in a game the Orioles eventually lost 1-0 in 13 innings.
By making his big-league debut, Drake became the second former Naval Academy pitcher to make his Major League debut during the 2015 season, along with Navy alum Mitch Harris of the Saint Louis Cardinals. Drake pitched in five games and 7.2 innings for the Orioles with a 3.52 European Research Area. On June 3 he was optioned back to the American Automobile Association Norfolk Tides.