Dempsey, a Frontier League All-Star in 2008 returns to Washington after hitting .310 last season while leading the league in games played (96), doubles (31), and RBI (88). He finished second in extra base hits (52) and fourth in total bases (203), walks (67) and on base percentage (.422). His 96 games and 31 doubles is a Wild Things single season record, and his 88 RBI tied for the team record with Mike Arbinger (2005).

Dempsey was originally the Philadelphia Phillies 21st round selection in the 2006 June Amateur Draft from Winthrop University. He made his professional debut at Batavia (NY) of the Class A New York-Penn League that season. With the Muckdogs, he batted .262 with a team high 17 doubles and seven homeruns in 58 games. He batted .318 in 29 games in August with three homeruns and 25 RBI. He had a 13 game hitting streak from August 14 through August 27 when he batted .415 with five doubles, three home runs, and 15 RBI. He was a teammate of Wild Things RHP Kevin Salmon with Batavia.

During his senior season at Winthrop, he was named a First Team All-American by rivals.com, and a second team All-American by Baseball America Magazine. He led the team with a .403 batting average, which was second in the Big South Conference. Dempsey also set a Big South Conference single-season record for hits with 100, and a Winthrop single-season record for doubles (28) and RBI (78). He completed his career as the school’s all-time leader in doubles with 78, while ranking in the top five for hits, runs scored, home runs and total bases. He was name an All-Conference selection in 2004, 2005 and 2006.