Dave Obstgarten has been playing ball for his entire life, including the University of Maryland (both Division 1 and Club teams) between 1995-1998 and the Erie Seawolves. During his collegiate career as a pitcher, he was offered minor league contracts from the Montreal Expos in 1996 and the Detroit Tigers in 1998. After making the tough decision to turn them down and follow a different path, he coached the University of Maryland Club baseball team between 1998-2003.

Since then, he has focused on sharing his passion for the game with younger players, having coached many high level youth travel baseball programs, including the BCC Gators (12U) and the BCC Bombers (11U). He now tries to instill a love of the game on a daily basis as an athletic teacher in Montgomery County , Maryland.