A 2009 graduate of the University of Hartford, Brady was the leadoff hitter and starting shortstop for four years. As a freshman he was selected to the America East Conference All-Rookie Team. While attending Northwest High School, where he was recently inducted into the Athletics Hall of Fame, Brady received County, State and Metropolitan Area recognition. He also earned a spot in the Brooks Robinson All-Star Game at Camden Yards and on Team Maryland. In the summers, Brady played locally for Post 295, the Gaithersburg Giants and the College Park Bombers of the Cal Ripken League. Brady has recently worked for the Baltimore Orioles in the Front Office, Spring Training Facility and AA Affiliate. In 2012, he was sponsored by the Orioles to attend the Scout Development Program in Phoenix, AZ.