Bobby McCaffrey joined the Cal Ripken, Sr. Foundation in March of 2010. Prior to his time at the Foundation, he was a caddie for 11 years at Caves Valley Golf Club, a privately owned and managed golf club in Owings Mills, Maryland. Bobby played baseball in college for both Old Dominion University and Towson State University in the early 90’s. In his free time, he enjoys playing golf and spending time with his family. Bobby resides in Reisterstown with his wife, Amy, and daughters, Madison, Kelsey, and Kendall.