Calloway was selected in the eighth round of the 1997 draft by the Arizona Diamondbacks.

Calloway spent the 2005 season with the Norfolk Tides, the Triple-A affiliate of the New York Mets and 2006 for the Pawtucket Red Sox, the Triple-A affiliate of the Boston Red Sox.

Prior to the 2007 season, he signed a minor league contract with the Philadelphia Phillies and was assigned to their Triple-A affiliate, the Ottawa Lynx.

Calloway attended James Lick High School and graduated in 1994.

This biographical article relating to an American baseball outfielder born in the 1970s is a stub.