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Callaspo was originally signed by the then-Anaheim Angels in 2001, playing for the Aguilas Cibaeñas of Dominican Summer League. In 2002, Callaspo batted .338 with 16 doubles, 10 triples, three home runs and 60 RBI in 70 games with the rookie-level Provo Angels, where he was voted by Baseball America as a Pioneer League All-Star and was named to Pioneer League All-Star team..
In 2003, Callaspo led the Midwest League with a .327 average and 38 doubles with the Cedar Rapids Kernels. Callaspo spent 2004 with the Double-A Arkansas Travelers, where he was selected for the Texas League All-Star game. Callaspo split 2005 with the Travelers and Triple-A Salt Lake Stingers. He again made the Texas League All-Star Game and was named to the Texas League Post-Season All-Star Team.
On February 28, 2006, the Angels traded Callaspo to the Arizona Diamondbacks in exchange for pitcher Jason Bulger. He began 2006 with the Triple-A Tucson Sidewinders. He was named the Diamondbacks' Minor League Player of the Year. Callaspo was called up to the Diamondbacks. He also split the 2007 season between Arizona and Tucson.
In 2009 Callaspo tied for the major league lead in errors by a second baseman, with 17, and had the lowest fielding percentage of any starting second baseman (.973).
Callaspo was arrested on Thursday, May 10, 2007 by Phoenix police for domestic violence at his home; the charges for Callaspo were later dropped. He was placed on the restricted list without pay the day after the arrest. The MLBPA filed a grievance on his behalf and he was reinstated within a week. Callaspo and his wife, Marianny Paola, remain together, and they have one child.