 A native of Montclair, New Jersey, Caldwell graduated from Montclair High School before spending a postgraduate year at the Lawrenceville School.After going undrafted in the 2010 NFL Draft, Caldwell signed with the Indianapolis Colts as an undrafted free agent on April 30, 2010.He started 13 games at strong safety during the 2011 Regular Season and made 67 tackles.