On February 2, 2011 Clemson University named Caldwell offensive line coach to replace the retiring Brad Scott.

Caldwell, a Pageland, South Carolina native, attended Furman University where he played football and was a three-year letterman.

During Caldwell's years as an assistant, Vanderbilt won road games at Arkansas (2005), Tennessee (2005), Georgia (2006), South Carolina (2007), Ole Miss (2008) and Kentucky (2008).

On August 2, 2010, Vanderbilt Vice-Chancellor David Williams announced that the "interim" tag would be dropped from Caldwell's title, and that they had agreed to a new contract.

[4] Caldwell was a hit in his first public appearance at SEC Media Days, and has been a popular guest among sports talk shows.

[6] On September 18, 2010, following close home losses to Northwestern and LSU, Caldwell picked up his first ever win as a head coach, as the Vanderbilt Commodores defeated the Ole Miss Rebels 28-14 in Oxford, MS.

However, after a lot of reflection, I’ve realized it is time for me to step aside and let someone else pick up the hard work and efforts of our staff.”[8] # denotes interim/acting head coach