He was selected by the Buffalo Bills in the seventh round of the 2010 NFL draft out of the University of Iowa.

Considered a three-star recruit by Rivals.com, Calloway was ranked 55th among offensive tackle prospects in the nation.

After redshirting his initial year at Iowa, Calloway saw limited action as a back-up at left guard in 2006.

[3] In June of that year, he was arrested and "charged with operating a vehicle while intoxicated" while driving a moped.

On July 2, 2016, Calloway was jogging alongside a set of railroad tracks and was hit from behind by a train, killing him.