As a military dependant, Calloway attended three high schools in four years. He graduated from Belleville East High School in Belleville, Illinois, where he was an all-city and all-conference tackle as a senior, and also played tight end and primarily defensive tackle as a junior.
He was drafted by the Buffalo Bills in the seventh round of the 2010 NFL Draft out of the University of Iowa. Calloway was considered to be a late-round draft prospect in the 2010 NFL Draft. Considered a three-star recruit by Rivals.com, Calloway was ranked 55th among offensive tackle prospects in the nation.
He chose Iowa over Missouri, Kansas, and Arizona.
After redshirting his initial year at Iowa, Calloway saw limited action as a back-up at left guard in 2006. In 2007, he became the starting left tackle, but was replaced with Bryan Bulaga and moved to right tackle in 2008.
In 2009, Calloway was listed at Number. 13 on Rivals.com′s preseason offensive tackle power ranking.
In June of that year, he was arrested and "charged with operating a vehicle while intoxicated" while driving a moped.
On June 8, 2010 Calloway signed a multi-year contract with the Buffalo Bills. He was released on August 30, 2010. 2010 NFL Draft
Calloway ranks among the best offensive tackles in his class, and draws comparisons to Marc Colombo.
According to NFL.com"s Gil Brandt, "Calloway should be a solid pro starter" at right tackle in the NFL. He was drafted by the Buffalo Bills in the seventh round (216th overall).
Hartford Colonials
Calloway signed to play 2011 for the United Football League"s Hartford Colonials. Baltimore Ravens
On August 9, 2011, Calloway signed with the Baltimore Ravens, but was waived on August 21.
He has also been a member of the Hartford Colonials and Baltimore Ravens.
