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.
Considered a three-star recruit by Rivals.com, Calloway was ranked 55th among offensive tackle prospects in the nation.[1] He chose Iowa over Missouri, Kansas, and Arizona.
College career
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. He received an All-Big Ten Honorable Mention as a junior.[2]
In 2009, Calloway was listed at No. 13 on Rivals.com's preseason offensive tackle power ranking.[3] In June of that year, he was arrested and "charged with operating a vehicle while intoxicated" while driving a moped.[4]
Professional career
Pre-draft
Calloway was considered to be a late-round draft prospect in the 2010 NFL draft,[5][6] and drew comparisons to Marc Colombo.[7] According to NFL.com's Gil Brandt, "Calloway should be a solid pro starter" at right tackle in the NFL.[6]
He was selected by the Buffalo Bills in the seventh round (216th overall).[9] On June 8, 2010, Calloway signed a multi-year contract with the Bills. He was released on August 30, 2010.
^Buchanan, Olin; Dienhart, Tom; Fox, David; Huguenin, Mike; Megargee, Steve (August 22, 2009), "Preseason offensive tackle power rankings", Rivals.com, archived from the original on March 24, 2016, retrieved September 1, 2009