A native of Broken Arrow, Oklahoma, Bailey attended Broken Arrow Senior High School, where he anchored the offensive line for three straight season and was regarded a three-star recruit by Rivals.com.

In his redshirt sophomore season at Arkansas, Bailey was a Second-team All-SEC selection.

In December 2012, Bailey announced his decision to forgo his final year of eligibility, entering the 2013 NFL draft.

He signed with Morgan Advisory Group, and began his preparations for the NFL Combine workouts in Arizona.

[7] He was suspended two games on December 15, 2016, as a result of a driving under the influence arrest in September [8] On April 20, 2017, he was released by the Browns.