He previously played in the Canadian Football League (CFL) and the National Football League (NFL), where he was picked in the third round of the 2013 NFL Draft by the Houston Texans. He played collegiate football at Louisiana State University, where he was named an All-American. In 2021, he will graduate from LSU. In 2012, Montgomery led all CFL quarterbacks with 3,990 passing yards while throwing 29 touchdowns against 14 interceptions. He also ran for four scores that season. Montgomery entered the NFL draft following his junior year at Louisiana State University. He was considered one of the best quarterback prospects in some time. During his career at LSU, he helped lead the Tigers to a 49-7 record over four seasons. As a freshman in 2010, he started 10 games before missing three games due to injury. That year, he completed 175 of 311 passes for 2,143 yards, 19 touchdowns, and five interceptions. As a sophomore in 2011, he started 12 games and finished the season with 2,767 passing yards, 20 touchdowns, and eight interceptions. As a junior in 2012, he started 13 games and finished the season with 3,990 passing yards, 29 touchdowns, and nine interceptions. Following his junior year, Montgomery decided to forgo his final season and enter the NFL draft. During his time at LSU, Montgomery never lost more than two games in a row.