He tried out with several National Football League (NFL) teams prior to the 2014 season, including the Kansas City Chiefs, the Detroit Lions, and the Green Bay Packers.

In his second career start, Jennings also caught a 21 yard touchdown pass on a contested catch thrown into double coverage by receiver Austin Collie on a trick play against the Saskatchewan Roughriders.

[9] In March 2016, Lions GM and head coach Wally Buono announced that Jennings would enter training camp as the #1 quarterback on the depth chart (above veteran Lulay) and he hoped that Jennings would have earned that title by Week 1 of the 2016 regular season.

[14] Lulay suffered a concussion and separated shoulder in consecutive weeks, opening the door for Jennings to start for the remainder of the regular season.

[17] In late November, following the close of the season, Jennings informed the Lions that he would not be re-signing with the team, intending to become a free agent in February 2019.

[24] Jennings was demoted to third stringer, and closed out the 3-15 Redblacks' season with a three rushing touchdown performance, but his passing statistics for the year were the worst of his career.