[1] Henry attended Trinity Catholic High School in Ocala, Florida, where he played both football and baseball, and competed in track & field.

Henry went on to start 5 games for the season, with a 3-game set back, which he injured a finger on his throwing hand.

With backup Marve still recovering from his own ACL injury, Caleb TerBush took over as the starting quarterback in their place.

[11] He was a two-time all-county selection in football, and led his team to state finals his senior season.

As a freshman and sophomore, he played free safety and wide receiver, while John Brantley was at quarterback.

[12][13] In 2009, Henry sat for the season using his redshirt to learn head coach Danny Hope's offense.

He was also the first Purdue quarterback in school history to lead the team in both rushing and passing yardage in a season.

With backup Marve still recovering from his own ACL injury, Caleb TerBush took over as the starting quarterback in their place.

[19] After not playing in the Notre Dame game, Henry was named the backup against Eastern Michigan, as Marve was sidelined with his third ACL tear.

With Marve and TerBush out of the mix due to graduation, and new Purdue head coach Darrell Hazell, Henry entered fall camp with the Boilermakers competing with freshmen Danny Etling and Austin Appleby for Purdue's starting quarterback spot.

Two weeks before the regular season opener at Cincinnati, Hazell named Henry Purdue's starting quarterback.