At the University at Buffalo, Willy started each of his four seasons, including eight games as a true freshman. In 2008, he took Buffalo to their first MAC Championship Game, where they upset heavily favored and previously undefeated Ball State Cardinals led by Nate Davis. Prior to the 2009 NFL Draft, he was invited to the 2009 NFL Combine and was considered a potential late-round draft choice.
Willy was the most prolific passer in Buffalo football history. As a four-year starter, he set school records for completions (849), attempts (1,322), passing yards (8,748), touchdowns (52), total offense (8,639), and completion percentage (64.2). During the final 20 games of his college career, Willy threw 36 touchdown passes and only six interceptions.
Willy was signed to the Indianapolis Colts practice squad on December 9, 2009. He was promoted to the active roster on December 26. He was waived on December 29 and re-signed to the practice squad. He was signed to a future contract on February 11, 2010. He was released by the Colts in July 2010.
He made his UFL debut on October 23 in the place of injured Locos starting QB, Tim Rattay. He completed 18 of 29 passes that day for 191 yards and a touchdown. The Locos won the game against the Hartford Colonials, 24-21.
On February 28, 2012, it was announced that Willy had signed with the Saskatchewan Roughriders. Willy made his first CFL start on September 16, 2012, in Montreal against the Montreal Alouettes. He completed 22-of-35 passes for 225 yards and a touchdown with two interceptions in a losing effort. Willy earned his first CFL win as a starter on July 27, 2013, against the Hamilton Tiger-Cats where he completed 14 of 25 pass attempts for 269 yards with three touchdowns and zero interceptions in relief of the injured Darian Durant. In two seasons with the Roughriders, Willy was utilized in a backup role. He dressed in all 36 games, and started four, passing for 1,182 yards with nine touchdowns and five interceptions.
Willy leaves the field after a close game at McMahon Stadium in Calgary on July 18, 2015.
On February 6, 2014, Willy was traded to the Blue Bombers for non-import wide receiver Jade Etienne. In his first year as a starter Willy lead the Bombers to a record of 7 wins and 11 losses. He played in 17 of the 18 regular season games. In the spring of 2015 Willy and the Blue bombers agreed to a contract extension through the 2017 season. In week 7 of the 2015 CFL season Willy left the game with a right knee injury: Two days later it was announced that Willy suffered a tibial plateau fracture and partial tear of the posterior cruciate ligament. He is expected to miss 6 to 8 weeks, possibly longer.
^McKissic, Rodney. "Willy bowls over UB coaches", The Buffalo News, August 2, 2008. Accessed July 27, 2009. "Willy had worked under a different offensive coordinator and offensive system for four straight seasons, dating from his senior season at Randolph High School in New Jersey, and said he is thrilled because he spent a second straight off-season studying under Gill and quarterbacks coach Danny Barrett."