Leak was listed on the SEC Academic Honor Roll each year he attended Florida, and was a finalist for the Draddy Trophy, also known as the "Academic Heisman" for college football players. He graduated from the University of Florida with a bachelor's degree in sociology, with honors, in December 2006, and was a keynote speaker during the graduation ceremony. Leak is remembered for volunteering with children in the Goodwill Gators Program, encouraging them to put school first and avoid drug use. At home in Charlotte, North Carolina, he also worked with the Boys and Girls Club and the Steele Creek Youth Athletic Association, served as an inspirational speaker with the Fellowship of Christian Athletes, and spoke at area middle schools encouraging students to stay focused on their goals. Leak was not selected during the 2007 NFL Draft. The Chicago Bears signed him immediately after the draft. He spent the summer of 2007 working with the team, and training under former Gator quarterback predecessor Rex Grossman. However, Leak only saw playtime during the final game of the preseason, where he completed eleven of sixteen passes for eighty-eight yards, an interception and a touchdown. He was eventually cut from the Bears roster on September 16, 2007. For the 2008 season, Leak tried out with the Kansas City Chiefs. In November 2007, Leak announced his intentions to play for Team Florida in the All American Football League. He was later drafted in the 6th round by Team Florida. Lacking start-up capital and with low ticket sales, the AAFL's first season was postponed until 2009 (and later canceled). Leak, like all AAFL players, was released from his contract. On June 3, 2008, Leak signed with the Hamilton Tiger-Cats of the Canadian Football League. He was claimed by the Montreal Alouettes on June 9 after being released a day earlier. With backup quarterback Adrian McPherson injured, Leak was on the active roster for the August 21, 2009 match against the Saskatchewan Roughriders, in which he threw his first CFL touchdown pass on his first play. The Montreal Alouettes went on to win the Grey Cup in 2009. On August 19, 2010, in a game against the Winnipeg Blue Bombers, Montreal starting quarterback, Anthony Calvillo, got taken out with an injury which gave way to Leak to finish off the game. Leak would lead the Alouettes to a 39-17 win over the Bombers. Leak made his first CFL start at quarterback on September 3, 2010 against the BC Lions.