[1] Leak received national attention as an 8th grader in 1998 when Wake Forest coach Jim Caldwell, who had just signed his older brother, C. J., offered him a college football scholarship.

[1] In four years as the Patriots' starting quarterback, Leak led his team to three consecutive North Carolina 4-A state championships.

He started all of Florida's games, including a memorable school record-tying six-touchdown performance against the South Carolina Gamecocks.

However, following a disappointing loss to the unranked Mississippi State Bulldogs and an on-campus confrontation with fraternity members, head coach Ron Zook was fired.

Heading into his 2005 junior season, Leak had to learn his third offensive scheme in as many years, but was touted as a possible Heisman Trophy candidate.

Leak won his first five games, including a big win over the SEC East rival Tennessee Volunteers, but struggled in the option portion of the Meyer's offense.

Before the beginning of his 2006 senior season, there was speculation that Leak might not be the Gators' starting quarterback due to the emergence of talented freshman Tim Tebow.

Preseason analysis projected that Florida would have the hardest schedule in the country, including back-to-back games against Tennessee, Kentucky, Alabama, LSU, Auburn and Georgia.

Leak led the Florida Gators to their second consensus national championship with a 41–14 victory over the Ohio State Buckeyes on January 8, 2007, taking home the offensive Most Valuable Player (MVP) award for the game.

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.

[8] However, Leak only saw playtime during the final game of the preseason, where he completed eleven of sixteen passes for 88 yards, an interception and a touchdown.

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.

On September 26, 2011, Leak signed with the ArenaBowl XXIV champion Jacksonville Sharks, replacing star quarterback Aaron Garcia, who joined the San Antonio Talons for the 2012 Arena Football League season.

After it was announced that Garcia's former backup, Omar Jacobs, would start the next game, Leak was suspended after skipping the following team practice.

He was hired as the head coach of the football team at Edgewater High School in Orlando, Florida, in February 2016.