Prior to playing professionally, Chambers attended Pensacola High School where he was the star quarterback for his team.

He went on to attend Mississippi State University on a football scholarship before resuming his baseball career at Pensacola Junior College.

Hopefully, if the situation comes up again, I can produce again.”[3] Chambers was also noted for his contributions off the field to help spur the Cardinals on during their quest to win the Wild Card playoff berth.

With the Cardinals' playoff hopes looking much in doubt prior to the bottom of the ninth inning during their game on September 24, 2011, against arch-rival Chicago Cubs, Chambers was shown on the WGN television broadcast of the game taking it upon himself to encourage and excite the hometown fans to join him in cheering for the team prior to the start of the inning.

[4] Incredibly, the Cardinals began to rally, and Chambers himself was then inserted into the game as a pinch-runner, where he proceeded to score the winning run during a wild pitch.

[1] After splitting time between St. Louis and the team's minor league system in 2012 and 2013, Chambers was out-righted off the Cardinals roster on November 5, 2013, and elected free agency.

He played in 17 games with the Astros during Spring Training before being assigned to the Triple-A Oklahoma City RedHawks to begin 2014.

He was the team's Opening Day center-fielder and leadoff hitter, but injured himself on a slide, dislocating his left ring finger in the 4th inning, and he was placed on the disabled list.

On June 12, Chambers was traded to the Toronto Blue Jays for two minor leaguers, LHP Alejandro Solarte and 2B Will Dupont.