He was selected by the Pittsburgh Pirates in the 2004 MLB draft and traded to the Atlanta Braves four years later, but never appeared with either team.

He was in his fourth season with the Braves' triple-A affiliate in Gwinnett before being called up for the first time in his career on June 17, 2012.

He gave up a leadoff home run to Brett Jackson in the second inning to give the Cubs an early lead.

After giving up consecutive RBI hits to Anthony Rizzo and Starlin Castro in the top of the fourth inning, he was relieved by Alfredo Simon.

[14] On March 22, 2013, Redmond was claimed by the Toronto Blue Jays, and immediately optioned to the Triple-A Buffalo Bisons.

[19] Redmond, starting on July 7 against the Minnesota Twins, pitched 5 innings and gave up just 1 hit, a two-run home run to Aaron Hicks.

[20] Redmond established career-highs in innings pitched and strikeouts with 6 and 10 respectively, in a game against the Houston Astros on July 28, 2013.

On May 31, 2014, Redmond earned his first MLB save, pitching 3 innings in relief of Marcus Stroman's first career start.

After 2 appearances, in which he posted a 16.62 ERA with 5 walks and 4 strikeouts, Redmond was designated for assignment on April 16.