Prior to high school, Redman played little league baseball at Duncanville, Alabama against teams from Taylorville and Moundville.

Redman was designated for assignment on November 21, 2005, by the Pittsburgh Pirates after he had become expendable with the promotions of Nate McLouth and Chris Duffy to the major leagues.

While spending all of the 2006 season in the minor leagues with the Detroit Tigers and Houston Astros organizations, he had a batting average of .268 over 106 games.

Redman batted .300, with 2 home runs, and 25 stolen bases in 79 games for their Triple-A Norfolk Tides, before having his contract purchased by the O's, on August 9.

Redman joined the APBL Newark Bears in 2009 as their starting center fielder and leadoff hitter.