Toronto Blue Jays

Jackson signed with Toronto, and jumped to Triple-A in his first season in the Blue Jays organization. At the end of the year, the Blue Jays traded him along with Dave Bush and Gabe Gross to the Brewers for Lyle Overbay and Ty Taubenheim in December 2005.

Milwaukee Brewers

The Brewers started Jackson playing in Triple-A for the Nashville Sounds at the beginning of 2006. Jackson pitched well and had a 3.00 ERA for the first month and a half. The Brewers called Jackson up on June 2 to help with their current pitching problems. Jackson filled a major void left by the injured Tomo Ohka, replacing him in the starting lineup. He fared much better than expected and was sent back down to Triple-A to fine-tune his game, where he spent the entire 2007 season.

Cleveland Indians

On July 7, 2008, Jackson was part of the deal that sent Cy Young award winner CC Sabathia to Milwaukee for left fielder Matt LaPorta, pitcher Rob Bryson, and Michael Brantley. Jackson was recalled in August 2008 to fill the starting pitcher spot vacated by recently traded Paul Byrd.^[4]

Toronto Blue Jays

On January 9, 2010, Jackson was traded back to his first team, the Toronto Blue Jays, for a player to be named later.^[5]

Texas Rangers

Jackson was signed as free agent by the Texas Rangers on January 6, 2011.

Kansas City Royals

Jackson signed a minor league contract with the Kansas City Royals on February 11, 2013.

Washington Nationals

Jackson signed a minor league contract with the Washington Nationals on January 17, 2014. He was released on July 27.^[6]

On July 20, 2015, Jackson announced his retirement from baseball.^{[citation needed]}