Jackson has also played for the Los Angeles Dodgers, Tampa Bay, Detroit, Arizona, the Chicago White Sox, St. Louis, Washington, the Chicago Cubs, Atlanta, Miami, San Diego, and Baltimore, in addition to the Blue Jays and A's. He finished with a record of 72-69 over two seasons with the Athletics and Blue Jays. He earned $1 million in 2007. In 2008, he went 9-3 with a 3.12 ERA over 110 innings pitched for the White Sox before being traded to the Phillies along with Jake Westbrook and Jason Frasor for Paul Konerko, Mark Buehrle, and Josh Donaldson. He ended up going 7-10 with a 4.14 ERA over 148 innings that year. After his time with the White Sox, Jackson joined the Toronto Blue Jays as a free agent and was expected to be their number three starter behind Halladay and Romero. However, after pitching only four innings in his first start for the Blue Jays, he was placed on the disabled list with shoulder inflammation. He returned in August but didn't regain his old form and was eventually released at the end of the season. After his release, he decided to retire from baseball. Overall, from 2004-2008, he made 80 appearances (all but one start) with a record of 36-30.