Jackson played 263 games in the NHL for the Toronto Maple Leafs, New York Rangers, Quebec Nordiques, and Chicago Blackhawks.

When Ferguson was fired on January 22, 2008, Jackson remained as the team's assistant general manager under Cliff Fletcher.

On September 12, 2008, Jackson was appointed the new general manager and governor of the Toronto Marlies, the American Hockey League farm club of the Maple Leafs.

In March 2010, months after Brian Burke became the team's GM and president, Jackson left his position with the Leafs.

[2] Jackson stepped down as interim general manager on July 24, with the Oilers' hiring of Stan Bowman.