Before entering politics, he was the Chief Executive Officer of the Metropolitan Hamilton Real Estate Board, and also worked for the Halton Housing Authority from 1975 to 1980.
In late 1985, Jackson supported Alan Pope's unsuccessful bid to replace Miller as party leader.
The Progressive Conservatives returned to power in the 1995 provincial election, and Jackson was re-elected in Burlington South with over 70% of the popular vote.
[5] He was made a Minister without Portfolio in the government of Mike Harris on June 26, 1995, with responsibility for the Workers Compensation Board.
[7] He was finally given a full portfolio on July 27, 1998, being made Ontario Minister of Long-Term Care and Seniors.
[10] He was forced to resign on October 2, 2002 due to a controversy over his practice of billing the government for steak dinners and hotel stays.