He served as alderman and mayor of Oshawa, and was a New Democratic Party member of the Legislative Assembly of Ontario from 1990 to 1995.
William Longworth, the founder of the group intended to run against Pilkey but in the end he was faced by a rookie, Mary Smith who jumped into the race at the last minute.
"[12] In early 1990 there were rumours that Pilkey would seek the nomination for the federal riding of Oshawa after NDP leader Ed Broadbent announced his retirement.
[15] The NDP won a majority government in this election under the leadership of Bob Rae, and Pilkey was appointed to cabinet on October 1, 1990, as Minister of Industry, Trade and Technology.
On July 31, 1991, Pilkey was named Solicitor General and Minister of Correctional Services and replaced by the more experienced Ed Philip.
[17] Pilkey was involved in a controversy with the Bell Cairn Training Centre for Prison Guards in Hamilton.
He was criticised for reacting too slowly to allegations of sexual assault and intimidation of female prison guards at the facility.
While the party had campaigned for the need for a 'common pause day' which Pilkey said was "not up for negotiation", court case decisions and increasing public demand led to a reversal of this policy.
The SIU which was set up by the previous Liberal Peterson government was supposed to handle investigations whenever police officers were involved in a shooting.
In the spring of 1991 a secret deal was worked out where some police force investigations were allowed to take precedence over the SIU's business.
[23] In 1992, two high-profile police shootings of black men in Toronto increased pressure on the government to react.
In addition police officers would not be allowed to draw their guns unless threatened by loss of life or serious bodily harm.
The most contentious change was that officers would now be required to fill out a report every time they drew their weapons in public.
Beginning in Toronto, Metro officers started a protest by refusing to issue tickets parking or for minor traffic violations.
[27] The NDP were defeated in the 1995 provincial election, and Pilkey lost the Oshawa riding to Progressive Conservative Jerry Ouellette by over 8,000 votes.