MacKinnon has three times been a candidate for elected office. He ran for the Canadian House of Commons in the 1984 election in the riding of Cape Breton Highlands—Canso and twice for the Nova Scotia House of Assembly in the riding of Halifax Chebucto in the 1998 and 2003 elections, finishing second in all three cases.
He was a candidate for the leadership of the Nova Scotia Liberal Party in 2007. He finished fourth of four candidates on the first ballot. Forced to drop of the ballot, he endorsed Diana Whalen, who lost on the second and final ballot to Stephen McNeil.
- MacKinnon's announcement Lawyer MacKinnon joins race for N.S. Liberal leader, CBC.ca, January 19, 2007
- McNeil new N.S. Liberal leader, CBC.ca, April 28, 2007
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