[4][5] Etobicoke was the only area in Toronto not affected by the 2009 garbage strike, with the sick day accumulation plan being one of the unresolved issues between the city and CUPE.

With the position of Mayor of Etobicoke abolished, Holyday ran and was elected to the new Toronto City Council representing Ward 4 (Markland Centennial).

For example, in 2008 Holyday proposed that taxpayers' money could be saved if Toronto city councillors reduced their office expenses, kept better track of business mileage, adopted more frugal newsletters, stopped donating to community groups and sports teams in their wards, and had to justify restaurant meals.

He once criticized plans to close certain streets in downtown Toronto for a "car-free day", saying that that would have a negative impact on businesses.

In 1987, Holyday ran for the Legislative Assembly of Ontario as a Progressive Conservative candidate in the 1987 provincial election, but lost to Liberal Linda LeBourdais by over 6,000 votes.

In July 2013, Holyday again ran as a Progressive Conservative candidate in the August 1, 2013 by-election to replace retiring Liberal Laurel Broten in the riding of Etobicoke—Lakeshore.

Although he once argued that councillors who run for higher office should immediately resign from council, he instead elected to take a leave of absence without pay.