He was the last mayor of the former city of Etobicoke, defeating incumbent Bruce Sinclair in the 1994 municipal election. After a garbage strike in 1995, Holyday and Etobicoke council tendered the garbage collection contract, and inviting CUPE and private operations to bid. Holyday noted that "[CUPE's] price was nowhere near what the private sector offered us", and noted that the contractor did the job with 35 employees as opposed to the previous 71. The move saved Etobicoke $1 million annual at the time, with city officials estimating it at $2 million in 2009, plus private contractors had to post a performance bond and commit to a wage rate for the duration of a five-year contract, which protected the city from a strike. In 1996, Etobicoke also bought out its employees' accumulated sick plan, with new employees not eligible for sick day accumulation.