One of Toronto council's staunchest conservatives, he is noted for his fiscal conservatism and tendency to oppose public spending measures. 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. In addition to his fiscal conservatism, Holyday has also supported conservative policies in other fields. For example, he opposed banning gun clubs in Toronto, as well as a decision by council to ban the Toronto Sportsmen’s Show from the CNE (council later reversed its decision). He has proposed removing the homeless from Nathan Phillips Square, and was the only member of council not to vote for a resolution describing homelessness as a national disaster. 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. Holyday also supported reducing the number of councillors, and voted against childcare subsidies. In 2012, Holyday proposed that casino lobbyists be banned from city hall, stating "I think the fairest way to do it is to take that part out of the equation".