‘A high degree of collegiality’

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THE DISSENTER Stephen Holyday

Ward 2 Etobicoke Centre First elected 2014

Stephen Holyday doesn’t mind being on the losing side of a vote. In fact, he seems to relish it.

How else to explain his council record, in which he’s been the lone dissenting voice on dozens of measures that otherwise won unanimous support?

He has been the only councillor to vote against: imposing a tax on foreign home buyers, expanding the bike lane network, declaring homelessness a city emergency, asking the province for greater revenueraising powers and road closures for a triathlon.

And that was just this term. He said his propensity for voting in the negative “isn’t a deliberate or defiant stance.” Instead, he sees his role as combating the “groupthink” of a council that has strayed from what he believes is its core mandate of providing basic services, and is instead focused on “the redistribution of income” through policies the city can’t afford, like subsidized housing.

“I feel strongly that it’s my responsibility to ask tough questions, and to challenge the status quo,” he said in an interview.

Holyday, who is the son of former city councillor and Etobicoke mayor Doug Holyday, is under no illusion his objection will flip the outcome of a decision. But he regularly requests a recorded vote to ensure his opposition is registered, believing it’s important to “highlight” when council does something imprudent.

‘‘ I feel strongly that it’s my responsibility to ask tough questions, and to challenge the status quo.

STEPHEN HOLYDAY WARD 2 ETOBICOKE CENTRE

Under Tory, Holyday sometimes voted against key policies of the mayor’s, like exploring a parking tax. But he has diverged with Chow on big issues more often than any other councillor, backing her less than 18 per cent of the time, according to an analysis by the Star’s Matt Elliott. By comparison, Holyday voted with Tory on major issues about 58 per cent of the time in his last full term in office.

Policies of Chow’s he’s voted against include her signature plans designed to address Toronto’s crushing housing crisis, like tripling the vacant home tax and setting a target of 65,000 rent-controlled units.

Holyday said he hasn’t changed his approach under Chow, but since the election of a slate of new progressive councillors in the fall of 2022 and the new mayor taking office last July, there are fewer voices challenging what he sees as government waste and overreach.

“So I think that allows (my voice) to be amplified,” he said.

While Holyday is often an outlier in the council chamber, he believes he has the support of the “silent majority” of people outside city hall who don’t approve of how local government is run. He’s extremely popular in his ward, which is older and wealthier than the city as a whole, and won re-election in 2022 with a whopping 72 per cent of the vote.

Despite opposing many of their ideas, Holyday has cordial relationships with his colleagues, who describe the 48-year-old as informed and polite.

He’s even on good enough terms with Chow that she appointed him head of the newly created committee responsible for improving city service delivery.

Councillors say their working relationship with Holyday is limited by his rigid voting strategy, however. There’s no point in approaching him to ask for his support on an issue, because if he’s already made up his mind he’s unlikely to compromise.

Some also believe he can be hypocritical. He routinely votes against councillors’ requests for local improvements like new stop signs or traffic signals in their wards, because he says they’re costly and politically motivated. Yet he fought to keep the mechanical leaf collection service that his residents benefitted from but wasn’t offered elsewhere in the city. The city scrapped it in 2023.

There’s always a logic to the way he votes, Holyday insisted. “If you couldn’t detect a principle or a consistent approach, then that would be really worrisome.”

What to watch The three-term conservative has always been a lone wolf, but his strategy of voting against measures backed by the rest of council has become more pronounced under Chow. Unless he starts co-operating with likeminded members, his protest votes will be more symbolic than effective.