Last Holyday: the highs and lows of Doug Holyday’s career in city politics

Last Holyday: the highs and lows of Doug Holyday’s career in city politics

(Image: Christopher Drost)

City hall will be a different place without Doug Holyday. After 28 years in municipal politics, the deputy mayor joins the Progressive Conservative caucus at Queen’s Park later this month, having beat fellow councillor Peter Milczyn in an Etobicoke-Lakeshore provincial byelection. Of course, none of Holyday’s former colleagues already angling for the vacant seat mix crabby exasperation, fiscal conservatism, courteousness and a deep love of pocket squares like the former Etobicoke mayor. Below, a few of the best and worst moments from Holyday’s time at city hall.

• Some of his zingers were witty…
Though the usually courteous councillor mostly stayed clear of the childish antics so common in Toronto politics, he did deliver some memorable bon mots. Our favourites: christening union president Mark Ferguson “Dr. No” for his unwillingness to negotiate, and his irritated plea to voters after losing an important council vote: “Don’t send us any more activists. Don’t send us any more unionists. Don’t send us any more cyclists. Send us some people down here with good common sense.”

• …others were just dumb
Holyday’s famous comments about the condo-dwelling youngster “Little Jenny” playing in traffic revealed a prejudice against downtowners and made the lawn-loving suburbanite seem out of touch.

• He fought the gravy train long before Rob Ford came along…
Holyday’s reputation for being a miser dates back to his time as the mayor of Etobicoke, where he once went after a city manager who racked up thousands of dollars of charges at strip clubs, restaurants and bars on his city-issued credit cardLater, the famously frugal Toronto councillor revealed a deep obsession with his colleagues’ offices expenses, railing against everything from “pricey meals at fancy restaurants” to donations to local sports teams.

• …but some of his money-saving plans backfired 
Holyday personally sued the city to challenge a 2008 decision to cover two councillors’ campaign-related legal fees, saying he felt strongly enough about the principle to pay for the suit himself. After he won, however, the costs were far more than he’d expected and he was forced to ask the city to help pay for suit. Oops.

• He did his best to help Rob Ford…
The veteran politician played a central role in two of Ford’s major victories: outsourcing garbage collection and signing contracts with Toronto’s public sector unions. He made a public push for the intractable Ford camp to embrace the art of give-and-take, telling reporters, “You have to work with some of the people on council to get things passed. That’s the way the system is intended to work.”

• …Ford didn’t always listen
Despite many attempts to steer the freewheeling mayor in the right direction, Holyday has largely failed to exert a steadying influence over Ford, who has limped from political loss to scandal for much of his mayoralty.

• He brought style to city hall
The 70-year-old is never seen in anything but a sharp suit with a tie and a perfectly folded pocket square. He may not be city hall’s most swooned-over gent, but he’s certainly its most dapper.