In 1974, Toronto was home to roughly two million people. The skyline was growing rapidly — including the under-construction CN Tower — and the city was already filled with iconic buildings, from the old Maple Leaf Gardens to the recently-opened new city hall.
One thing the city didn't have? A modern flag.
At the time, Toronto was just using its coat of arms on a blue and white backdrop, much to the chagrin of previous mayor William Dennison, who didn't think it was "really a flag at all."
"It wasn't particularly popular," says historian Chris Bateman, manager of plaques and public education for Heritage Toronto.
"It flew a handful of times, but never got a lot of love from the public."
And so, the city created an official Flag Design Committee, with aldermen — the old term for what are now called councillors — Paul B. Pickett, Q.C. and Reid Scott, Q.C. as co-chairs and Edward Negridge, Colin Vaughan and Anne Johnston as members.
The committee wound up hosting a public competition to find a fresh option. All residents of Metropolitan Toronto were welcome to submit one design each with an explanation for what inspired it, with a $500 Canada Savings Bond as the prize.
Around 700 people sent in entries — including Rene De Santis, a 21-year-old graphic design student at George Brown College.
Inspired by the curves of city hall from the viewpoint of Nathan Philips Square, he developed what wound up being the winning concept: A white T-shaped design, mimicking that striking concrete building, against a royal blue background with a bright red maple leaf.
"The great thing about city hall, it has that kind of motion with the two wings on either side of it — that curve to it — which is just perfect," De Santis recalls. "I could've made it straight, but why straight? The flag is always sort of moving."
CBC Toronto caught up with De Santis recently, close to half a century after his design was crowned victorious in a flag-raising ceremony in late 1974.
The former student went on to jobs in marketing, and did a stint as a court sketch artist, and is now president of Montana Steele Strategic Marketing, a leading Canadian real estate marketing group based in North York.
He traces all his success in the design world back to winning that mid-1970s competition — but says getting Toronto's flag in the public eye since then has been a tricky process.
"I felt a sense of pride," he says. "I felt that I was going to create some sort of legacy."
Instead, the flag was often cast aside or forgotten.
Flag met with 'cheers and whistles'
For the latter half of the 20th century, it was rather the Metropolitan Toronto flag that dominated the scene. Then the first copy of the new flag designed by De Santis was stolen from the flagpole near city hall.
Then, as Toronto's six lower-tier municipalities began the amalgamation process in the late 1990s, officials decided the time had come to find a new option for the "megacity."
Cue another competition — this time with a $3,000 honorarium and strict criteria allowing only three colours in each design and a three-by-six format.
According to city records, council didn't approve a single one of the 161 design submissions, prompting city staff to whip up some ideas, instead.
That's when De Santis stepped back in with a suggestion: Why not just tweak his old, winning design and use that?
After months of "heated debate," city records show Toronto's deputy mayor wound up polling the audience at a November 1999 council meeting on which flag they liked best, between De Santis's design and a recommended option from then-councillor Brad Duguid.
"Councillor Duguid's design received polite applause while the former Toronto flag evoked cheers and whistles from the audience, clearly the favourite," according to the city record.
With that, council officially adopted the De Santis design in a 31-14 vote.
Council voted to explore more uses for Toronto's flag
But two decades later, there's been little uptake on the flag.
"We get tens of thousands of new visitors in this city every year," says De Santis. "Citizens themselves don't really know there's a flag that really exists ... it hasn't been promoted or exposed as a symbol."
However, that could soon change. In January, council voted in favour of a member motion from Coun. James Pasternak, calling for city staff to develop a new strategy for incorporating the flag in city events, communications and marketing, and a report is expected back later this year.
"Torontonians are very proud of their city," says Pasternak, "and there's no harm in strutting it a bit."
The decades-old flag remains a source of civic pride, he explains, even as Toronto residents have gravitated toward other, sometimes more organic, symbols of the city: sports team logos from the Raptors to the Blue Jays, icons and branding of raccoons and the cheeky-but-accurate spelling of "Turrono," the nickname "The 6ix" as coined by the world-famous Drake.
"There's no doubt we're competing with other symbols," Pasternak says, citing even other flags of higher prominence, including the iconic Canadian Maple Leaf and flag of Ontario. "We're like a de facto province," he adds.
De Santis is hopeful his underused design gains more prominence, whether on street signs or official marketing materials.
"There's not a strategy in place to say: 'This is our symbol,'" he laments. "And every brand needs a symbol."
But Bateman, looking through a historical lens, says the flag's low-key status speaks to how Toronto has long operated — as a region still figuring out its own character, and sometimes afraid of showing off too much, even as the city grows.
"People don't really think about the Toronto flag, and in a way, that's a seal of approval," he adds with a laugh.
"If it was dreadful — some kind of design people didn't identify with — it would be more on people's minds."