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Last summer, it was the conversion of the very 'Mad Men' 1950s Imperial Oil building at St. Clair Avenue West and Avenue Road into condominiums; this summer, it's the Brutalist, late-1960s Four Seasons building at the corner of Yorkville Avenue and Avenue Road: is David Feldman on a one-man mission to save Toronto's stock of mid-century modernism?

Perhaps not, but it's worth noting that in 2007 Menkes Development Ltd. filed an application to demolish the building and replace it with two tall towers. One, at more than 50 storeys, would have popped up like a pimple on the Queen's Park roofline when viewed from College Street; not surprisingly, this caused an outcry in the heritage community and a long discussion on the protection of view-corridors.

"I didn't like the idea of tearing it down," says Mr. Feldman, adding that Yorkvillers will now enjoy "two years less disruption." Calling the building an "iconic structure," his company, Camrost-Felcorp, firmed up the deal to purchase it earlier this year, and, if all goes according to plan, new owners will call the former hotel home sometime in 2014.

In fact, Mr. Feldman is so convinced this building is an icon – the editors of the 2007 book Concrete Toronto affectionately call it "a mountain" – he's hired the architecture firm originally responsible for its creation in 1969, WZMH Architects, to oversee its 21st-century transformation. "When David called, it was an amazing opportunity for us to be involved in the project," says Brain Andrew, a 30-year veteran at WZMH and one of the firm's principals. "We've been involved in the area in a certain sense for 40 years: we did Hazelton Lanes, our offices used to be at 99 Yorkville … and we've seen a lot of the transformation and coming of age of Yorkville."

This building, it could be argued, was the most visible face of that cultural shift from hippie hangout to tony shopping destination and film festival hotspot when it opened for business in 1971, but it didn't start life as a Four Seasons.

Built originally as a Hyatt Regency, Four Seasons founder Isadore Sharp didn't acquire the property until 1978: "To be able to have a hotel [in Yorkville]was important to us, so we were in the process at the same time of looking for a site to build a hotel and this one came to our attention," he says. And, despite the emergence of his company into a global brand by the late-1970s, Mr. Sharp remembers hotel co-owners Ken Field and Dick Shiff (of Bramalea Ltd) had to convince the big boss, Jay Pritzker – creator of the Pritzker Architecture Prize – to let the Four Seasons rebrand it.

"Once we bought it we made major changes to try and get it as close to a Four Seasons as we could," remembers Mr. Sharp. One major alteration was to increase room size, so the count went from 620 down to 338; his wife, Rosalie, handled the interior redesign of the rooms in addition to the ballroom.

Of course, the room count will change yet again to a number somewhere halfway between those two figures after it's been determined how many two-bedroom units will be ordered over the smaller one-bedrooms and pieds-à-terre, notes David Feldman. What is certain is that prices will start in the pocketbook-friendly mid-$300,000s, like at Imperial Plaza, "which is incredible for Yorkville," he offers.

Retail at the building's base will change also, but Mr. Feldman hints it will be welcome, as he's already been "approached by a number of world-class retail institutions" and "restaurants from New York." Former Art Gallery of Ontario curator David Moos is working on the addition of a sculpture park for the Avenue Road side of the base.

So, with that much change, should those who enjoy the building's muscular Brutalist lines be concerned? While early renderings by WZMH show much larger retail openings, the distinctive flared columns will remain visible in all their groovy bell-bottomed glory. And despite much of the second floor's chunky 'broken-rib' concrete being covered by an "overlay" of large enameled glass screens, it will most likely be possible to glimpse it underneath, since the screens will feature a mixture of opaque and transparent sections with creative backlighting. This will give these original elements the look of being in "a vitrine" explains WZMH's Mr. Andrew: "The trick is getting the balance right so you don't lose the image and the presence of the building." To that end, the tower itself will remain relatively untouched, with only the corner balconies being glassed-in to increase floor space inside the units.

While many consider Brutalism rather, well, brutal as compared to the much sleeker Mad Men style of Modernism, Isadore Sharp calls his former hotel "a very handsome building" and all indicators suggest that Mr. Feldman, Mr. Andrew and the Design Agency's Matt Davis and Anwar Mekhayech (hired to handle the interior revamp) are of a similar mindset.

This is good news for those of us who appreciate Yorkville's recent architectural past. The only thing that's off the mark, in my humble opinion, is the decision to name the suites "Manhattan," "Paris," "Milan," "London" and the like. While obviously meant to indicate the sorts of places from which potential buyers might hail, I'd argue that naming suites after the area's legendary 1960s coffee houses – the Riverboat, the Penny Farthing, the Purple Onion, Chez Monique and the Mynah Bird to name but a few – would honour the neighbourhood's cultural past as well.

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