On warm evenings, urban designer Ken Greenberg likes to serve dinner on his balcony and watch Toronto’s skyline light up in the dusk.

“It actually is magical,” says the city’s former urban design and architecture chief, whose perch near King and Bathurst Sts. puts him in the front row for the nightly performance.

That impressive show may be set to go full-blown Broadway on Greenberg, with a host of towering new players — in various stages of planning and approval — poised to hit this city’s downtown stage over the next five years.

Predicting skyscraper development is a mug’s game, says Greenberg, with economic and engineering contingencies almost exclusively driving what actually gets built and how.

But as it stands, 10 projects boasting towers of 240 to 300-plus metres are slated to join Toronto’s skyscraper cast by around 2020 in what’s being called the “Manhattanization” of the city’s skyline.

These include a two-tower project by Toronto-born architect Frank Gehry and theatre impresario David Mirvish in the Entertainment District. At 92 floors and 305 metres, the larger of these jagged King St. W. skyscrapers would become the city’s tallest habitable building.

Up at Bloor and Yonge Sts., a single tower entry — christened The One — would stand at 80 storeys and 304 metres. Now before the Ontario Municipal Board, this 1 Bloor St. W. project could be the first of the new skyscraper crop to see shovels in the ground.

Both the Bloor St. and Mirvish-Gehry projects would sprout buildings surpassing First Canadian Place at Bay and King — which, at 298 metres, has held the city’s height crown for 41 years.

So too would a 95-storey structure by developer Pinnacle International that will rise 303 metres and form the spine of a five-building project set to transform the foot of Yonge St.

This trio of projects would also include Toronto’s first entrants into the rarefied realms of “supertall” buildings — a designation the respected Council on Tall Buildings and Urban Habitat confers on skyscrapers of 300 metres or more. (At 553.3 metres, the CN Tower will still dwarf all foreseeable comers, but it is listed under a separate “tower” category by the Chicago-based council.)

These and other planned skyscrapers would also add an increasingly distinctive north-south axis to the city’s downtown cluster, which itself is rapidly expanding eastward and westward along the lakeshore.

This dual spread will give the city’s skyline an “upside down T” configuration, says Gregg Lintern, director of community planning for Toronto and East York.

Many experts say it will also alter, in more intangible ways, the perceptions and images that will be formed of this city, at home and abroad.

Symbols of human ambition

Skyscrapers, in important ways, are the modern equivalent of medieval cathedrals, says University of Toronto philosopher Mark Kingwell.

“They have the same kind of effect on those of us who love them,” Kingwell says. “They are a human-made thing that has this kind of soaring ability to rise above and transcend everyday life.”

And like their medieval counterparts, which towered over European towns for centuries, they can broadcast a city’s pride and aspiration, Kingwell says.

The skyscrapers “bespeak a certain kind of civic and human ambition that no other building form captures quite so well,” he says. “So when I think about the cities around the world that I love, the first thing I think about usually is the skyline.”

And Kingwell, who wrote the 2007 book Nearest Thing to Heaven: The Empire State Building and American Dreams, says it’s common for visitors to judge a city by its skyline covering. And bigger is often seen as better.

“That’s traditionally been one of the associations with tall buildings,” he says, recalling the awe expressed by immigrants and visitors arriving by sea to early-20th-century New York.

“They saw this island of Manhattan as just this kind of unbelievable mountainscape of built structure. The building and the aspiration and the sense of progress was so much alive.”

Greenberg adds: “The skyline of a city is a kind of signifier. People read into it something about what they think the place is like and what they think the experience of being there will be.”

And in many cases these perceptions are proven true, Greenberg says.

In his native New York — again the prime example — the promise of Manhattan’s exhilarating skyline has been borne out fully in the furious pace of life at its base.

“There was this exciting, vibrant life on the sidewalk,” he says. “There was great entertainment, extraordinary shopping, liveliness. It was a draw for young people from all over the world.”

Likewise in cities like Chicago, Tokyo and Hong Kong — whose big-league skylines Toronto is poised to join — life on the ground can match the flamboyance of their collective towers.

But skylines can tell tall tales, Greenberg says. He says impressive skylines in many cities belie bleak realities down on the pavement.

“Dubai is a place that has one giant building after another … but no one could accuse it of being an exciting or wonderful place to be,” he says. “It’s a bunch of highways down below.”

The expansive downtown skylines of Atlanta, Calgary and Los Angeles cast shadows over fairly listless streetscapes, Kingwell adds. Ideally, “the tower grows out of the energy from the ground beneath it,” he says.

So will Toronto’s bulked-up skyline bear true or false witness to its street-level realities?

“The jury is out,” Greenberg says.

Toronto’s vibrant downtown holds some advantages over many vertically ambitious cities, he notes. For one, this city’s centre held in the last half of the 20th century, never experiencing the “white flight” of many U.S. metropolises, sending more affluent residents to the suburbs while denuding and impoverishing their cores.

For another, says Greenberg, a fortunate inertia among successive municipal governments here in the 1950s and ’60s saved Toronto from the myopic transportation choices that have stilted downtown potential in many North American centres.

“We failed to do the stupid things that other cities did,” he says. “We were slow in ripping up the streetcar tracks, we were slow in building the expressways, so when we stopped it wasn’t too late.”

Perhaps most importantly, however, a significant majority of the planned skyscrapers in downtown Toronto will include massive numbers of condominium units, which would bring in hundreds of thousands of residents to enliven what was long considered a sleepy business district.

But Toronto’s onrushing vertical climb has already produced mixed results, Greenberg says.

Highs and lows in Toronto

The CityPlace neighbourhood, which is expanding Toronto’s skyline westward across the railway lands, has integrated its condo towers with an increasingly spirited street scene.

“CityPlace is actually becoming a pretty interesting neighbourhood,” Greenberg says. “It has the Canoe Landing Park, it’s getting two new schools and a community centre. It’s getting some restaurants and cafés, and Bremner Blvd. is becoming more interesting.”

Meanwhile, the massive buildup of increasingly tall condos around the Humber’s mouth has, so far, been unaccompanied by a similar ground-level liveliness.

“There’s a nice park — the Humber Bay Shores Park — beside that area,” Greenberg says. “But within the fabric of those really tall buildings … it’s kind of bleak. There’s no there there.”

Likewise, the area south of Union Station is being crammed with some of the city’s tallest condos, Greenberg says. But he calls street level a “highway environment.”

Toronto planners’ priority, then, is to ensure the ground game keeps pace with the cranes as they rapidly hoist the city upwards, Greenberg says. This not only means upgrading “hard” services like hydro, sewers and transportation, but also providing “soft” infrastructure like parks, schools, daycare, community centres and shopping.

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Greenberg says as well that new buildings should include some “serious public space” in their footprint plans.

Even along Yonge St., where buildings line the sidewalks cheek by jowl from Front St. up past Bloor, there’s room for open plazas, Greenberg says. By using the backing laneways, existing pocket parks and the land behind new buildings, projects can eke out public spaces while maintaining much of the street’s ramshackle essence.

“There are endless opportunities all the way along.”

Lintern of the city planning department is on board with these ideas and is helping direct the city’s emerging TOcore strategy to ensure ground support for the vertical climb.

He says the city has had plans to increase residential density downtown since 1976, when First Canadian Place and the CN Tower were the tallest buildings and about 100,000 people lived in the core. In 2011 that population had grown to 200,000 and it could hit 475,000 by 2041. That rapid residential influx, Lintern says, has been positive, but is also a strain.

“We’ve had so much success (that) our infrastructure, in some areas, is beginning to show signs of pressure and deficit.”

For example, Lintern points to the narrowness of the city’s downtown sidewalks, which were laid out by British military surveyors in the 1800s.

“We’ve got these 20-metre (street widths) that the British soldiers laid out (using) the width of whatever chain they had.”

Lintern says the city is working hard to create wider downtown sidewalks where possible, while many still dream of creating a pedestrian mall along lengths of Yonge St.

In the second year of an expected three-year preparation phase, TOcore will update the 1976 plan and concentrate on seven areas. These include guidelines on locating buildings and ensuring there is enough water, transportation, hydro, parks and public space, schools, libraries and commercial infrastructure to support them.

Developer’s-eye view

Planning success, the city’s Lintern admits, will rest in part on the willingness of developers to share in the cost and provision of needed facilities and upgrades.

Mike Collins-Williams, director of policy with the Ontario Home Builders Association, says there’s really little tension between the city’s need for ground-level amenities and the economic imperative for skyscraper builders to provide them.

“We’re creating communities; we’re not creating towers,” Collins-Williams says. “So absolutely it’s critical (for us) to get the ground right.

“From the developer’s perspective, these are very large, very expensive projects and to make them work and to make them appealing for people to purchase … or rent, you’ve got to provide a lot of different amenities.”

Collins-Williams says virtually any large project coming up will have a mixed-use configuration, with residential towers on top and shopping, office or recreational facilities in a podium base. For example, the Pinnacle project at the foot of Yonge will include a large community centre at street level, he says. The stores or businesses that will sit below the towers are crucial to provide rents to offset building costs.

“Any developer will want to put … their best foot forward so that their project at this scale appears to be a step above the others in the area.”

However this groundwork unfolds, Lintern says new downtown dwellers are already adopting one of the city’s hallmark features — with the core becoming “a downtown of neighbourhoods.”

Where once the downtown was seen as a separate, monolithic entity, flanked by Cabbagetown, Kensington or the Annex, newcomers are self-identifying as residents of St. Lawrence, Church-Wellesley Village or the Waterfront, he says.

Ultimately, though, the success of a skyline also depends on its vertical architecture, Greenberg says. And the esthetic merits of Toronto’s cityscape will depend on the design of its “signature pieces” as well as the spreading ensemble.

Back to his New York example, Greenberg, who is also an architect, says the appeal of Manhattan’s skyline is based in large part on the iconic stature of recognizable structures like the Empire State and Chrysler buildings. But developers’ splashy renderings of Toronto’s coming skyscrapers have left him underwhelmed.

“I’m still waiting for something that I would say: ‘It’s a real architectural breakthrough that has done something different or extraordinary.’”

Indeed, Kingwell says the CN Tower may be the sole structure guaranteed an iconic presence in the years ahead.

Other landmarks like Mies van der Rohe’s Toronto Dominion Centre could be all but obliterated on the skyline by taller but lesser pieces of architecture, he says.

“I would just like to see maybe one or two more signature or standout buildings in a lot of these things that are going up.”

He says the proposed Gehry project could claim “monumental” status. But even these King St. W. towers, Greenberg says, could lose some of their iconoclastic appeal to the realities of cost and engineering considerations in their final iterations.

But Collins-Williams is confident that economics will drive developers to produce attractive towers, especially for higher-end condo projects.

He says the recruitment of expensive, superstar architects like Gehry and Britain’s Norman Foster — who drew up 1 Bloor St. W. — show high-quality design is a decided plus for successful condo sales.

“I think it’s naive to think there’s never going to be friction in the planning process,” Collins-Williams says.

“But there are sometimes interests that can align well,” he says, and create a better city.

How all these forces interact in Toronto will answer the question: is higher better?

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