Two mammoth towers will soon completely redefine the city's skyline, part of a major redevelopment transforming the Toronto Star lands at the foot of Yonge Street.

The sprawling Pinnacle One Yonge development has already added one new tower to the skyline, but it is the complex's second and third phases that will dramatically alter postcard views of the city with what could include Canada's tallest building.

Already approved at soaring heights of 80 and 95 storeys, a height increase was proposed for the Pinnacle One Yonge complex's two tallest phases in late 2022 that, if approved, would increase their heights by 12 and ten storeys, respectively, to staggering heights of 306 and 345 metres.

Pinnacle One Yonge's SkyTower (phase 3) rising against the first phase condo tower known as The Prestige. Photo by Fareen Karim.

For a reference point, the city's current tallest building and most prominent skyline point after the CN Tower, First Canadian Place, stands at a height of 298 metres. If completed today, these two condo buildings would both overtake that colossal bank tower as the city and country's tallest buildings in the #1 and #2 positions.

However, that ranking may not necessarily be the case when both are completed. We'll put a pin in that for now, though, and focus on where the Pinnacle project is currently at.

The tallest tower at this Pinnacle One Yonge site, dubbed SkyTower for marketing purposes, is already well under construction and will soon begin to pierce the skyline.

Its enormous podium is now fully formed, and work has begun on the tower floors above. With a much smaller footprint for crews to shape, these levels should rise significantly quicker than the progress seen thus far.

It may not look imposing yet, but this construction site could soon host the tallest building in all of Canada. Photo by Fareen Karim.

Now, back to that uncertainty.

Throughout SkyTower's planning and even into its construction, its developer, Pinnacle International, has been duking it out with rival Mizrahi Developments' The One to lay claim to the title of Canada's tallest building.

SkyTower's smaller tower floorplates are beginning to appear above its podium. Photo by Fareen Karim.

Both developers applied for height increases in the last few years, and Mizrahi's application was recently granted an increase from the approved 85 up to 91 storeys, a compromise from a late 2020 bid seeking approval to build up to 94 storeys.

The One's approved increase — now permitted to rise just over 328 metres — while generous enough to take the title of Canada's tallest from the current reigning champ, will likely result in a short-lived crown for the project at Yonge and Bloor.

SkyTower beginning its ascent above Yonge and Harbour Streets. Photo by Fareen Karim.

The One is much further along in its construction than SkyTower, and, though it will undoubtedly be able to boast the title of the country's tallest building (not structure, as the CN Tower is classified) for a brief period, Pinnacle seems on the cusp of gaining approval for its height increase, and with it, this illustrious but ultimately meaningless title.

Canada's tallest building will soon tower over Toronto's Yonge and Bloor corner https://t.co/Ab7tk8cfwo #Toronto #RealEstate

— blogTO (@blogTO) April 30, 2023

This would mean yet another new tallest building for Toronto within a short time of The One stealing the crown from First Canadian Place, a title that has gone more or less unchallenged since 1975.

The potential approval of Pinnacle's proposed height increase for the SkyTower (and its shorter sibling by association) would prove the final salvo in Toronto's current race to build a new tallest tower, ending the competition with One Yonge reigning top dog.

Harbour Street will eventually be extended eastbound between the new towers and the current Toronto Star building in the empty space visible at the lower right. Photo by Fareen Karim.

While The One's current approved height is indeed taller than the approved SkyTower height of just over 312 metres, Pinnacle's proposed height increase of over 30 metres would give its developer the last laugh.

For now, though, that's still an "if," giving Mizrahi Developments hope for their claim to the title.

If you want to look at this in football terms, Mizrahi is up by a point with a minute on the clock, but Pinnacle has possession, first down, and the ball on the one-yard line.

SkyTower's podium levels have taken approximately one year to reach this point following construction of its massive underground garage. Photo by Fareen Karim.

It may not prove as dramatic in terms of architectural legacy, but the race playing out at these two points a few kilometres apart on Yonge Street is not unlike the battle for the skies seen in Depression-era New York City.

That historic war for skyline domination culminated in a similar back-and-forth of height increases and spire additions where the Empire State Building ultimately beat out the Chrysler Building for the title of the world's tallest building — a title it would retain from its completion in 1931 to the construction of the original World Trade Centre's twin towers in 1971.