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Peter Clewes, Toronto’s most acclaimed condo architect, avoids his own work sometimes.

He’ll be driving downtown, on his way to the office at 5 a.m. say, and he’ll make an extra turn. He’ll loop around to skip certain buildings. Or, if he’s walking, he’ll keep his head down and not look up at the structures he would rather not remember.

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“I like maybe 20% of what we do,” Mr. Clewes said. Which means that, after more than 30 years in the industry, there’s a lot he doesn’t like.

There are buildings that didn’t work out, visions sacrificed to budgets or bureaucracy. And each of those eats at him, in its own, painful way.

“I think about it a lot,” he said. “It really, really upsets me.”

His career is as a kind of contradiction. For decades he has sought to bring art to a form — the condominium—most deride as artless. And for all his fretting, he has, in the eyes of most critics, succeeded many times.

But in the midst of Toronto’s unprecedented condo boom, when he could be forgiven for taking a kind of extended professional victory lap, he is instead beset by worries, about his own work, yes, but also about condos more generally, about how they’re being built here and why, and what it will mean for the city if things don’t change soon.

“We don’t take the public realm seriously,” he said, on a recent weekday morning at his office in downtown Toronto.