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I apologize, that sounded condescending.
I read the entire judgement and basically it boils down to there being two different processes. The proper way to challenge a heritage designation is by making an appeal of the designation or the refusal of a demolition permit under the Heritage Act. It entails an entirely different process / legal test for heritage protection than the Planning Act, so it can’t just be skipped by the OLT. Likely for tactical reasons, the developer chose not to go this route, which may end up being a fatal choice. TBD. Also, the OLT was criticized for essentially disregarding Council’s decision to designate.
Justice Perell has been a judge for a long time. He’s been wrong before, like all judges, but he explains himself very clearly in the decision as to why you must challenge a heritage designation under the Heritage Act. Maybe the decision will be overturned, but the reasoning is not a legal fiction and I’m not sure why you think he’d have that animus.
As for the City’s tactics, due to resource issues, designation (for better or worse) often comes after a planning application is received. In this case, the property had already been listed as part of a Heritage Conservation District in 2016, and the listing has been under appeal by the property owner for several years. As such, that the City was going to fight on heritage issues was no surprise to anybody.