For some reason my mind keeps wanting to insert something like the
Gardiner Museum there.
I adore contemporary architecture, but this seems to be a generic solution — somewhat aloof and context-obtuse.
The intersection of James & Main (St. Paul's, 1854; Hamilton Club, 1873; Sun Life Building, 1905; Landed Bank, 1908; Bank of Montreal Building, 1928; Pigott Building, 1928) has endured for generations against the odds.
Would be nice to see some forward-thinking infill that won't look dated in half that time.
As previously noted, the architectural design challenge will be to create an infill structure that aesthetically connects Stanley Roscoe's tower at 25 Main with John M. Lyle's 1 Main West/52 James South.