It is also the oldest Catholic high school in upper Canada, part of a religious tradition that is nothing if not patriarchal. So it seems odd that women now run the place - odder still that out of the five high schools in my church-led authority, two have entirely female senior management teams.
It is part of a broader trend. Internationally, teaching is becoming feminised. Here in Ontario, for example, 70 per cent of new entrants to the profession are women. And judging by "concerned parent" callers on radio phone-in shows, that's not a good thing. Children, they say, need both male and female role models. They want more blokes in the classroom, and quickly.
Pundits point to a number of possible reasons for the dearth of men.
Perhaps they're concerned about false accusations of sexual abuse. Perhaps they're not happy with the pay (although teachers do much better than in England).
To me, though, it seems that the feminisation of teaching points to a more fundamental problem. When women dominate a profession, it is because that profession is not valued. There are many precedents for this. In the early 18th century, novel-writing was poorly paid and infra dig. Two-thirds of published novelists were women. But by the 1840s, when the social status of fiction had risen, 80 per cent of it was written by men. Women only began staffing telephone switchboards when it turned out that the young boys originally hired for the task didn't have the attention span.
Look, too, at divisions within professions. Women are more likely to be family doctors than neurosurgeons. And guess which of those jobs, in medical circles, is by far the least prestigious?
Teaching, of course, has its own history of gender division. While men established and ran prestigious boys' schools such as Eton, women taught the unimportant poor. Even now, in a female-dominated profession, men are likely to be found where there's less overt nurturing to do. They're also more likely to be perceived as clever, and their working conditions are better. You'll find them in high schools rather than primaries.
Despite attempts to make teaching a more attractive career, governments in both England and Ontario have made matters worse. Recent initiatives, be they curriculum changes or inspection regimes, have been overwhelmingly punitive. Consequently, teachers feel talked down to, second-class and less autonomous. Couple this with the public feedback which manifests itself at times of debate and change ("Cut down their holidays!" "They knock off at 3.30pm!" "My son can't read!") and it's hardly a recipe for professional pride. Historically, women are used to such humiliations. But men are not.
The general atmosphere of condescension has worsened in more subtle ways.
For example, professional development courses often pander to the worst stereotypes of touchy-feely femininity. Recently, I was made to stand in a circle with colleagues. We held a long ribbon in the air, and when one of us let go, it fell down. This was to demonstrate the importance of teamwork.
Meanwhile, friends who teach in Manchester tell me they now attend twilight training sessions for which they are rewarded with Mamp;S vouchers. Why has teaching become a Tupperware party?
It is therefore no surprise that, even in macho schools like mine, women are now in charge. If men want power - and they always do, whether it's schoolboys dominating lessons or presidents dominating the world - they are hardly going to move into a role that is constantly questioned, manipulated, patronised, and therefore degraded. Women will continue to fill the gaps, as they always have.
So I pine for more men in my school. Not because they are better at the job, but because their presence will mean teaching is recovering. It is appalling to acknowledge that a female-dominated profession is a profession in crisis. Yet when 70 per cent of new teachers are women, it is a crisis that cannot be ignored.
Nicholas Woolley teaches in Toronto, Canada