An old boy net­work or soci­ety can refer to social and busi­ness asso­ci­a­tions among for­mer pupils of top male-only pub­lic schools (inde­pen­dent sec­ondary schools)…and indi­rectly to preser­va­tion of social elites over time with­out regard to merit.

—Wikipedia

My high-school, Upper Canada College, is often touted as one of the best schools to attend in Canada. Someone once said that it pro­vides Canada with a dis­pro­por­tion­ate num­ber of lead­ers, of whom include a Governor General, five Lieutenant-Governors, 24 Rhodes Scholars, and nine Olympic medallists.

The fac­ulty was excep­tional. A pas­sion­ate, charis­matic group, some of them for­mer pro­fes­sors, notable busi­ness­men, intel­lec­tu­als. The facil­i­ties were top notch; foot­ball fields, base­ball dia­monds, ten­nis courts, indoor/outdoor pools, squash courts. Even the bands and the­atre groups had access to exotic instru­ments and props. I remem­ber for a pro­duc­tion of Hamlet they hired a fight chore­o­g­ra­pher to lend his exper­tise in orches­trat­ing the final fight scene.

School isn’t just about the edu­ca­tion though. It’s as much about the expe­ri­ence. The class­mates. The con­nec­tions. The Old Boy net­work.

When I first started at the prep at age seven, I was cycling along a bridge with another lit­tle seven year old UCC chap. He said to me, ‘My mother is so happy that we are friends because you are going to be able to do so much for me in later life.’ I remem­ber think­ing, ‘I won­der what it is that I am going to be able to do for this chap?’ Then I grew up and real­ized, ‘So that’s the way it is. That is what peo­ple expect.’

—Lord David Thomson (1964–1967, 1970–1975), Chairman of Thomson cor­po­ra­tion, Canada’s wealth­i­est man, sixth wealth­i­est in the world

The influ­ence of the elite legacy of the Old Boys is far-reaching. Compounding this is the age of the school, and per­haps a degree of nepo­tism. A related male at the school sig­nif­i­cantly increased the chances of get­ting in.

Like his grand­fa­ther, John was in McHugh’s house. If had a brother or a son, they would belong to Jackson’s.

Years later, I insisted that my sons, Hugh and Stafford, go to UCC sim­ply because I knew from my own expe­ri­ence that once a boy had gone to Upper Canada, he would never again be in awe of great fam­ily names, money, power or social stand­ing. He would know that although a good pri­vate school like UCC can pro­duce the best, it can also pro­duce the worst.

—Conn Smythe (1908–1910), founder, Maple Leaf Gardens

It was only when James Fitzgerald, an Old Boy him­self, pub­lished his best-selling book Old Boys: The Powerful Legacy of Upper Canada College in 1994 (from where these quotes are taken) that the blem­ishes of UCC came to light.

Beneath the veneer of of navy blue blaz­ers and pol­ished shoes were issues like any other school. There were drugs (though much higher-classed because of bet­ter fund­ing). There were sadis­tic head­mas­ters who looked for an excuse to cane their pupils. There were teach­ers who molested — or seduced — their students.

I learned to be a sex­ual masochist at Upper Canada. I’m not kid­ding. Whenever the house­mas­ter caught me mas­tur­bat­ing, his way of deal­ing with it was to cane me. Caning is a rot­ten method of teach­ing any­thing. What it taught me, of course, was the erotic con­nec­tions of can­ing. They are still with me to this day.

—John Gartshore (1935–1943), musician

A cou­ple months ago, I received a copy of Old Times, the semi-annual pub­li­ca­tion for alumni. In a sec­tion called “Class Notes”, they bring oth­ers up to speed on their class­mates. In the last issue, for exam­ple, they men­tion that Michael Ignatieff, class of ’65, had just joined the race for the lead­er­ship of the Liberal Party of Canada.

There are updates start­ing from the grad­u­ates of 1941, includ­ing my grad­u­at­ing class, the class of ’99. Out of curios­ity, I looked back on my year­book, The College Times, Canada’s old­est stu­dent pub­li­ca­tion. I had to won­der just how much the pres­tige of the school had helped them. To com­pare my idea of where I believed my fel­low class­mates would be, with what they’re doing now.

The mem­o­ries I had didn’t always match up with their cur­rent achievements.

The Old Boys of ’99 Series

1. Introduction
2. Another Perspective
3. Seeto and Bunston
4. Mungovan and King
5. Providing Ignorance as Bliss
6. My Perspective