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OSC investigator John Aiken.Fred Lum/The Globe and Mail

John Aiken, a former stock trader who got his start during the Depression and became a fixture on Bay Street for 70 years, often lamented that computerization had drained the fun out of his beloved stock exchange and kicked many of its strange characters to the curb.

"The laugh has gone out of the business," he told The Globe in an interview in 2004, granted on the occasion of his retirement at the amazing age of 87 from the Ontario Securities Commission's investigations department, where he capped his extraordinarily lengthy career. "People like Bud Scott, who owned the brokerage Scott and Co., throwing his shoe at a trader to get his attention. You pick up any medical journal, and they'll say the laughing is healthy. There's not the personality now by a long shot."

Mr. Aiken died on Oct. 10 at the age of 98, in a long-term care facility in Georgetown, Ont., where had moved in June after his health finally began to fail him around last December. A dapper dresser rarely spotted without a fedora, he was a charter member of the class of characters whose fading he lamented, among the last of a generation of Bay Street veterans with working memories of the Toronto Stock Exchange's freewheeling, whisky-soaked, cigar-smoke-clogged trading floor of the 1930s.

John Herbert Aiken was born on April 18, 1917, to William and Ethel Aiken, the second-youngest of seven children. His father, who had come to Canada as a child from Northern Ireland, worked as a machinist and was a staunch labour unionist, Mr. Aiken's nephew Tom Bainbridge said. The family lived in Toronto's west-end Junction Triangle neighbourhood, on Symington Avenue.

But Mr. Aiken did not get along with his father and left home for good at 15. Riding rail cars – on the top, according to stories he told grandson Jason Juelsberg – he hitched his way to Sudbury, looking for work in a mine.

"He rode on the top of the train with a piece of cardboard in front him to deflect the rocks," Mr. Juelsberg said, adding that his grandfather told him he slept in abandoned cars and rooted through farmers' fields for food.

A year later, in 1933, Mr. Aiken was back in the big city, working at the Standard Stock and Mining Exchange, a rival to the Toronto Stock Exchange that would later merge with it in 1937. Through a school friend's father, he got a job with a brokerage house marking stock prices on chalk boards, a frantic occupation in those pre-electronic days that involved memorizing stock symbols and tracking not just Toronto stocks but prices coming in via ticker tape from the American Stock Exchange and the New York Stock Exchange.

He soon graduated to phone clerk and then to a stock trader when he was just 18. He was counselled by the president of the brokerage to lie about his age in order to get the job, which stock exchange rules deemed had a minimum age of 21: "As I turned to go out the door, he said, 'John, by the way, how old are you?' I said, 'Twenty-one, sir.' He said, 'Good, you remember that when you go before the approval board [of stock exchange governors]."

The frenzied floor of a stock exchange back then was home to hundreds of traders who shouted, jostled, swore, bickered and even came to blows as shares changed hands. And the mining exchange was a Wild West environment, even for its day.

Mr. Aiken said one day some prankster traders tossed water bombs from the elevated visitors gallery onto their fellow traders. The day the mining exchange closed and merged with the Toronto Stock Exchange, a trader (or more than one, in some retellings) pulled out a rifle and began blasting away at the pigeons sitting in the rafters of the exchange's ceiling skylight windows.

With starting pay for his job on the chalkboards at just $7 a week, Mr. Aiken needed some sidelines: He ran a haberdashery out of an office closet, his grandson said, and even worked with a tailor as a partner, measuring Bay Streeters' inseams and bringing him orders for new suits. He also started investing his own money in stocks.

His trading career was interrupted by a stint in the Royal Canadian Air Force during the Second World War. He trained as a tail gunner, although his family said he was not sent overseas.

In 1941, he married Betty Dryden at the Alhambra United Church in Toronto's west end. They had a daughter, Mary Lynne. His wife died in 1980.

After the war, he was back at the exchange and investing his own money on sometimes wildly speculative stocks. Once, he said he lost $4,000 overnight when he only had $3,000 to his name.

In the 1950s, after a market windfall, he decided to buy a farm in Terra Cotta, Ont., northwest of Toronto, where he lived and kept a handful of standardbred horses that he entered in harness races in nearby Elmira, Ont. He said the farm was the best investment he ever made: "When I sold it in 1996, I made over 80 times what I paid for it. I never did remotely close to that in the stock market."

By 1974, Mr. Aiken had left the brokerage business and was working in market surveillance for the Toronto Stock Exchange, looking for rule breaking or shady practices. Friend and former trader John Manna – who started in 1965, when the trading floor still had spittoons for tobacco chewers – worked with Mr. Aiken and said the notoriously dapper dresser was immensely popular with everyone, from traders to secretaries to higher-ups.

"He was the jack of all trades," Mr. Manna said. "He knew everybody and everything. He was never an executive, but he was the go-to man."

A former colleague in the exchange's market surveillance department, Dorothy Hardman, said Mr. Aiken once hurt his leg but still insisted that she bring documents to his bedside at St. Michael's Hospital so he could keep working.

By the late 1980s, change was in the air. The Toronto Stock Exchange had actually invested in a computer trading system in 1977, even though its trading floor would not go silent for another 20 years.

In 1988, Mr. Aiken was among about 20 Toronto Stock Exchange employees who were unceremoniously let go by a newly installed vice-president of domestic trading at the stock exchange as part of an efficiency drive that some observers believed was the first nail in the coffin of the trading floor itself.

The firing of then 70-year-old Mr. Aiken, in particular, soured morale and outraged many stock exchange staffers, The Globe reported at the time, adding that rumours that he was escorted out by police were not true: An officer just happened to be in the elevator with him as he left.

Mr. Aiken launched a wrongful dismissal suit, but dropped it after he got a job with the OSC, where he would keep working for another 16 years, on contract after contract, in the investigations department, putting his long-time stock exchange knowledge to good use, talking to investors making complaints about brokers.

After selling his farm in 1996, he moved to a condo in Georgetown, Ont., with his partner, Edythe King. He commuted every day on the first GO train into town, said Joanna Fallone, his manager in the OSC's enforcement branch, and often arrived before any other staff.

"On paper I was his supervisor, but actually he was definitely a person who did his own thing," Ms. Fallone said. "He knew people personally. The rest of us had red tape to go through … He'd get a matter, and he would be able to just pick up the phone and just get an answer."

He decided to retire in 2004, he said, because he felt his memory fading. "He said he thought he was slowing down," Ms. Fallone said. "I didn't see it. … We just didn't want to let him go."

Two years after Mr. Aiken retired, the OSC named its case assessment department's meeting room after him.

Mr. Aiken leaves his daughter, grandson, partner, two stepchildren, four step-grandchildren and six step-great-grandchildren.

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