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Nicknamed “the Piranha,” Jimmy Connacher ran the most innovative and notorious firm on the Street. Goldon Capital pioneered block trades and bought deals, and rewarded itself with heaping helpings of booze and bling. Buy by 1993, it was all over (John McNeill/The Globe and Mail)
Nicknamed “the Piranha,” Jimmy Connacher ran the most innovative and notorious firm on the Street. Goldon Capital pioneered block trades and bought deals, and rewarded itself with heaping helpings of booze and bling. Buy by 1993, it was all over (John McNeill/The Globe and Mail)

When big personalities and gut feelings ruled the markets Add to ...

Since our inaugural Top 1000 issue in 1984, Report on Business magazine has been reporting on the highs and lows in business, from around the world. Some of the juiciest stories, however, were the ones we never reported. Read all 12 articles here.


Not long ago, Canada’s stock market was dominated by a single, larger-than-life personality. The name changed with each generation, but there was always one trader who was cock-of-the-walk, who possessed an uncanny ability to read the Street, who barked buy-and-sell orders that rivals rushed to match, and whose excesses outside of work were as legendary as the paydays earned on the trading desk.

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In the 1980s, when the cult of equities was just getting rolling, that gunslinger was Jimmy Connacher, head honcho at Gordon Capital. Jimmy was “the man” because he and his partners had turned their backs on the genteel club that dominated Bay Street. Gordon offered up its own capital to get deals done, rather than living comfortably on commissions. Jimmy invented the “block trade” and “bought deal,” which saw Gordon buy shares from institutions or corporations, and shoulder the risk of selling them on to investors.

When it worked, and it usually did, Jimmy’s crew made more money than anyone else – millions a year, when a million meant something. But the Gordon team also risked everything on their bigger trades, and you’d occasionally hear of partners remortgaging their homes to prop up the firm after a deal went sour. Going all in with his own money won Jimmy the respect of a community that came to emulate his approach, if not his style.

That style was one of a renegade outside of work, as well as on the trading desk. There is a tale of Jimmy showing up at a snotty Christmas party wearing nothing but a string of lights. There was the time Jimmy and his buddies bought matching Jaguars after one particularly good month, only to return every car after one of the guys got lousy service from the dealership. And there were the parties–legendary bashes that often started within the office, where a butler named Basil brought traders martinis on a silver tray as the day wore on.

Jimmy burnished his legend by rarely talking to the press. In the handful of times I talked with him, he had all the warmth of an angry Doberman–tightly coiled, curt and dismissive when answering questions on how he and Gordon could keep their edge against increasingly large and aggressive rivals. The charm, however, was also apparent: During one interview, Jimmy offered to have Basil fix me a Bloody Mary. It was 10 a.m.

The last time I saw him was in 1993, at an Ontario Securities Commission hearing that saw Jimmy banned from the investment industry for three months, a trip to the penalty box that spelled the effective end of his reign. That day, the defiance was gone.

Jimmy’s title of top trader went to Lawrence Bloomberg in the 1990s. The First Marathon founder matched Jimmy’s savvy and intensity on the trading floor, but Bloomberg was restrained and approachable outside of work. By the late 1990s, Mike Wekerle at GMP Securities assumed the mantle as “the guy,” and Wek, as he’s known, had the tattoos and private-jet-with-Mark-Wahlberg lifestyle that ensured a trader was once again the talk of the town.

Today, big banks and high-tech systems dominate trading, not big personalities and a gut feel for markets. Trading desks are run by risk managers, with zero tolerance for Jimmy’s all-in approach to a big deal. The gunslingers are gone. They sure were fun to watch.

Andrew Willis worked in business journalism for more than two decades, including 15 years chronicling the fun and games in Canada’s financial community as The Globe and Mail’s inaugural Streetwise columnist. He is now an executive at Brookfield Asset Management.

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