Wekerle was born in Toronto and attended York University for a year before dropping out to work on Bay Street. In 1982, he scored a job on the floor of the Toronto Stock Exchange with a long-forgotten firm. He spent a lot of time fetching bagels and coffee for other traders. “I’d have, like, 17 different orders, and if I fucked one up, I wouldn’t hear the end of it,” he says. When the firm downsized, he asked for a job from the head trader at First Marathon Securities, who told Wekerle he could have a job if he lopped off his unkempt mane and returned within 15 minutes. That haircut essentially launched his career.

Inside of a few years, Wekerle had moved from the trading floor to the desk. In simple terms, he was a matchmaker, putting together buyers and sellers of big blocks of stock. If he couldn’t find a buyer, Wekerle would use the firm’s own money to purchase the block until one could be found, a practice called liability trading. It’s often used as a loss leader designed to bring more business to a firm, and Wekerle brought in business like no one else. His gregarious personality had quite a bit to do with it, and he socialized a lot. “He’s the guy who knows everyone, and everybody likes Mike,” says Cindy Tripp, a fellow trader at First Marathon. “You’ll never have a bad time when you’re with Mike Wekerle.” With so many connections, he always had a line on who was interested in acquiring or shedding stakes in companies. Then there was his famous ability to multi-task. “It was not uncommon to see him on the desk working two phones, barking orders at a trader and giving personal financial advice to his friend who might be sitting there,” says Henry Kneis, who worked with Wekerle at First Marathon and is now Difference Capital’s chief financial and operating officer.

But the real key to Wekerle’s success as a trader is his gargantuan memory. He carried around the details of countless trades and knew who owned what and how much of it. “There is a bit of a savant element to his brain,” Kneis says. Wekerle’s mental catalogue of the market proved to be a tremendous advantage in locating buyers and sellers. (Despite his prodigious memory, Wekerle has a habit of losing things and wears his house key around his neck.)

Word about Wekerle travelled fast, and one person who took notice was securities lawyer Eugene McBurney. Along with Brad Griffiths, head of investment banking at Gordon Capital, McBurney wanted to start a new financial firm. There was only one person McBurney wanted to run the business’s trading operations. Wek joined the company, then called Griffiths McBurney & Partners, in 1995, a few months after it formed. Kevin Sullivan, another First Marathon employee, came with him to run the sales side. Together, the four of them built what would become GMP Securities. A handful of colleagues from First Marathon, including Tripp, defected to the new firm, which immediately became one of the biggest block traders on Bay Street. GMP also worked on some historic deals, such as co-leading the IPO for Research in Motion in 1997.

Wekerle continued his prolific streak, and the mystery around his abilities grew. McBurney once asked a client what made Wekerle such a great trader. “He just makes you do stuff you don’t want to do,” the client said. McBurney stresses that Wekerle wasn’t simply a guy taking orders from buyers and sellers; he was constantly coming up with investment ideas for clients. “Most of the time he was right,” McBurney says. One of his most legendary calls was foreseeing the commodities bull market early and pushing clients toward resource stocks.

For Tripp, Wekerle was an ideal boss. “He treated me fully like a professional. I never felt like I was paid less or wasn’t promoted because I was a chick,” she says. When Tripp was pregnant with her second child, she approached Wekerle about job-sharing with another woman on the desk. Wekerle agreed to the arrangement without thinking twice.

As his career took off, Wekerle’s good-natured personality never changed. “I’ve seen successful, wealthy guys who are just pricks,” Kneis says. “They think their wealth gives them the right to mistreat people. Michael doesn’t do that.” Wekerle is the kind of guy who will always pick up the bill, tip generously and treat the server the same way he would a CEO. He’s active on the charity circuit and is a big supporter of Toronto’s Centre for Addiction and Mental Health and the Seeds of Hope Foundation, a community outreach program. He even paid to send one teenager he met through the program to Morehouse College in Atlanta, where tuition, room and board runs upwards of $40,000 per year.

There are smaller gestures, too. Wekerle helps one of his friends, Spencer Miller, who has cerebral palsy, with living expenses. For one of Wekerle’s birthdays, he flew Miller and dozens of friends to the Bahamas for a private concert with Vince Neil of Mötley Crüe. “Mike has a reputation as being a wild and crazy guy,” Miller says, “but he’s one of the nicest, big-hearted individuals you’ll ever meet.” Tripp says Wekerle couldn’t hold a grudge if he tried, which is probably true. During one interview, Wekerle let loose on another Bay Streeter (the words “fake mother­fucker” were uttered). When asked later, he shrugged it off. “It was probably the mood I was in that day,” he said. “Water off a duck’s back.”

Around the same time as the financial market turmoil in 2008, Wekerle’s home life grew complicated. His marriage to his second wife, Lea-Anne, with whom he was raising five biological kids and one foster child, had come under strain. But there were worse things to come. In March 2010, the family was vacationing with friends in Los Cabos, Mexico, when Lea-Anne left early to head home. When Wekerle returned to Toronto with his kids, he was told by one of his sisters that Lea-Anne, who was taking prescription medications, had died of a heart attack.

The news sent Wekerle into a tailspin. “I ended up looking to drinking more aggressively in those days and kind of went by in a fog,” he recalls. Sometimes he wouldn’t get out of bed until noon, and he wasn’t much interested in GMP. A trip to Arkansas that fall resulted in a lawsuit, when Wekerle allegedly blew an air horn in a hotel lobby, tossed money from a fanny pack into the air, dropped his pants, licked a woman’s foot, made lewd comments and injured a valet when he tried to carry the man on his shoulders. (The suit, filed by the valet in 2013, is still before the courts. Wekerle’s legal team has dismissed it as frivolous.)

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Meanwhile, things were changing at GMP. “I had some views about the expansion of the firm that were different from others’,” he says. “My old partners who started the firm with me were no longer there, and I felt the isolation and the loss of my wife made my role as a producer more difficult for me.” The era of the star trader was over, too, as more market activity was handled by computers. Trading commissions had fallen significantly. Wekerle’s colleagues were worried about his behaviour and subjected him to urine testing. His departure seemed like only a matter of time. In June 2011, gossip magazine Frank posted a video to its YouTube channel of a charity roast for Halifax businessman Rob Steele, a close friend of Wekerle’s. The video shows an unsteady Wekerle trying to commandeer the microphone from host Rex Murphy before being escorted offstage. By August, Wekerle and GMP had parted ways.

Wekerle talks about Mother’s Day 2012 as a turning point. “That was a tough fucking day for me,” he recalls. Wekerle learned that his two youngest kids had sat at the back of the classroom in school colouring instead of making Mother’s Day cards. He began the process of ridding himself of people he thought were negative influences and sought help to deal with his depression. “People are really afraid and embarrassed to go see someone,” he says. “It’s very important to understand there’s no difference between breaking a leg and having a meltdown. It’s time to recover.”

Even before that day, Wekerle had been plotting his next move.

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