The day of Wekfest 2014, the annual charity rock concert hosted by Michael Wekerle at his home in Caledon, Ont., a team of police officers is stationed at the bottom of his driveway to direct traffic to a nearby field for parking. There, a crew of black-shirted valet attendants hops to action in the mid-August sun, while a shuttle bus whisks visitors to the main event at Wekerle’s sprawling 80-hectare property. Everyone wears a wristband: pink for regular admittance and green for VIP access, which costs $500. There is very little pink to be seen. At the centre of the yard is a massive stage, where some of Wekerle’s favourite bands will play, including Our Lady Peace, 54-40 and Sloan.

(Photo: Matt Barnes)

Many of his Bay Street friends and colleagues are in attendance, though the crowd appears predominantly young and attractive, suggesting that at least some Wekfest supporters have opted to give their green wristbands to their kids. A team of waitresses in short skirts and bikini tops ensures no one is without a drink, while a row of food trucks serves up ice cream and grilled cheese sandwiches alongside Wahlburgers, the fast-food chain Mark Wahlberg owns with his brothers. (Wekerle is an investor.) As for Wekerle, his booming voice, already hoarse, can sometimes be heard before he’s even seen, as he whips around the property in an electric golf cart, shouting incomprehensible greetings to his friends. He’s wearing black high-top sneakers, a pair of faded skin-tight jeans and, of course, an official red Wekfest 2014 tank top. At 50 years old, Wek (everyone calls him Wek) looks more like an aging rocker than a guy who works in finance.

It’s still early in the afternoon when Wekerle peels off the tank top and climbs into a boxing ring set up for a charity match, exposing a torso adorned with tattoos. There’s a heart inked on his chest, a peace sign on his neck and the iconic Rolling Stones lips-and-tongue logo on his left bicep. He’s not slated to box, but as his bemused executive assistant explains from the sidelines, “He just had to get in the ring.” Wekerle hurls himself against the ropes like a professional wrestler before launching into the air, his gloved fists raised in triumph.

Let’s pause here and savour this image. Because, in many ways, Wekerle is on the verge of something big. Some would say we’re witnessing the second coming of Wek. He already has a well-earned reputation as perhaps the greatest trader Bay Street has ever seen, and his freakish talent for playing the markets has made him (and a host of other people) very rich. But he also spent two years lost in a dark place, grappling with a devastating personal loss and being spurned by the capital markets firm he helped make great. It was not that long ago that he found his way out. He has a new venture, Difference Capital Financial, a merchant bank he co-founded in 2012 to invest in privately held, late-stage tech, health-care and media companies. And starting Oct. 15, he will embark on his highest-profile gig yet: the newest dragon on CBC’s hit show Dragons’ Den. He’s already a legend on Bay Street, and soon every small business owner and mompreneur from Victoria to St. John’s will know (and probably love) Wek.

More: Meet the New Cast Members of Dragons’ Den »

The show’s producers sought him out to replace their biggest star, Kevin O’Leary, who announced in March that he would not return for season 9. Wek accepted the offer because he wants a larger platform for his company, for the charities he supports and for himself. “This takes me from Bay Street to Main Street,” he told me. The CBC is betting that Wekerle will be a hit. He already figures heavily in the promos, looking like the very definition of a business rock star in his flamboyant blue floral jacket and flowing hair. He’s a natural on camera, too; the producers were impressed by his ability to think long-term about the investment pitches, despite having the appearance of a guy who lives entirely in the moment. The only thing he had to work on was slowing the torrential pace of his speech.

And so, if it’s possible to encapsulate this moment of Wekerle’s life in a single image, the one of him shirtless, joyous and hanging in mid-air at his own party is a pretty good one. Still, it’s not entirely accurate. That new firm, Difference Capital, isn’t yet ascending along with him. The stock has dropped 70% since it debuted in 2012, and two of the company’s highest-profile investments are also its most troubled. In August, Difference started pruning its portfolio. Wekerle, for whom success as a capital markets rainmaker came naturally, has some of his hardest work ahead of him.

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