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The Oracle of Bay Street: finance bad boy Michael Wekerle is back, and his new firm is already the talk of Toronto

All in, Difference Capital had raised $100 million in three months. That’s no small accomplishment, for a number of reasons. One, it was summertime, a period when much of the reliable capital on Bay Street leaves town to frolic in Muskoka, Georgian Bay or other leisurely points east and west. Second, there’s no such thing as reliable capital these days—or whatever reliable capital there once was in Toronto has dwindled over the last few austere years. The remaining big money is controlled by a remarkably small group of tightly clenched fists. In short, it’s a tough time to be raising money, and Difference was now managing $220 million in assets.

There was plenty of booze on board Wek’s yacht. As it wound through the Toronto Islands, the boat’s speakers blared The Clash, David Bowie and U2. The boat made a pit stop at a marina and restaurant on Centre Island, and Wekerle hit the patio overlooking the docks, where he bought plates of poutine and onion rings and a round of tequila shots for his staff. There were a few other patrons seated on the patio, most of them seemingly bemused by Wekerle’s non-stop banter and the music echoing from the yacht.

But as the boat pulled away, two older couples sitting at a corner table started applauding, grateful to be seeing the stern side of Wek’s merry ship of fools. Wekerle yelled something cheeky back at them, but they couldn’t hear his raspy voice over the rising chorus of “Sunday Bloody Sunday.” They gave him a standing ovation.