Most Powerful People

Canada’s 50 Most Powerful Business People 2014: #11–20

Meet the dealmakers, string-pullers and master manipulators who call the shots in 2014

#11 Jeffrey Orr

CEO, Power FinancialKeeps the Desmarais fire burning

The late Paul Desmarais Sr. may have built Power Financial, but it’s the company’s CEO, Jeffrey Orr, who’s steering the ship. From atop Power Financial, Orr runs a vast empire of insurance and investment companies, which collectively oversee $188 billion in assets under management and more than a million life insurance customers in Canada and Ireland. Orr’s influence has grown in recent years: He’s now chairman at the majority of Power Financial’s subsidiaries.

#12 Pierre Beaudoin

President and CEO, BombardierKeeps calm and carries on

It hasn’t exactly been a quiet year for Canada’s most prestigious manufacturer. Bombardier finds itself under ever-increasing scrutiny for the innumerable delays keeping its long-awaited C series line of next-generation jets from taking off. Yet amid all the fretting, Beaudoin has remained a cool and confident leader, putting the company’s employees (of which there are nearly 71,500) at ease, along with—crucially—its investors. Much smaller problems than the calamitous C series rollout have spelled the end for many a corporation; that Bombardier is still a going concern—and a profitable one—is testament to Beaudoin’s influence.

READ: The inside story of Bombardier’s $4 billion-gamble on a super-quiet jet »

#13 Kathleen Wynne

Premier, OntarioIs luring business back to Ontario

Ontario is no longer Canada’s growth engine, but Kathleen Wynne is staying optimistic. The Liberal leader, who owes her thumping electoral victory in large part to fear of public-sector job cuts promised by the opposition Progressive Conservatives, has promised to govern from the “activist centre.” That includes the creation of a CPP-supplemented Ontario Retirement Pension Plan, a scheme that business lobbies have derided as a payroll tax. It won’t be smooth sailing for the charismatic political veteran—Ontario’s credit outlook was recently downgraded to “negative,” and it will be tough to meet her stated target of eliminating the province’s $12.5-billion deficit by 2018. Wynne will have to hope that a 10-year, $2.5-billion Jobs and Prosperity Fund of corporate grants will lure business back. The government’s success in attracting Cisco’s new R&D expansion to Ontario suggests it might just work.

READ: Here’s the basic math error that ruins Tim Hudak’s Million Jobs Plan »

#14 Alain Bouchard

Founder, Alimentation Couche-TardCould become the world’s convenience-store king

He’ll step down as Alimentation Couche-Tard’s president and CEO in September, but Alain Bouchard won’t be letting up. With more than 11,300 stores in North America, Europe, Asia and Latin America, and a current market capitalization of $16.8 billion, Bouchard (who’ll continue as executive chairman) is still looking to grow his convenience store empire. After his acquisition of Norway’s Statoil Fuel & Retail, Bouchard’s biggest deal yet, he’s looking to the U.S., where the landscape is mostly regional chains—all potential opportunities for the self-made Quebec billionaire.

READ: How Couche-Tard conquered the world, starting with a single dépanneur »

#15 Jim Pattison

CEO, Jim Pattison GroupHas twice the ambition and connections of CEOs half his age

At 85, he’s the oldest member of the Power 50, but he’s showing no signs of slowing down. “I work and travel as I’ve always done,” says Jim Pattison, speaking from his office in Vancouver. That’s a bit of an understatement: His many-tentacled Jim Pattison Group keeps growing, often aggressively. Its Overwaitea Food Group has bulked up, snapping up 15 former Sobeys locations and opening others from scratch. In July the Pattison Broadcast Group bought nine radio stations from Rawlco. Last fall it took juice maker Sun-Rype private. And over the past year the company got into an entirely new line of business, buying a pair of farm equipment dealers with 16 locations across the Prairies. “We like the future of Western Canada. We think that agriculture, long term, has a good future, particularly when you see what’s happening in Asia,” Pattison ventures to say (more than he’ll typically reveal about his company’s strategy). What Pattison says publicly is seldom as interesting as what he does, however, such as making Glen Clark, the former B.C. premier who many blamed for the province’s “dismal decade” of economic stagnation, his group president and, along with deputy chairman Michael Korenberg, heir apparent. Some of the country’s most rarified networking still goes on aboard his 46-metre yacht, the Nova Spirit. You can bet that when a big decision is made, Pattison is only a phone call away.

READ: Jim Pattison, the Warren Buffett of B.C. »

#16 Frank McKenna

Chair, Brookfield Asset ManagementIs a Human LinkedIn

As a former provincial premier and U.S. ambassador, he’s rubbed shoulders with Bill Clinton and George Bush. As deputy chair of TD Bank Group and chair of Brookfield Asset Management, he sits at the table with Canada’s blue-chip elite. As a regular at the Bilderberg conference for global business leaders, and host of his own annual summit at Fox Harb’r, a Nova Scotia resort, he talks to the masters of the universe. Rumour has it, they listen.

#17 Joe Oliver

Federal Minister of FinancePlans to make his own mark

His predecessor held the job for eight years; Oliver has been Finance Minister for six months. No matter how long he fills the position, the former investment banker’s political reputation will always be linked to Jim Flaherty. Still, the Conservatives view the promise of a balanced budget by 2015 as key to winning re-election. Flaherty made the commitment—but Oliver will deliver it.

READ: Joe Oliver’s resume shows he shares Flaherty’s views on a national securities regulator »

#18 Hunter Harrison

CEO, Canadian Pacific RailwayRewrote the rules of transport

The brash Tennessean with the bourbon-drenched voice is transforming CP: Once the worst performing railway in the industry, it now has a chance to become one of the best as it adapts to Harrison’s ultra-efficient “precision railroading” strategy.

READ: Top Turnaround CEO of the Year: Hunter Harrison, Canadian Pacific Railway »

#19 Monique Leroux

Chair, President, CEO, Desjardins GroupIs putting a little Quebec bank on the map

Most Canadians outside Quebec probably know Desjardins solely from its car insurance ads, but the Desjardins Group is Quebec’s biggest private employer—and the second-safest bank in the world, according to Bloomberg. Head honcho Monique Leroux has built the network of credit unions into a financial powerhouse with $212 billion in assets via cautious plays and smart deals, such as the January acquisition of State Farm’s Canadian unit to further the company’s western push. Canadians should hope that some of Leroux’s considerable success will rub off closer to home: She was appointed to Finance Minister Joe Oliver’s Economic Advisory Council in July.

READ: The question of quotas on corporate boards »

#20 Don Drummond

EconomistGets quoted even when he’s in silent mode

His name appeared more often in the pages of the Toronto Star, Globe and Mail and National Post during Ontario’s recent election than the leader of the Green Party’s did—and Don Drummond wasn’t even doing interviews. The former TD Bank chief economist stayed silent as campaigning politicians endlessly cited his landmark report on the province’s public service. With more than three decades of experience at TD and Finance Canada, he is the country’s most sought-after expert on the intersection of economic issues and public policy.

READ: Drummond report on government spending falls short »

Continue to #21–30 »