Six years ago, Rocco Rossi walked into a job interview with one of the most buttoned-down business organizations in the country wearing a blue-plaid suit and plaid tie — not exactly the look the Ontario Chamber of Commerce had in mind for its next chief executive officer. But Rossi was coming from a promotional event for Prostate Cancer Canada, where he was then working. They were asking participants to “Wear Plaid for Dad.”
As the interview with the OCC continued, someone on the panel told Rossi, “You realize in this job, you may have to take on the government of Ontario rather publicly?”
That didn’t seem to be a problem. “What part of a guy showing up in a blue-plaid suit suggests I’d be too shy to take on the government?” he asked.
He got the job.
Six years later, Rossi has just finished his tenure with the chamber, and although he’s a couple of weeks shy of his 62nd birthday, he wants everyone to know: “I’m not retiring — I’m rewiring. People keep wishing me well on my retirement. It’s kind of pissing me off! I don’t know anyone ready for retirement who’s about to do a 1,000-kilometre walk.”
Yes, by the time you read this, Rossi will have left to go on what’s become his go-to pilgrimage: walking the 1,000-kilometre-long Camino de Santiago, in Spain.
Rocco Rossi (left) with Daniel Tisch, the new president and CEO of the Ontario Chamber of Commerce. (Steve Paikin)
Rossi has experienced one of the most up-and-down careers of any public figure in Ontario. He’s been at the Boston Consulting Group and an executive at Torstar and Interbrew. He helped turn around a failing start-up and brought significantly more attention to the problems of heart and stroke disease and prostate cancer by heading up non-profits focused on those issues.
But his biggest success has been with the chamber of commerce, where he doubled revenues and helped convince the provincial government to bring in major supports for businesses during the worst of COVID — and this happened in weeks rather than the years those policies would normally take to implement.
But, true to his word when he had his job interview wearing plaid, Rossi took on the government when he felt it was offside. For example, during the worst of COVID, the province allowed big-box superstores to remain open, while forcing small businesses to close. The policy seemed ridiculous, since customers jam-packed the big stores and ignored social distancing. Smaller businesses, fighting for their livelihoods, complained to no avail.
“But we did it in a thoughtful, methodical way against the Ford government,” Rossi says.
Graham Henderson, then on the OCC board, says, “His engagement was all-in.”
Publicly chastising a pro-business government can be tricky for business lobby groups. “You have to pick your spots,” Rossi admits. “You can’t criticize them all the time or support them all the time or they tune you out.”
But that wasn’t the most dramatic public brouhaha on Rossi’s watch. During the Ford government’s first year, then-finance minister Vic Fedeli wanted to blow up the Beer Store’s master-framework agreement with the province in hopes of getting more choice for consumers. Rossi says he told Fedeli, “Minister, you can decide to tear up the agreement, but not without compensation. We’ll have to come out against you. Contract law is pretty important to business.”
Fedeli went ahead anyway, attempting to end the MFA without compensating the breweries. Next thing you knew, Rossi was taking his campaign to the newspapers. Then the U.S. Chamber of Commerce weighed in, saying the province’s move risked “sending a negative signal to U.S. and other international investors about the business and investment climate in Ontario.” Others said Fedeli’s move would flout the World Trade Organization rules.
Fedeli was furious and called the chamber demanding Rossi’s ouster. But Rossi held firm: “If we don’t stand for the right of contracts, we stand for nothing,” he told the board, which backed its CEO. Next thing you knew, it was Fedeli who got bounced out of finance after just one budget.
“But to be clear,” Rossi continues, “we made up, and we did lots of great things together in his new role at economic development,” where Fedeli has been the minister since June 2019.
Everything about Rossi is big. He stands 6 feet 3 inches tall but looks taller. When he speaks, his voice booms. His personality is similarly huge and, on occasion, gets him in trouble. He admits that, very early in his tenure, he had too much to drink one New Year’s Eve; in an attempt at some self-deprecating humour, he tweeted out a picture of a bottle of champagne with caviar-covered cake. The copy said: “Celebrating New Year’s the 1-percenter way! Let them eat cake:-).”
Twitter exploded. The OCC board hauled his ass in on the carpet and forced him to apologize. But, ultimately, the chamber stuck with him.
“I paid back my bonus,” says a contrite Rossi, who learned that not every attempt at satire flies on Twitter.
Some of Rossi’s toughest career moments have come during his engagement in partisan politics. As a teenager in the 1970s, he found himself at a Progressive Conservative party event in Don Mills, where future senior Ontario cabinet minister Dennis Timbrell was the MPP. Someone at the event said something pejorative about newcomers. Even though Rossi was born in Toronto, he instinctively felt targeted by the comment. “I’ve got vowels at the end of both of my names,” he says.
Rossi says that Timbrell, to his credit, pulled him aside and said, “Rocco, that doesn’t reflect my views, and I’m trying to change the PC party to get this kind of thing out of the party. But we’re not there yet.” Timbrell suggested that, if Rossi wanted to stay involved in politics, he should maybe check out York East Liberal MP David Collenette’s campaign. “You might feel more comfortable there,” he said. Rossi did just that, and for more than the next three decades, the Liberal party was his political home.
In 2010, he and some advisers gathered at the appropriately named Rocco’s Plum Tomato restaurant in Etobicoke in hopes of mounting a bid for the vacant mayor’s chair in Toronto. The idea was to run a campaign uniting moderate Liberals and Conservatives with a dash of populism to boot. Mayor David Miller’s second and ultimately final term had been waylaid by a protracted garbage strike, prompting Rossi’s team to urge that he run on the slogan “It’s time to take out the trash.” It played on both the garbage strike and the need to clean house at city hall.
Inexplicably, Rossi rejected the slogan.
Then when his team told him both Mike Harris and Mississauga mayor Hazel McCallion were prepared to endorse him, he turned thumbs down on that, too, figuring the former premier was still too toxic in the 416. Instead, a veteran councillor named Rob Ford got into the race, ran on “stopping the gravy train,” and the rest is history.
What does Rossi now think when he looks back at that campaign? “I’m just an idiot,” he says. “Rob caught the public’s imagination.”
Rossi peaked at 16 per cent in the polls, then sank. Eventually, he dropped out.
But there was a provincial election the following year. Long-time Conservative backroomer John Capobianco brokered a meeting between Rossi and then-PC party leader Tim Hudak. The pair agreed Rossi should contest the swing midtown Toronto riding of Eglinton–Lawrence. As he launched his campaign, Rossi tried to make the point that he wasn’t leaving the Liberals — they’d left him years ago with policies he thought were too interventionist. But jilted Liberals from all over Toronto were furious and descended on Eglinton–Lawrence to help defeat Rossi. They succeeded. Liberal Mike Colle garnered a nearly 8,000-vote margin of victory.
“That race cost you a lot of friends,” I say to Rossi.
“It didn’t cost me the friendship of anyone who was a real friend,” Rossi responds.
Rossi wears his emotions on his sleeve, and there’s no greater example of that during our conversation than when he discusses the death of his friend Don Kitchen, who was president of Labatt Brewing and an executive vice-president of Interbrew, where Rossi was also an executive. In August 2000, Kitchen had a heart attack while on business in Brussels and died at age 44. Four years later, Rossi became CEO of the Heart and Stroke Foundation of Ontario, determined to find ways to allow people to survive heart attacks. One idea was to put a defibrillator in every Ontario arena, where too many older guys trying to recapture their hockey-playing glory days suffer heart attacks. As part of a promotion, Rossi cycled 1,900 kilometres from Rainy River to Toronto to raise money.
One day, a man was attending an event at Copps Coliseum, in Hamilton (now called FirstOntario Centre), when he collapsed from a heart attack. Happily, because of the Heart and Stroke program, there was a defibrillator in the arena. The man’s family later told Rossi, “He survived because of you. Now we’ll have him for Christmas.”
Rossi is holding back tears as he tells the story. And here’s the kicker: the name of the man in Hamilton whose life Rossi’s program helped save was Don.
After Kitchen’s death, Rossi found himself on a Toronto subway car when the enormity of it all overcame him. He began to cry uncontrollably. There was a discarded newspaper on the seat beside him, opened to an article about the Camino de Santiago. That was Rossi’s eureka moment. He resolved to walk the Camino to clear his head and recharge his batteries. He’s now doing it for the 18th time.
No one seems to know what Rossi’s next mission will be, including Rossi himself. But I’m betting this:
It’ll be big.
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