From a wallop of camaraderie on the arm to annual lunches with the former CEO of Manulife

During one of the many interviews I conducted with Dominic D’Alessandro when I was researching my 2009 book on Manulife, we stood looking at a painting he’d chosen from the corporate collection for his office. Created by 20th-century Canadian artist Jean Paul Lemieux, it was called “La nouvelle France.”
In the foreground was a seated woman in black, holding a baby. Standing close was a young girl in a long red dress and a white hat. Behind, the land sloped away into a valley of tree stumps. “A lot of people don’t like this painting,” said D’Alessandro. “They see religious overtones.”
He waited for my reaction. “She looks like a hard-working mother,” I said. “And the land has obviously been cleared for farming.” D’Alessandro whacked my upper arm with the back of his hand, and said, “To me, it’s all about the immigrant experience. That’s what I’m all about, too.”
Being a chief executive officer is not a contact sport. Among the many business leaders I’ve interviewed, no one else ever delivered a message using such physical means. “It’s only the last 10 years that I realized how thoroughly my personality, character and attitudes have been shaped by the experiences I had as a child.”
D’Alessandro didn’t enjoy the privileges of Montreal’s Westmount or Toronto’s Rosedale. Born in Frosolone, Italy, he rose through the ranks on merit alone. His father, Anthony, left Italy in 1949 to work in Montreal, saved his money, and sent for his wife, Angelina, and their children. Shortly after they arrived, Anthony died in a construction accident, when D’Alessandro was just six. Angelina raised four children in Little Burgundy, a disadvantaged neighbourhood of cold-water walk-ups. For income, she rented the house next door and filled it with boarders, mostly Italian men who’d moved to Montreal ahead of their families.
D’Alessandro spoke Italian at home, learned English at school and French in the streets, where most boys didn’t have the same yearning to get ahead. That background also established his caring view toward those less fortunate. “I’ve always been sympathetic to the underdog,” said D’Alessandro. “If I categorize myself, I’d certainly be left of centre. I find it very facile for people to prescribe for others. A lot of very successful people, because the system has worked well for them, are remarkably unsympathetic. They don’t make allowances that maybe they were successful because they had some gifts. If they’d just been average, they’d still be there, shining hubcaps.”
D’Alessandro graduated from Loyola College, became a chartered accountant, worked for various companies, then joined Royal Bank in 1981. “I never felt inferior to anybody, anybody, even though I should have because I didn’t dress as well, I wasn’t polished. I felt the opposite.” Whenever he attended receptions on the 50th floor atop Royal’s headquarters in Place Ville Marie, he’d walk to the window, look down at Little Burgundy, and ponder just how far he’d come.
In 1994, D’Alessandro was named CEO of Manufacturers Life Insurance Co., with 30,000 employees and agents in 15 countries. At five-foot-seven, D’Alessandro’s size would never dominate, but there’s an arresting aspect to his beetling black eyebrows, distinguished grey hair and spring-loaded step that radiates self-confidence. He seems to emit electricity from some internal source.
Nor was D’Alessandro afraid to speak his mind where others waffled. At the Manulife annual meeting in 2000, D’Alessandro castigated his fellow CEOs for laziness. “Those of us who are supposed to lead some of Canada’s most significant enterprises haven’t been doing our jobs. As a group, we have been far too timid and cautious. We have been too slow to innovate and slow to seize global opportunities.”
As if to prove the point, in 2004 Manulife paid $15 billion for Boston-based John Hancock Financial Services, creating the largest life insurance company in North America. With that deal done, and after piloting the firm through the market troubles of 2008-09, he retired. “I’m very proud that I’ve come so far. I have a very good appreciation of where I started off and the circumstances of my family,” he told me. “It’s one of the reasons I’m so besotted by this country; I’ve been well treated by it. I’ve made lots of money, more than I ever expected and more than I’ll ever need, and I think conducted myself in a way that reflects well on me, my family and my values.”
It’s stating the obvious, but needs saying: Immigrants work harder than homegrown Canadians. They have something to prove to others and to themselves. Humble roots into powerful trees do grow. D’Alessandro and I have since become friends. After all, how can you not like a guy who emails from Florida in January to say he’s already got topics in mind for our annual summer lunch in Toronto?