Since he was in the fourth grade, Hugh O’Reilly dreamed of becoming a lawyer. A dream that—at least in part—stemmed from television’s romanticized portrayal of the profession, as well as his father’s wistful regrets of his legal path not taken.
“My father was a doctor, but he always talked about how he wished he went to law school,” Hugh explains.
As Hugh got older, he developed aspirations of becoming a politician—and noticed that the law was a popular starting point for many of Canada’s greatest.
“When I started university, I wanted to become a lawyer, but then I fell in love with student politics,” he says.
In a quest to realize his political aspirations, he opted to pursue graduate school at Carleton University in Ottawa and then moved to Toronto to work for a Member of Parliament for a couple of years. It wasn’t exactly what he’d expected.
“In grad school, I found I wasn’t enjoying politics as much when engaged at that intensity,” he admits. “My job working for the MP wasn’t terribly fulfilling, so—having done well enough in undergrad and grad school—I went back to my original plan and decided to apply to law school.”
A strong starting point
Hugh started attending law school in 1987, and quickly discovered he really enjoyed its problem-solving and technical components. In 1993, after articling in Calgary and working as Chief of Staff to a cabinet minister in the Government of Ontario, he joined Osler as an articling student.
“As a student, my rotations were corporate, litigation, and pensions and benefits,” he explains. “I was hired back to the pensions and benefits group as an associate, where I did everything from working on surplus opinions to helping out with pension litigation.”
While his time at Osler was short—only 18 months—the lessons he learned there have stuck with him throughout his career.
“One thing Osler taught me, beyond a commitment to hard work, was the importance of being practical and client-focused. Doing a great job for clients, understanding and meeting their needs within the boundaries that are permissible, coming up with practical solutions—I learned all of that at Osler.”
While Hugh practised at other law firms throughout his career, he holds a debt of gratitude to Osler.
“The friendships I made there have been enduring. No matter where I was, the people at Osler went out of their way to help me in my career,” he says.
In 1995, Hugh was approached by Canada Trust with an offer he couldn’t refuse—an opportunity to work on the business side of an organization.
“There’s a lot to learn in the practice of law and, for some reason, after 18 months at Osler I had this idea in my head that I was stale and not meeting expectations,” he recalls.
“When Canada Trust head-hunted me, I was excited for the opportunity. I went into their law department as the senior corporate counsel—and it was a great experience.”
During his tenure at Canada Trust, Hugh expanded his knowledge about holding assets in trust, the Canadian Depository for Securities and transactional work. But after a while, the long hours got to him, and—after some convincing from his wife—he decided that, if he was going to work that hard, it might as well be at a firm. So he joined Torys LLP in Toronto in 1996 and became a partner before leaving for Cavalluzzo Shilton McIntyre Cornish LLP in 2002.
“My wife and I adopted two kids, ages three and five at the time, in the late 1990s. While Torys allowed me to take a parental leave—which was quite rare at that time—when I returned I was still logging a lot of hours and not spending a lot of time with my family,” he recounts. “It was around that time that I realized these kids didn’t ask me to be their parent—I volunteered for the job. So I thought going to a smaller firm would allow more time for that.”
During his time at Cavalluzzo, Hugh launched the firm’s pensions and benefits group, eventually adding insolvency a few years later. He recalls his time there as being thoroughly enjoyable—allowing him to exercise his skillsets, develop a practice from the ground up and try his hand at insolvency work. He even had an opportunity to argue a case before the Supreme Court.
It was during this time that he also met his current employer, OPTrust—an organization that invests and manages one of Canada’s largest pension funds and administers the OPSEU Pension Plan.
“I developed a practice at Cavalluzzo that focused on advisory on pension plans, and OPTrust was a client,” he says. “So I learned how their pensions operate and how to invest them, as well as how to translate communications between senior management and the board.”
Hugh became so familiar with the organization that, when the CEO of OPTrust resigned, a number of people in the pension industry suggested to Hugh that he apply for the job.
“I was a senior partner at Cavalluzzo. I had an amazing practice, and I didn’t have a boss. So I had to think long and hard about moving to OPTrust. Eventually, I put my name forward and shared my vision regarding what I wanted to do and how I wanted to do it, and ended up getting the job.”
Today, Hugh typically starts his days at 4:55 a.m.—making sure to fit in a modest workout and a 20-minute walk before sitting down at his desk around 7:20. Being in charge of a large pension fund, he’s responsible for ensuring it’s fully-funded at all times, so as to meet member expectations. While he’s the first to admit it’s hard work, it’s also anything but boring.
“When I’m in the Toronto office, I often meet with my direct reports and deal with issues ranging from how to deal with pension administrators, to our investment activities, to HR or IT issues, to our integration agenda,” he says.
“What’s great is that the variety is unbelievable. I deal with four to five different things a day—and all kinds of interesting people, like Tony Blair. It’s fun.”
Hugh expects to retire within the next five years, but he doesn’t expect to stop working. While retirement will afford him more time for leisure activities—primarily reading, watching TV and driving around in his two babies, a Cadillac Coupe and Lincoln SUV—he also plans to do consulting work around retirement security issues.
Thanks to the versatility of his law degree, anything is possible. When reflecting on his current job and the path it took to get him here, Hugh realizes the core things that got him interested in the law—the ability to solve problems, identify issues, uncover appropriate solutions—are skills that are in high demand in today’s economy. And they’re skills that all lawyers have.
“I think lawyers are really well positioned for the innovation economy—and that’s important to remember. When you get handed something you’re unfamiliar with, recognize that you have the skills to tackle it—and take on whatever challenge is in front of you. Because you never know how things will work out.”