Paul Riley on storytelling, his two careers and what he owes his immigrant mother

Lunch with Roderick Benns: Conversations with interesting people in Kawartha Lakes

His pint of Turbo Hazy Hot Rod clinks with my own pint of Lock 33 at the Pie Eyed Monk. We’re easily the most overdressed patrons in the pub but my lunch companion wouldn’t want it any other way. You’d have more success in glimpsing a yeti on Kent Street than you would in spotting Kawartha Lakes divorce lawyer Paul Riley without an immaculate suit on.  

That’s not an attitude from growing up with a silver spoon in his mouth. Rather, it’s the classic second-generation Canadian story, in this case born of a hard-working immigrant mother from Jamaica who saw a better life for her son in the cold north than what she saw in her community of Trench Town.

“My mother went to school with Bob Marley,” Riley says of the reggae legend’s hometown. “While the world embraces Bob Marley, my mother just says ‘Aw, he’s all right,’” he says laughing.

Riley, 55, and a father of four, moved to Canada when he was nine. But there were some tough years before that, considering his mom left him in the care of his grandmother in Jamaica when he was just four years old. He wouldn’t see his mother for five long years. That’s common practice in Caribbean nations where parents — usually the mother — strike out for Canada or the U.S. in search of a better life for their kids, who stay with a member of the extended family back home. “It’s almost always the grandmother. Jamaica is a very maternal society,” he says.

“The original Trudeau opened the doors to Caribbean immigration,” says Riley, referring to former prime minister Pierre Trudeau. “People were welcomed and were glad to come here.”

They cleaned people’s homes, he said, “and if they were lucky enough to get a factory job” they did it to make it better for their kids, “like myself.”

Riley’s first memory as a child was at four, being held in his aunt’s arms, watching his mother get on a plane. “I’ve never been in therapy but I’m sure that’s affected me somehow. I see her waving still, to this day.”

Riley’s father was not in the picture at the time. His dad eventually settled in the U.S. and today they might speak by phone once a year, but the relationship is not close. His mom, now in her mid-70s, lives in Mississauga.

“My story wasn’t unique but it still was a tough way to do things,” he said. “She was courageous enough to do that, to come to a cold country, a very white country back then, where she knew no one, to give me a chance. And that’s why I’m never fearful of doing anything. People ask me if I’m ever afraid of going into court. No, I’m not. That’s nothing compared to what my mom did.”

The law  is actually his second career. Before there was Paul Riley the high-profile divorce lawyer, there was Paul Riley the television journalist.

But Pam, our server, is here to take our order before we can get to that part of the story. Riley orders a mushroom pizza but wants to start off with an order of shrimp. I ask for a customized chicken, mushroom and pineapple pizza but I take a hard pass on the curled crustaceans.

Riley is still reflecting on his early days in Canada. “There were only two things I ever wanted to be as a kid,” Riley says. “A television reporter and a lawyer. And I’ve done them both. And I think a lot of that had to do with my mother and the neighbourhood I grew up in.”

The first places he lived in were “the usual luxury spots” he says, tongue firmly in cheek, like Jane and Finch and Woolner Avenue in Toronto.

Eventually he and his mom would settle in the Capri Towers near the East Mall. It was government housing at the time.

Riley says he never once felt out of place in this neighbourhood, where an eclectic mix of people from all kinds of backgrounds could be found. “And across the street were middle class homes. But we all went to the same school, so I never felt I was disadvantaged.”

Riley says mixed neighbourhoods “are the most important thing” urban planners can make happen. “A kid sees where he can be. He doesn’t have to dream it; he can see it. He sees someone going to work in a suit and a tie so it’s not a farfetched fantasy. It just allowed a young kid to grow up with everyone else, so I never felt like my life should be limited.”

As the 6’ 5” Riley graduated from high school, Dalhousie University in Nova Scotia recruited him to play basketball. He got his undergraduate degree and then went back to Ontario to take journalism at Humber College.

But he couldn’t get a job in Toronto, where he really wanted to be. “So I thought, where else have I lived in this great country of ours? Halifax. They at least know my name there as a team captain,” from his years playing basketball.

He called up the CBC, CTV Atlantic (then known as ATV), and another TV news outlet whose name he can’t recall. “I cold called the executive producers. I said I’m a reporter in Toronto — and I was because I was writing freelance for NOW magazine at the time, while I was in journalism school (albeit mainly as a contributor of music and other arts reviews).

“I called CBC first and told them I wanted to move into TV. Said ‘I’m going to be in Halifax for Christmas, and I wonder if you can meet with me.’” He persisted and CBC’s hiring department eventually agreed.

“Once I had him, it was easy. Then I called ATV and said, listen, CBC is interviewing me at Christmas break, and the ATV producer said, well if he’s bringing you out to interview, we want to speak with you too.” The third producer? He absolutely insisted Riley come see him.

In the end, Riley was offered the job at CBC, the network where he most wanted to be, covering for a woman on maternity leave. He anchored on the weekend and did reporting during the week.

In the end, he graduated from Humber but didn’t even finish the first year, given that he had gotten employment so quickly since the school allowed one to exit early if the student had a job in their field. He landed a full-time TV gig within months at the CBC. Within 10 months, though, he had job offers back in Toronto because he had done stories that ended up on CNN and CBC-TV’s The National.

He returned to Toronto where he spent eight years with CBC Toronto, including anchoring the 11 p.m. news and sometimes the 6 p.m. news. He was also an occasional Newsworld anchor.

His career in journalism has been long in the rearview mirror, though, given that he’s been practicing law for 18 years. Riley graduated from Toronto’s’ Osgoode Hall to get his law degree, deciding to become the only other thing he dreamed about becoming as a kid – a lawyer, “running his own shop.”

Just as he was aggressive in pursuing his career in journalism, Riley is no shrinking violet in the courtroom, either, saying it’s been years since his firm lost a case — excluding a few incidents where clients didn’t listen to his advice. He also sees the skills from journalist to lawyer as transferable.

He explains his success this way. “For a corporate lawyer, it all comes down to the contract. For the criminal lawyer, it all comes down to the evidence. But for family law, it all comes down to a story. And I can tell a story better than any lawyer in this country. And you know why? Because I told over 1,000 of them at the CBC.”

Riley has anchored some significant family law cases, including a high-profile international child abduction case that was covered in The Globe and Mail in September.

The lawyer wasn’t planning on working in Kawartha Lakes, given he has offices in Ottawa and Toronto. However, he moved to the Little Britain area six years ago with his spouse, acupuncturist Lori Mitchell, and the peace and tranquility of the area has made him want to spend an increasing amount of time here. He opened a new office at 223 Kent St. W., in Lindsay, and Mitchell has taken some space at the back for her business.

In Ottawa and Toronto, Riley’s elevator pitch is: “We help professionals and high net worth individuals get out of bad relationships. And we fight to protect what’s rightfully theirs.” Kawartha Lakes doesn’t have quite the same number of such individuals.

“That’s why here this office is going to focus primarily on farm-related divorces. Farms may not necessarily mean high income but they have valuable assets,” says Riley. “There are unique issues in farm divorces involving equipment, livestock and crops.”

Riley finds that COVID has successfully accelerated his use of technology, allowing him to keep expanding virtual legal offices in places like Oakville and North York. “If I can stay here four days a week and not be anywhere else, that’s awesome,” he says.

Riley says he wants to be outstanding at whatever he does, from wherever he does it.

“When I came here (to Canada) I knew I wasn’t going to cause any problems or get into any trouble because my mother was gracious enough to give me a good life — and I will always be so grateful for that. I’ve owed it to her to always try and be exceptional at what I do because she took that risk.”

This year, for Christmas he’s starting a foundation in his mother’s name. It will make two $5,000 scholarships available to secondary students from disadvantaged neighbourhoods in Toronto.

As we wind up, I ask Riley what he loves most about living here.

“When I leave Toronto and I just get past Port Perry in my car, my heart rate goes down, my blood pressure goes down. I think it happens the moment I see the first cow or horse,” he laughs.

He says he loves Toronto and being close enough to go to a Raptors game or a theatre or a nice restaurant. “But then again there’s nice restaurants opening here now. I love the calm. We’re looking for a farm. Maybe just a handful of animals. I just love the country, man. It’s peaceful. Safe.”

He reflects on his “lucky” marriage with Mitchell and, given what he does every day, acknowledges that “Marriage is tough.”

When he was interviewed by Ottawa Life magazine the day before our lunch, he said the writer asked him, “Well, what about love?” in the context of what Riley does for a living.

“I said divorce isn’t a referendum on love. Lots of people get divorced and find love. Most people get divorced because they’re just not with the right person to begin with. That doesn’t mean that love doesn’t exist.”