Criminal defender by day, criminal imaginer by night, Robert Rotenberg understands, on an intimate and cutting-edge scale, the machinations of criminal masterminds.

There are three things that you need to know about criminal lawyer and bestselling author, Robert Rotenberg: First, he has never been afraid to grab the brass ring and live life to the fullest. Second, he has actualized and honed his successes in both the courtroom and on the page, always with a spirited sense of joie de vivre. And, third, Rotenberg is a humanitarian, caring as deeply about his clients, who he defends from a myriad of criminal charges, as he does for the protagonists in his six novels.

A dedicated proponent of putting actions to intent, when he was 14 years old, Rotenberg sent a short story to the gold standard of journalism, The New Yorker magazine, in hopes of getting it published. While that particular literary pitch was not successful, Rotenberg was, by no means, deterred. It would take a while, with many twists and turns along the way, but Rotenberg’s literary success — one that has been, from the start, adjacent to his criminal law practice — has translated into best-seller status. In fact, his recent novel, Downfall (February 2021, Simon & Schuster Canada), became an instant best-seller on The Globe and Mail’s and Toronto Star’s lists.

It has been an in-tandem career arc for Rotenberg, who, after graduating from the University of Toronto as an English Major, attended law school, where he ran the student criminal law legal department for a couple of years. He then went to the London (Ont.) School of Economics and, by the time he had finished up his education, Rotenberg had earned himself three degrees.

“I spent almost 10 years not being a lawyer,” Rotenberg says, with a laugh. “First, I got a job in Paris working on a magazine, called Passion. It was there that I learned how to write and edit. I, then, returned to Toronto and started my own magazine called TO Magazine; it was a young, hip contender to Toronto Life magazine. I worked 90 hours a week and made almost no money, but it was on this platform that I learned how to tell stories and really focus on the key points. After six years, I closed the magazine and moved on to a couple of other jobs. Then, all of a sudden, I was 37 years old with my first kid on the way, so I knew it was time to establish a real career. I rewrote my law exams, charged $3,000 to my VISA card and started my criminal law practice. There’s nothing like fear to motivate you.”

A genuine fascination with peoples’ stories is the juice that sparks Rotenberg’s interest; like a psychologist, one of his biggest passions is analyzing the hows and the whys of what caused or motivated a crime.

“I like to explore what my clients did to get to that moment where they did what they did,” Rotenberg says. “That’s what I find fascinating. In fact, that is the amazing thing about being a criminal lawyer. Within an hour of sitting down with me, people will tell me things they have never told anyone in their lives; sometimes that they have not even told themselves the real facts. I get them to talk about themselves: where they grew up, their parents, siblings, marriages, jobs. I want to know who they are, and I want to figure out what makes them tick because they are not going to be able to deal with whatever the consequences are until I get them to that point of acceptance. The main thing is to listen to people. I treat everyone with the same amount of respect, whether they are multimillionaires or one of my oldest clients. I act the same way with Crown attorneys and judges. I treat the process with respect. But, the real key is, I tell stories. And, while, originally, I resisted being a criminal lawyer — I’m almost incapable of filling out a form — if someone phoned me and said, ‘I’ve been charged with murder,’ I was in there like a dirty shirt.”

The telling-of-stories-through-novels began the first day that Rotenberg got home from his newly founded law practice. His first “book in the drawer” was good enough to secure him a respected literary agent in New York. But it was Old City Hall (2009) that became Rotenberg’s first published book, one that became a bestseller and was translated into nine languages.

Being a taxi driver in his earlier years equipped Rotenberg with an insider knowledge of the people, streets and neighbourhoods that make Toronto the prime setting for his novels.

“A lot of people ask me, ‘Why don’t you position your books in Chicago or New York, or some other big American city where you would reach a much wider audience?’ But the writing has to be real, you can’t fake it; I don’t live in those places,” Rotenberg says. “Also, I think Toronto has turned from being a boring city to a really fascinating one, a metropolis that is always in some kind of transition, and with that kind of change comes conflict, and with conflict comes drama. I think Toronto is a great place to write a book, and the sense of place in Toronto feels like who I am. Also, I have an audience that really appreciates that I write about Canada. I get so many emails from people saying, ‘I love your books because I know that neighbourhood; I used to live in Toronto.’ I got an email one time from someone in the United States, which said, ‘I live on the West Coast, and I’ve never been east of the Mississippi, but I feel like I’ve been to Toronto from just reading your books.’”

While Rotenberg states that he likes to keep his private life private, he is happy to share what the overall meaning of la dolce vita means to and for him.

“For me, the good life is about being productive, helping people and producing things. I have multiple careers [Rotenberg teaches writing at the Humber School for Writers and is also involved in screenwriting]; I work very hard,” the author says. “I’m very close with my brothers and my sisters-in-law, but, really, the most important thing in my life are my kids. At the end of the day, I want to be able to say that I’m doing the things I want to do. I always wanted to do jury trials. I always wanted to produce a magazine. I always wanted to write books, so I’m kind of amazed that I’ve been able to do it all.”