Shaun Rootenberg, romance scammer


To women in search of love, Shaun Rootenberg seemed like a catch. What they didn’t know: he’d spent decades stealing from just about anyone who crossed his path. Lonely women on dating sites were only his latest prey

| September 28, 2020

The first thing Victoria Smith noticed about “Shaun”—no last name, no picture—was his passion for adventure. It was hard to miss: his eHarmony profile mentioned it three times. She knew she could use some adventure in her life. Before her divorce, she had travelled widely, and even now, in her 40s, living alone in Toronto’s west end, her kids nearly grown, she tried to maintain that spirit. She’d recently visited Hawaii, exploring the lush, rubbery green of its rainforests and smelling the burnt ochre of its craters. But she wanted someone to share those experiences with. She clicked match. Soon, her phone pinged: he’d clicked match right back. They began exchanging emails.

Shaun told her his last name was Rothberg—which was close to his real surname, Rootenberg—and that he was a Toronto entrepreneur with a master’s degree. Like her, he was divorced and had two kids he adored. He liked hockey, though his first and deepest passion was soccer. He still dreamed about playing in the World Cup, which struck her as boyish and charming. He wanted to wake up every day, he said, trying to understand how he and his partner could ever have been apart. When she asked him about his travel philosophy, he volleyed back: “When are we leaving? My bags are packed.” He sent over some pictures. He was handsome, in his 40s, with a strong chin and dark, penetrating eyes. He had a deep, even tan and an understated sophistication—linen shirts, cashmere V-necks, designer sunglasses.

“I really am fortunate,” he wrote to her, “that I have a pretty great life. The only thing missing from it is someone to share both the good and bad times with.” Smith sent back a photo, showing her high cheekbones and long blonde hair, and told him that she liked collecting art and searching for new music online. They compared notes on what they considered the most important elements of a relationship. Chemistry and communication, they agreed. The ultimate dealbreaker? “Lying,” she wrote.

In August 2013, less than a month after their match, they met at a café. She walked in to find him more dapper than his photos suggested: his silver-flecked hair and square glasses gave him an air of seriousness. At five feet, eight inches, he was short, but had a strong, athletic physique. He was a gregarious and engaging storyteller, practically brimming with extraordinary, rollicking stories of his business career, of making millions off a deal and of champagne-soaked dinners with the billionaire Richard Branson. Smith was enamoured, and they met again and again. He introduced her to his two young sons. It struck her as strange that he drove an SUV and not the Aston Martin he often mentioned, but he explained that away: he sometimes drove his brother-in-law’s car because as a very private, very wealthy person, he liked to keep a low profile.

“In mid-September, a month and a half after they met, she handed over a bank draft for $160,000”


Smith had been a stay-at-home mom when her kids were young and came away from the divorce with her home, a condo that she rented out and around $600,000 in the bank. As their relationship progressed, Shaun often steered the conversation to his various business ventures, one of which was an idea called Trivia for Good. It was a gaming app, sort of like a forerunner to HQ, but with a charity angle, and it intrigued her. One day, he made his pitch: “Most of the company has been invested in, but there are still a few opportunities,” he said. She would get regular dividends and, later, if she wanted, she could sell her shares for a profit. Smith was excited to be involved in an endeavour that would make her money and do some good in the world. In mid-September, a month and a half after they met, she handed over a bank draft for $160,000.

Smith had suffered through a painful divorce and adjusted to the prospect of a life alone. It had been a long time since her future looked bright. Now, reluctantly, finally, she allowed herself to feel something like hope.

Lovers make the easiest marks. In the dating world, there is no consumer protection agency, no regulatory body or task force looking out for earnest seekers of love. That leaves the romantics—open-hearted, primed to trust, longing for intimacy—to fend for themselves. They’re led not by reason and logic but by the belief that somewhere out there is the person who’ll make their life shinier and easier, happier and complete.

We all want to believe we’re too smart to fall for a con. But our propensity to believe in something, or someone, rests far more on our state of mind than some predisposition. Someone going through a major life change—a lost job or a bad breakup—is more susceptible, because their equilibrium is off, but anyone anywhere can be had if the scammer is skilled enough.

In the U.S. in 2019, some 25,000 people reported being the victim of online romance scams, with losses estimated at more than $200 million (U.S.). In Canada in that same year, 760 Canadians lost $22.5 million to romance scammers, according to the Canadian Anti-Fraud Centre and the RCMP. In both countries, according to the FBI, romance scams now constitute the highest-loss form of consumer fraud.

Scammers lurk on all platforms—dating apps, social media, even online games. They construct elaborate excuses for why they can’t meet in person: they’re away on a foreign military posting, an oil rig or with an international aid organization. They offer even more elaborate reasons why they need money, and then take it and run. But Rootenberg wasn’t running your average romance scam—a cash grab performed from a safe distance. Not only did Rootenberg meet his victims in person, he worked his way into their hearts, homes and beds.

Around the same time Rootenberg and Smith’s relationship began, a woman named Kim Barker logged on to eHarmony. She was a 43-year-old doctor and newly single mother of three from Toronto who had just become medical officer of health at Algoma Public Health, in Sault Ste. Marie. Far from her adult kids and alone in a new city, she decided to try online dating. One profile caught her attention: “Shaun” said he worked in mergers and acquisitions in Toronto. There was no photo on his account, but looks were unimportant to her anyway. She was legally blind, a result of contracting malaria during a six-year stint in Tanzania working for UNICEF in her early 30s. But she could still discern the broad strokes of things, like the outlines of a man’s face if he was close enough to her. She could still read a computer screen, too. Under the heading “One thing you wish more people knew about you,” he’d written: “That I really do care.” She’d devoted her life to helping others, and that line resonated. She clicked match. Soon, they were speaking by phone at least twice a day. The glamorous life he described fascinated her. His latest venture, he told her, was a platform he was launching with Richard Branson, and he was flying to London weekly for visits. “It will transform media and advertising,” he said.

“I have to be honest with you, Shaun,” she said. “I feel like you’re totally out of my league. I just don’t swing in those kinds of circles.”


“That’s what I like about you,” he replied. “You’re down to earth.”

"Lovers make the easiest marks": Profile of a romance scammer
Rootenberg with Barker on a work trip to Israel in February 2014, three months after she’d hired him as the interim CFO of Algoma Public Health

Barker knew she needed to learn to trust people. It had never been her strength, and years of breakups had chipped away at what little trust she had left. It helped that she was drawn to him. He had a mysteriousness that both unnerved and enticed her. In September 2013, as Shaun’s relationship with Smith was growing more serious, he drove to Sault Ste. Marie. Barker was surprised when he arrived in an SUV and not the Aston Martin he had mentioned. As a person of immense wealth, he explained, he was constantly concerned with people tracking him, so he borrowed his brother-in-law’s car. “When you make as much money as I do,” he said, “you like to stay private.”

Their relationship progressed quickly. They spoke on the phone multiple times a day and met in Toronto on weekends. He told her all about Trivia for Good, and how the proceeds would go to helping people in need. He urged her to invest, but she declined. “This is what happened with my wife,” he said. “She didn’t want to be involved with me and what I believed in. She didn’t trust me.” Barker’s stomach tightened. She might lose the first man she’d grown to care for in years, and who wanted her in return. She wrote him a cheque for $100,000 and made it out to “Shaun Rothberg.”

When the bank called to verify the transaction, they told her she’d made a spelling mistake. Shaun’s last name was Rootenberg, they said. When she googled that name and discovered that he had a criminal record, she felt betrayed. She confronted him and he mounted an impassioned defence. He had been charged with fraud, he said, but it was all a misunderstanding. He told her how he’d sued RBC and won (a lie), sued the Toronto Star (a lie) and was in the middle of suing the courts system for a terrible miscarriage of justice (the application was dismissed; so was the appeal). He showed her court documents as proof. He’d been mistreated by the banks, the media and the courts, and all he wanted was a chance to start over. He just needed someone to believe in him. She decided that someone could be her.

In late September, they travelled together to Big White resort, near Kelowna. Barker was a frequent flyer, and she assumed he was, too: Rootenberg had called her from the Maple Leaf Lounge before—or so he said—so on the day of the flight, she went there expecting to find him. He wasn’t there. When she reached him on the phone, he explained that he didn’t like the risk of missing the flight so he always sat by the gate. Once she got there, she found him surrounded by luxury magazines, poring over pages filled with cars, yachts and vacation spots. It was bizarre, she thought, that he would buy so many magazines that were available for free in the lounge. When she said as much, he turned it around on her. He felt irritated by her interrogation and reminded her of the importance of trust in their relationship. They smoothed things over, but she couldn’t shake the feeling that it all seemed a bit strange.

Shaun Rootenberg was born into a life of opportunity. His parents, Abraham and Vivienne Rootenberg, were immigrants from South Africa who moved to Toronto to become real estate agents and raise their four kids. Shaun, their youngest, attended the private United Synagogue Day School and then Crescent School in North Toronto. He was a strong athlete, a good math student and generally popular, but he was most gifted at self-mythologizing. He discovered early on that a well-placed lie could make him sound and feel more important than he was. One friend remembers Rootenberg as a chronic exaggerator. He’d claim to have scored high on nearly every test yet never finish the year atop the class, and he’d tell unbelievable stories of the many attractive girls he’d hooked up with during the summers.

After high school, Rootenberg studied at the University of Western Ontario. He tried out for varsity soccer but didn’t make the team, so he told friends he’d instead been recruited to play for the elite Maccabi Canada rep soccer team in Israel. According to one source, Rootenberg went so far as to buy the uniform and travel to Israel during the tournament.

By that time, Shaun’s siblings were establishing their careers: his brother Jonathan would become a renowned forensic psychiatrist, his sister Terry an occupational therapist and Michael a car salesman. Sources I spoke to said that while Rootenberg had a brilliant mind, he was a terrible speller and had trouble constructing a coherent paragraph. They suspected he had an undiagnosed learning disability.

After university, a friend offered him a job at a collections agency, and, left with no better options, he accepted. Hounding borrowers for repayment was hardly glamorous, but he was good at it. On the phone, he could be assertive and bend the truth as far as he needed to get the borrower to pay up. “I’m going to sue you,” he’d say in a flat, icy tone. “If you don’t pay, I’m going to take you to court.” After he was promoted to manager, he lied to his supervisors that he kept the Jewish Sabbath and he needed to leave early on Fridays and could never work Saturdays.

Around the same time, Rootenberg met a physiotherapist named Lana Rotstein. She had chestnut-brown hair, had also attended Western, and they had mutual friends. At their wedding, in the late ’90s, Rootenberg’s new mother-in-law lauded his charm and intellect in her speech. “We’re thrilled our daughter is marrying someone so successful,” she said. “Though we still don’t really know what it is you do.” The crowd laughed along.


The Rootenbergs soon welcomed two boys, the first of whom was born with autism. Rootenberg’s in-laws loaned them money toward a down payment on a home in Lawrence Park, according to a source. Rootenberg’s job didn’t afford him the lifestyle of his neighbours, but that didn’t stop him from spending like it did. He bought himself a Porsche. When Lana wanted to improve her cooking, he flew her to Italy for classes.

“He crowed about the multimillion-dollar deal he brokered that got the attention of Richard Branson, who invited him to his castle in Scotland”


Rootenberg found collections work gruelling, so he created a fake resumé and, with a colleague, formed a management consultancy. He talked his way into a business strategy role at Dell. From there, he moved on to Compaq Financial as a salesperson in the business development division. The ruse lasted until his bosses realized he didn’t have the skills he claimed—but before they could fire him, he’d talked his way into another business role, as executive vice-president of the venture capital group SKG Interactive, which was also short-lived. The pressure began to mount—his mortgage was large, and he had other debt, too—so he returned to the collections racket. For some, that would have been fine: it was steady and honest in theory. But he had bigger aspirations.

Rootenberg created a corporation called Jonevan Investments and joined Magna Golf Club, the private club opened by auto parts and horse racing magnate Frank Stronach. On the course, he went to work, using the truth as a base then layering on lies as needed. He would say that he’d attended Western University’s Ivey Business School, played varsity soccer and earned an MBA from Georgetown University. After that, he’d moved back to Canada, married the heiress to a diamond fortune (Rotstein’s father owned a jewellery store) and became a successful investor. He crowed about the multimillion-dollar deal he brokered that got the attention of Richard Branson, who invited him to his castle in Scotland. Rootenberg said he advised the city’s power players on their investments. He offered returns big enough to entice, but not so big as to invite suspicion. It worked. A doctor invested $20,000, and when he got a 20 per cent return, invested another $75,000, which disappeared. A senior lawyer at a Bay Street firm bought in; so did an NHL player. Of course, their money was never invested—it just went into his personal slush fund.

At the time, Ponzi schemes weren’t a mainstream phenomenon—it would be eight years before the New York financier Bernie Madoff’s fake empire would fall. The key to a Ponzi scheme is trust: the mark needs to believe that the person they’re handing money to has the pedigree and the genius to beat the market. Rootenberg bore the hallmarks of success—the expensive car, the North Toronto house—and he talked the talk. For many, that would be enough.

While his Ponzi scheme was taking off, Rootenberg continued to work at the collections agency, where he was seemingly soaring: he was blowing past his monthly targets and earning thousands of dollars in commissions. He was the star of the company, until his bosses received calls from strangers asking why money had been withdrawn from their accounts. The company discovered that the account numbers Rootenberg had written on deposit slips were real but didn’t belong to the debtors he purported to collect from. He was fired but managed to talk his way into another agency. According to a former co-worker, within a week, regulatory officers walked in, pulled him from his cubicle, tore up his licence and banned him from the industry.

Rootenberg kept up appearances—he took his wife and kids on expensive vacations—but fault lines were starting to show. The couple took out multiple mortgages on their home, and, according to one source, they were forced to sell. When the couple finally divorced, Lana’s credit was so decimated that she had trouble buying a car. He forged his mother-in-law’s signature to secure a mortgage on his in-laws’ North York home, and walked out of the bank with $320,000. When Rootenberg’s father-in-law’s jewellery store was robbed at gunpoint, one friend couldn’t help but wonder if Rootenberg was involved. He was never charged—no one was—but the speculation alone was a sign of how fractured his relationships had become. Of course, that hardly mattered. Rootenberg knew he was charismatic enough to start over with new friends, who would soon become marks, and the sick cycle would begin again.

In 2006, Rootenberg found his next victim, an executive from Montreal. (She requested anonymity so her name wouldn’t be linked to Rootenberg’s online.) After dating for a while, and after she’d loaned him more than $200,000, they bought a home next door to where his brother Jonathan and sister-in-law Karyn lived, a five-bedroom house in Lawrence Park. She thought she’d met the father of her future children. He thought he’d discovered a gold mine.

By this point, he’d perfected his sales pitch. When she introduced him to friends, he bombarded them with hyperbole and rapid-fire sentences. “He talks too fast, and it sounds great, and it’s convincing,” one executive says. “He’ll lie straight to your face, and even when he gets caught with his hand in the cookie jar, he’ll deny it.” A tech entrepreneur named Guy Vadish gave him $250,000. A Florida financier named Jeremy Schwimmer who runs an investment fund wired him $400,000 for a deal supposedly related to the former retail chain Music World. He pretended he was their friend, generously covering meals and drinks. Of course, it was usually with their own money. “There’s a difference between thieves and fraudsters,” one former friend says. “Both are stealing from you, but one of them’s doing it right in front of you.”

When it came time for the Lawrence Park house to close, Rootenberg couldn’t come through with his portion of the funds, and the relationship with his girlfriend quickly deteriorated. In the months that followed, she came to understand the extent to which she’d been conned: he’d used her bank account to move money and her network to find new marks. “He doesn’t think the way people normally think,” she says. “We simply can’t imagine someone so close to us being that disingenuous until the evidence is overwhelming.”


When Schwimmer and Vadish inquired about their investments, Rootenberg told them there had been a mix-up and the deal had gone ahead without them. When they asked for repayment, he doled out excuses. When they became irate, Rootenberg wrote Jonevan Investments a personal cheque for $1.75 million (U.S.) and had his lawyer deposit it. He printed out the bank balance and showed everyone the slip, which calmed them down. Two days later, the cheque bounced. Vadish called the police, and Rootenberg was arrested, but his sister, Terry, and his brother Jonathan posted bail.

Beaver Creek Institution
Rootenberg served three years and six months at Beaver Creek in Gravenhurst, on the same unit as three other well-known white-collar criminals
Joseph Grmovsek, infamous insider trader; Garth Drabinsky, former theatre impresario; and Myron Gottlieb, Drabinsky’s former money man
His pen pals, from left: Joseph Grmovsek, infamous insider trader; Garth Drabinsky, former theatre impresario; and Myron Gottlieb, Drabinsky’s former money man

Rootenberg continued to try to outsmart the law, consequences be damned. Later that summer, he walked into a bank at Bayview and York Mills and introduced himself as Jonathan, handed over his brother’s passport and a notice of assessment on his property and said he wanted to apply for a $650,000 mortgage on his home and a $550,000 line of credit secured by the property. He forged Jonathan’s signature and walked away with a $100,000 loan and a Visa in his brother’s name. When the bank approved the $1.2 million in funds, Shaun went on a spending spree. When Jonathan and Karyn found out, they called the police. Shaun learned the cops were after him and hopped into his car and disappeared. Police issued a Canada-wide warrant for his arrest and traced him to Vancouver, where he’d been using Jonathan’s ID and credit card. Yet the police couldn’t pinpoint his exact location—they suspected he was living in his car. On March 12, 2009, after an article featuring his mug shot ran in the Toronto Star, he walked into a North York police station and surrendered. He approached the cop on duty and said, “I just want to deal with it.” He pleaded guilty to two counts of fraud totalling $2.2 million—against his friends, his girlfriend, his brother and his sister-in-law—just a tiny portion of the scams he’d pulled. A former best friend, Jeff Greenberg, saw the news about the sentencing. To the Star, he called Rootenberg’s scamming “pathological” and delivered an eerily prescient quote: “He’s probably on dating sites, too. He’s probably trying to find a girl.”

“His mug shot had been in the paper, and the word was out on Bay Street. Rootenberg needed a new scheme where he could put his skills of deception to use. And he found it in online dating”


At Beaver Creek Institution in Gravenhurst, Rootenberg typically slept for just four hours a night. He’d never needed much sleep, even in childhood. Around 2 a.m., he’d climb down from his bunk and watch TV until the lights flicked on at 6 a.m. His cellmate was Joseph Grmovsek, a Canadian lawyer convicted of insider trading in 2009, and he shared a unit with Garth Drabinsky, the former theatre impresario who was convicted of fraud in 2009 for a scheme that cost investors an estimated $500 million. “Garth and Shaun avoided each other. The joke among the other cons,” Grmovsek says, “is that they each knew the other was full of shit—because they were.” Rootenberg made friends with Drabinsky’s associate, Myron Gottlieb, who’d also been convicted of fraud, and he would later assist Rootenberg with setting up Trivia for Good. In prison, they ordered special kosher meals, even though Rootenberg didn’t keep kosher at home.

When Rootenberg was released in 2012, he tried to pick up where he’d left off. At first, he was successful. He persuaded a new business partner to lease an opulent condo near Eglinton and Bathurst under his company name. After a few months, Rootenberg stopped paying rent and then brought a suit against the landlord, claiming water damage. He bought another Porsche, which he would drive to his rec soccer games, regaling his teammates with outlandish stories of business victories over post-game beers. He’d call up old acquaintances to ask if they wanted to join him for a golf game. When they’d say they couldn’t, he’d impersonate them on the course, blowing puffs of smoke from cigars he’d charged to their account. He was right back into his old life of luxury, but he was smart enough to know it couldn’t last. His mug shot had been in the paper, and the word was out on Bay Street. His Ponzi days were over. Ever the problem solver, Rootenberg needed a new scheme where he could put his skills of deception to use. And he found it in online dating.

It was eight months after Rootenberg’s release from prison that Victoria Smith, the divorced mom who loved to travel, fell for him. She had no idea that her boyfriend had spent three years in prison and was a career con artist. And within months of meeting him, she had handed over $160,000. Sensing an even bigger windfall, Rootenberg asked if she wanted to invest the rest of her savings. Smith didn’t know much about finance, but she felt uneasy about the stock market’s volatility and wanted something steadier, something like real estate. Rootenberg said that made sense. He said he’d done deals with a company that provided second mortgages. If she invested the rest with him, she’d earn generous dividends. If she wanted, he said casually, he could handle the investment through his company, B-G Enterprises. The corporation was named after his big gonads, he told her. They laughed. (It was in fact Gottlieb’s company and named after Gottlieb’s wife, Bonnie.) In October 2013, Smith gave him a bank draft for $435,000, the rest of her savings. He went to a car dealership and walked out twirling the keys to a shiny black BMW worth $50,000.

At the time, Smith had no reason to think anything was amiss: what seemed like legitimate dividend cheques arrived regularly, and their relationship seemed better than ever. Rootenberg paid for three vacations to the Bahamas, once bringing along his sons and Smith’s daughter. From the beginning, Smith had asked for documentation of her transactions. What if something happened to him, she wanted to know? “Of course,” Rootenberg said. He emailed her trust deeds with the subject line: “In case this plane goes down.” But there was no investment, and the deeds were fake.

While Rootenberg was dating Smith, he would visit his other girlfriend, Kim Barker, the medical officer of health in Sault Ste. Marie. Rootenberg had already convinced Barker to invest $100,000, but he was looking for another payday. Barker had explained that she was having trouble finding a qualified candidate to serve as chief financial officer to oversee Algoma Public Health’s $23-million annual expense budget and $25 million worth of assets. Shaun offered to introduce Barker to an executive recruiter named Ron Hulse, who would later become the president and COO of Trivia for Good. Barker accepted. Hulse’s suggestion? His old friend Shaun. Hulse knew about Rootenberg’s criminal past, but Rootenberg had told him he was trying to change, and Hulse believed in second chances. And so, Barker hired her boyfriend as interim chief financial officer, with a salary of $205,400, without disclosing their relationship to the board.

For Barker, warning signs abounded. But she loved him and wanted the relationship to work. Besides, he explained away his odd behaviour so well. When he’d pay for everything in cash, even big-ticket items, he said it was a matter of privacy. She agreed to open a joint bank account in her name because he said his criminal record prevented him from doing so. She also applied for a MasterCard and added him to the account, which meant the bank didn’t complete a background check on Rootenberg. When he started ringing up the account, she was unaware: he’d signed them up for paperless billing, and only he knew the password to the online account.

Eventually, Rootenberg struggled to manage both relationships. To cover his tracks in case they ever met, he told Smith that Barker was his boss, which she was, but told Barker nothing about Smith. At the same time, he told friends that he was in open relationships with both women.

For a year or so, his double life worked. Then, in November 2014, he and his ex-wife hosted a joint bar mitzvah for his sons at a giant hall in North York. Rootenberg invited both of his girlfriends and seated them at different tables, mixed in with family, colleagues and friends from prison. Inevitably, Smith and Barker crossed paths. Smith introduced herself, but Barker didn’t know who she was. Smith was surprised. She assumed her name would have come up in conversation between her boyfriend and his boss.


Days later, Rootenberg’s scheme was spoiled by the unlikeliest culprit: dessert. Smith took some leftover dessert home, and her son’s friend took some to his girlfriend’s house. There, her father asked where the sweets had come from. When he said a bar mitzvah thrown by a guy named Shaun Rothberg, he looked startled. That name sounded familiar, he said. He remembered reading about a serial fraudster who’d used it and was convicted years earlier. He found a photo online and the young man recognized it as the man he’d seen at Smith’s house. Smith’s son’s friend told her what he’d learned: that her boyfriend’s last name wasn’t Rothberg, but Rootenberg. He’d served time in jail for fraud. He was a career con man, a professional liar. Smith’s world began to quake. The warning signs she’d ignored wailed like sirens in her head. Why had she never seen his home? He said it was because he lived with an ex. Why did he pay for everything in cash? The man she loved was an imposter. And he had her life savings.

When Rootenberg walked into her house hours later, she confronted him. Rootenberg apologized and spun his sob story: he admitted to lying and to the crimes he’d committed but assured her he’d changed. “That’s not who I am anymore,” he said. That’s why he’d given her a different name and why he’d been vague about his past. A surge of panic rose in her. Where was her money? She asked for it back. But he convinced her it would all work out if she just gave him her trust and some time. She decided not to call the police. If she stayed in the relationship, she thought, she might get her $600,000 back.

“When Smith finally realized that her life savings were gone, she was devastated. Her days became a haze of panic attacks and tears”


Her decision didn’t last. It was too hard to be with someone she didn’t trust. After one last trip together, to New York, she broke up with him. Still, they stayed in touch, exchanging texts and talking on the phone. Where she had before asked politely for her money, now she insisted. He’d respond by toying with her, proposing a date to meet to sign the necessary documents and then rescheduling again and again.

When Smith finally realized, deep down, that her life savings were gone, she was devastated. Her days became a haze of panic attacks and tears. She became deeply depressed and stopped seeing most of her friends, swallowed by shame and uncertain how she’d tell anyone what had happened. She couldn’t keep food down. She attempted suicide. She went to rehab. When she texted Rootenberg to tell him she was thinking about trying to kill herself again, he texted back: “Please don’t, and I wish you would get together with me.” Smith moved out of her home and in with a friend. Her family kept her close, calling every few hours to make sure she was still alive.

The sick carousel of broken promises Rootenberg spun for Smith lasted two years. Finally, she called the police and reached a detective named Paul Mackrell, a cop who’d made his career going after fraudsters. He’s gruff, with a buzz cut and leathery skin. Not every reported fraud turns into a case, but something in the fragility of Smith’s voice stuck with him. The police took statements from her and met with Rootenberg’s former business partners, who told him they’d been scammed too. Fraud cases can be difficult to prove. In his decade in the unit, Mackrell had spent months on other cases poring over stacks of bank documents looking for the tiniest discrepancies. Smith’s case was straightforward by comparison, and he thought it would hold up in court. He was right. Rootenberg was charged with fraud and money laundering, and in June of 2017, he turned himself in again. “I just want to get this dealt with,” he said haughtily as he was handcuffed. Mackrell was taken aback. “I think fraudsters believe their own bullshit,” he says. “It’s easier to live with yourself that way.”

In January 2015, three months after Smith finally saw through Rootenberg’s lies, Barker had her own reckoning. Jonathan Rootenberg, the forensic psychiatrist, came to examine a patient in Sault Ste. Marie, where his brother was still known as Shaun Rothberg. When Barker invited Jonathan to use one of the clinics at the Algoma Public Health offices, the receptionist there googled the psychiatrist’s name and Shaun’s mug shot came up. She called her boss. The town exploded.

The mayor called Barker, incensed. Barker was mortified. She resigned in disgrace and took a job in Iqaluit as the territory’s health officer. But despite the major transgression, she stayed with Rootenberg. She still loved him, still believed he’d been mistreated by the courts and was still fearful she wouldn’t find another partner to spend her life with. They vacationed together in the Bahamas. By then, they’d been together for almost three years. “I’m so impressed that you maintain such a faithful relationship to me when you could be with so many other women and we’re so far apart,” she told him one night on the phone. “That’s just who I am,” he replied.

Yet as evidence of Rootenberg’s little lies piled up, Barker began to wonder if he was worth all the drama that seemed to follow him. Then, CIBC called to tell her that he’d rung up $28,000 in overdraft on their shared accounts. Barker was stunned. She called Ron Hulse—they had kept in touch—to discuss the situation. Hulse offered his sympathy. It seemed, he said, that Rootenberg was conning again. “I feel so sorry for Victoria,” he added, calling Smith by her first name. Barker replied, “Who?” “Oh,” Hulse replied. “I thought you all knew about each other. He told me the two of you were in an open relationship.” Barker flinched. An open relationship? What was he talking about? Hulse told her about Smith.

Barker called Rootenberg and asked him to meet her for dinner. Outside the Keg at Yonge and Eglinton, she called him and said: “Did you book a table for three?” Rootenberg was speechless for what seemed to her like the first time ever. “I guess I shouldn’t come,” he said. That, she told him, was up to him. It was Christmastime in 2016, and she sat alone in a leather booth. When he finally slid onto the opposite bench, his face expressionless, she knew it was over. “How could you do this to me?” she asked him. “Why did you think I deserved this?”

“My intent was never to hurt you,” he told her. “I loved you more than I’ve ever loved any woman in my life.” She started to cry. He stood up and walked away. When Barker stopped crying, she looked up. He’d left her with the bill.


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In July of 2019, Rootenberg was convicted of defrauding Smith, but it’s unlikely she’ll ever be made whole. After Rootenberg was found guilty, he trained his prodigious talent for bluster and subterfuge on a different kind of target: the courts. Representing himself, he filed a mistrial application, arguing that the judge was biased, which was dismissed. Then he argued for a stay of his conviction on the grounds that the number of times he was strip-searched in prison was so degrading as to be unconstitutional, an action that was also dismissed. The cascading actions delayed the sentencing, costing Rootenberg nothing but time, which was exactly what he wanted.

In February 2020, Rootenberg sat in a Toronto courtroom for his sentencing hearing. He appeared calm, dressed in a zipped grey sweater, occasionally pausing to check the time on his Apple Watch, like he had somewhere better to be. He leaned back casually as he answered the prosecutor’s questions. Family members from whom he’d swindled hundreds of thousands of dollars each provided a letter of support. As Rootenberg sat listening to the Crown attorney read out Smith’s victim impact statement, in which she outlines her suicide attempt, her panic attacks, the funhouse nightmare of uncertain reality in which she now lives, his face betrayed nothing. It wasn’t a bluff: according to many sources I spoke to, Rootenberg is resolute in his belief that he’s done nothing wrong, that bad investments sometimes go sour and that he is the real victim in all this (he intends to appeal the conviction). “I don’t even think he knows what’s real anymore,” says Greenberg, his former best friend.

For Smith, once an open-hearted free spirit, the world is now a more sinister place. Barker says she’ll never date again. “How could I?” she says softly. The emotional ramifications feel endless, and the financial repercussions keep crashing over her life like waves. Barker recently received a letter from CIBC saying her money was no longer welcome at their bank. In that regard, she joins a long list of victims. A former colleague of Shaun’s has had his credit decimated so badly that even his 90-year-old mother was told to take her banking business elsewhere. A friend who invested $250,000 that he never got back nearly lost his house. RBC came for Rootenberg’s brother’s house, too, before the family reached a confidential settlement with the bank. Rootenberg, meanwhile, has found a way to make even a pandemic work for him. After the courts closed because of Covid-19, his hearing was postponed, then postponed again. In the meantime, he’s been living at his sister Terry’s house in Thornhill.

One sweltering July day, a month after he’d been granted yet another court delay, I pulled up in front of the three-storey brick house, on a quiet cul-de-sac. I knocked on the door. Inside, a dog barked maniacally, but no one answered. Then the garage door lifted and an SUV backed out. Rootenberg was alone behind the wheel, white AirPods in his ears. A cool puff of air hit my face as he lowered his window. I asked if he was Shaun. He said evenly that he was, peering out at me, his eyes beady in the sun. I explained why I was there and asked if he’d care speak to me for the story I was writing about him. His demeanour turned cold and his sentences clipped. “Why would I talk to you? The press is biased,” he said. “All that ever gets printed about me is lies.” Then he rolled up the window and drove off, slipping around the corner and out of sight.

This story appears in the October 2020 issue of Toronto Life magazine. To subscribe, for just $29.95 a year, click here.


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