Design to make Visual

Meet the most charming fraudster in GTA real estate

When his inbox pinged early one summer day in 2020, Dundas Kwok adjusted his glasses, leaned forward and clicked. The message was from a real estate consultant named Courtney Wallis Simpson, and she had two exclusive, yet-to-be-advertised listings she thought he might be interested in. Kwok wasn’t familiar with the sender’s name, but he was always on the lookout for potential investments. The 67-year-old had been in real estate development for almost two decades, working as the director of marketing and sales for King Square Shopping Centre in Markham before founding a brokerage and then moving into development. His curiosity piqued, Kwok wrote Simpson back, asking for more information.

The first site, she explained, was a vacant lot in Barrie zoned for townhouses, with a sticker price of $3 million. The second, a $2.5-million listing in Stouffville, Ontario, on more than four acres, was an open plot with potential for land-banking. That meant Kwok could acquire the property and then develop it down the line when it would be most profitable.

The more he learned, the keener Kwok became about the opportunities Simpson was pitching. The real estate market, which had stalled in the early months of Covid, was bouncing back. Mortgage rates hadn’t been this low in three years. And as work-from-home became the new normal, cramped downtown home­owners were turning to bedroom communities like Barrie and Stouffville for more square footage and outdoor space. There was money to be made, and Kwok wanted to get in on it.

Several investors, including Dundas Kwok, put down large deposits on this $3-million plot of land in Barrie between 2020 and 2021. Photo by Lucy Lu

Simpson was working with a brokerage called Wynn Realty Corporation, owned by her husband, Wayne. She explained to Kwok that she was helping Wayne with the ­business but that she was really the one who handled everything. She presented Kwok with detailed packages about the parcels of land, including specs, site plans and environmental reports, and diligently answered his questions. Deals involving vacant land are complex, with many factors to consider, including zoning laws and soil remediation. Over the course of their exchanges, Simpson proved to be knowledgeable and professional, putting him at ease.

Kwok visited the sites in person several times between the summers of 2020 and 2021, sometimes meeting up with Simpson. She greeted him cheerfully, excited about bringing him into what she assured him was a great deal. Petite, with a mane of bottle-blonde hair, the 55-year-old had the frenetic vibe of a hamster on a wheel, but he could tell from her pitch that she had the instincts of a shark. Kwok foresaw some potential problems with the properties, but Simpson reminded him that he could change his mind—a common occurrence with complicated deals of this nature and one that carried no penalty. She forwarded him a mutual release that would allow him to recover his deposit. Convinced, he sent Simpson two deposits by certified cheque totalling $250,000.

Kwok was enthused about the projects, but he wasn’t operating alone—and after further conversations with his investors and partners about the complexities of the offers, he eventually decided to pull out. He contacted Simpson in June of 2021 to cancel the deal, sending her the mutual release. Simpson wrote back, telling him not to worry about the paperwork and confirming that the deal was indeed off. When he followed up with her again a few days later, she said she was in the midst of moving offices and would send him a cheque when she had more time, promising to get in touch soon.

Kwok was nervous, a feeling that only grew as a few more days went by without word from Simpson. After 20 years in the business, he was accustomed to delays and comfortable with a certain amount of risk, but this kind of thing had never happened to him. His anxiety turning to frustration, he called Simpson to demand that she return his deposits—only to discover that her number was no longer in service.

Related: The real estate mogul who left 200 home buyers in his lurch

Shocked, Kwok did the first thing he could think of: he reported Simpson and Wynn Realty Corporation to the Real Estate Council of Ontario, the body charged with regulating real estate professionals. “At that point,” he says, “I thought maybe she had stolen the trust money and run away to South America.” In the best case scenario, RECO would help catch her and get his investments back.

It would take a year, but part of Kwok’s wish did come true. On July 13, 2022, Peel police arrested Courtney Wallis Simpson and her husband, Kenneth Wayne Simpson, and formally charged them with fraud, forgery, theft and possession of the proceeds of a crime. Kwok learned that this wasn’t a one-time error in judgment, either: there were at least 16 other victims. Not only was his money gone, but Kwok would soon find out that Simpson hadn’t even been authorized to sell the properties he thought he was buying. The couple is now facing more than 100 charges—84 for her, 30 for him—for collecting millions in ­deposits through illegitimate transactions.

Kwok and the other would-be buyers also learned that they were part of a much larger club. This wasn’t the first time Simpson had been arrested and charged. She had been defrauding eager real estate investors on and off for two decades, subsisting on grift and a deluded self-image—one in which she’s a scrappy underdog, always on the verge of finally getting what she deserves. To believe Simpson, she’s alternately a victim of extensive conspiracies; a misunderstood martyr; or an innocent mother, wife and legitimate businesswoman trying her best to have it all. In truth, in a real estate market as hot as the GTA’s, she was a predator who saw marks everywhere she looked, even among friends. Dundas Kwok was just unlucky enough to cross her path.
It shouldn’t have been so easy to pull off. In Ontario, there are roughly 100,000 real estate agents and brokers spread over 38 real estate boards. Those agents and brokers make about 250,000 transactions each year—which, between 2012 and 2021, amounted to $1.2 trillion in residential resales alone. In order to do business, agents have to register with RECO, which was created by the Mike Harris government in 1997 to administer clear rules for the real estate profession and protect consumers. Agents also have to enroll in a real estate education program that includes five courses, four exams and two simulations. Then, within two years of being in business, they must complete an additional three courses.

If agents wish to go on to become brokers (so they can employ agents), they must pass the broker qualifying exam, and both agents and brokers are also required to complete mandatory continuing education classes every two years in order to renew their registrations. The time commitment alone ought to be enough to weed out most real estate fraudsters.

Outside the industry, opportunities abound for scammers looking for quick paydays through real estate fraud. For example, title fraud—the illegal practice of impersonating unsuspecting property owners and selling their houses out from under them—is often perpetrated by people simply pretending to be agents and brokers.

Simpson’s property schemes amounted to almost $15 million in losses, included more than 140 victims and resulted in 23 charges against her

Simpson is remarkable in part because, having earned her agent’s licence in 1990, she knew the industry from the inside. And instead of focusing solely on non-experts, she often targeted her own people. She went after brokers and ­developers—fellow professionals who were taken in by her natural charm and knowledge of their shared industry.

Simpson would have been aware that RECO was stretched too thin to properly enforce the rules that might have tripped her up. RECO staff, for instance, are expected to regularly visit brokerages and review their accounts, financial documents and advertising materials. But, according to a report released by the office of the auditor general of Ontario in 2022, more than a quarter of all brokerages in the province have never been inspected. In Simpson’s case, following a bail hearing for her in 2005, her father gave a statement to the Toronto Star saying that her brokerage had been inspected by RECO three times the previous year and had passed all three audits. It’s unclear whether that claim is true; when contacted for this story, RECO refused to provide details regarding the contents of its inspection records.

There is likewise no system in place to assess what to do if an applicant has a criminal record. That’s left to the discretion of individual registration officers, who have the power to decide whether the applicant poses a risk to the public or the profession. As of 2022, 1,700 real estate professionals in Ontario had disclosed criminal charges or convictions on their applications—some involved fraud, including the use of fraudulent cheques and stealing financial data from credit and debit card users. Although a criminal background check is required by RECO during the application process, there’s no such requirement when it comes time to renew a registration. As a result, there is no way for RECO to track which salespeople and brokers have committed crimes since their initial registration unless they choose to self-disclose.
Even in grade school, Simpson showed signs of the woman to come: she was a lively and astute little show-off willing to transgress boundaries. Wayne Lambert is an 80-year-old Stouffville resident who has known Simpson and her family since she was young. He recalls an afternoon when he babysat Simpson and several of her friends after school. Simpson split away from the group, and Lambert found her in his bedroom, rifling through one of the closets. “The problem with her is that she never thinks she’s doing anything wrong,” he says.

Looking back, there was also early evidence of Simpson’s entrepreneurial instincts: at the age of 12, she set up a babysitting service and hired a bunch of local girls to work under her, taking a 10 per cent commission from their earnings. In high school, when she was profiled for a “girl next door” series in the Stouffville Sun-Tribune, she told the reporter that her future plans included having nine children, moving to Toronto to live in Rosedale, and becoming a surgeon, a part-time hockey scout and a Conservative politician—though not the prime minister because she didn’t like the official residence on Sussex Drive.

Wallis-Simpson at 6 years old

And as a teenager

When she was 16, Simpson started dating a neighbourhood boy. They eventually married and, in 1988, when Simpson was 23, had a daughter. Soon, she was juggling motherhood and work. Between 1990 and 1992, she got her realtor’s and broker’s licences and set up her own brokerage. The industry was a natural fit for a born hustler. Starting out as a sales­person with REMAX, she was determined to become the top agent in the GTA as quickly as possible. Simpson loved the potential in real estate, particularly the rush of bringing empty spaces to life. “When you secure a piece of raw land and you turn that into a community with houses and families and swing sets, it’s miraculous,” Simpson told me. “It’s like giving birth to a child.”

After a few years, her marriage fell apart, and real estate became a lifeline—and the framework for a meet-cute. In 1993, Simpson tripped at the site of pre-development townhouses she was selling, and a tall, handsome stranger rushed over to help her up. Twenty years her senior, Wayne Simpson already had three children of his own. The couple fell hard, tying the knot three years later and having a son three years after that. When the bride saw the marriage licence, it struck her that she now shared a name with Wallis Simpson, the American divorcee who had inspired Edward VIII to abdicate the British throne, a woman famous for saying that you could never be too thin—or too rich.
As a broker, Simpson made big promises from the jump. In her real estate literature, she guaranteed that she would buy any home not sold in 120 days with cash and claimed to service customers with no deposit and poor credit. Ads in the Stouffville Sun-Tribune featured photos of Simpson beaming, her hair a jumble of blonde curls, her smile daring readers to buy what she was selling.

Over the next several years, Simpson expanded her brand throughout Stouffville and beyond. But life wasn’t progressing as quickly as she’d predicted. She wasn’t rich, famous or broadly respected. She was a real estate agent, and an average one at that. So Simpson hatched a plan. Real estate wasn’t as hot in the early 2000s as it is these days, but the market was on the way up. The people she interacted with had money to invest but no real sense of what to do with it. She knew the language of real estate, and she was convincing. So she set up an investment fund tied to pre-construction properties and convinced some friends and acquaintances to try her out.

Related: Subscribe to Toronto Life’s new newsletter, Curb Appeal, for the latest in GTA real estate news

To reel them in, Simpson enthusiastic­ally laid out how her model worked. Through her, investors would provide interim funds, at a high interest rate, to people who had bought pre-construction condos. Buyers of pre-development condo units can begin paying their mortgages only once the entire building is finished, but they can live in their units if they pay occupancy fees—fees that Simpson told her investors their money could cover in the form of a loan. In return, investors would start receiving monthly dividends on the loan, as much as 25 per cent a week.

Eventually, Simpson had dozens of new clients. She used investment capital as fake dividends for the original invest­ors, then repeated the process as her clientele grew. By 2005, she had more than 60 clients who believed they’d found a get-rich-quick scheme and were totally unaware that they had instead walked straight into a classic Ponzi scheme.

In the early spring, flush with capital and with a growing reputation as a savvy financial mind, Simpson moved her office to a two-and-a-half-storey red-brick Victorian flanked by mature trees on Stouffville’s Main Street. It was the crown jewel of her personal real estate portfolio, which already included two residential properties in Stouffville and a cottage in northeastern Muskoka. She had often admired the Victorian and its rounded porch on her childhood walks to and from school, and buying it for herself made her feel like she’d finally made it.

In 2005, Simpson was charged for selling this commercial plaza on Stouffville’s Main Street to 100 different investors simultaneously. Photo by Lucy Lu

Around the time of the move, Simpson met a woman I’ll call Emily. (She requested anonymity, fearing personal and financial retribution from Simpson.) Emily knew people who had invested with Simpson and were pleased with the returns, and Simpson asked her if she was interested in doing the same.

Emily was reluctant to tie up a big chunk of her savings, but Simpson promised that she could get the principal back anytime. So, despite her initial reservations, Emily invested $100,000. Simpson seemed put together, and she was evidently very good at what she did, telling Emily that she had a buzzing office full of high-performing agents. In addition to being a convincing salesperson, Simpson had a girl-next-door quality that made her appear trustworthy. She regularly inquired after Emily’s kids and invited her over for backyard barbecues. “She was sincere, sweet and caring,” says Emily.

Their friendship began to sour in the fall, however, when Emily stopped by Simpson’s work one weekday and found it empty except for a receptionist. The place seemed half-deserted and barely functioning. Then, after sending along the first few monthly dividends of 10 per cent—$10,000—on time and as promised, Simpson began skipping payments. Suddenly, Emily was having to chase her for the dividends, only to be told, “It’s coming.”

About six months after her initial investment, Emily told Simpson that she wanted out and asked for her $100,000 back. Simpson tried to dissuade her, eventually negotiating her down to 50 per cent. But, when Emily tried to collect, she was ­stymied. Simpson would promise to have the cheque “tomorrow,” or she’d tell Emily to drop by the office and then never show up. After weeks of phone calls and staking out Simpson’s home and office—even confronting her at a local bar—Emily was finally able to claw back $50,000.

One morning not long afterward, her phone rang. It was Simpson, sobbing and apologizing. Emily demanded to know what was going on. “She said, ‘None of it’s real,’” Emily recalls. “‘There are no condos. There’s nothing.’” Simpson told Emily that the rest of her investment was gone and that she had to get off the phone to turn herself in to the police. Then she asked Emily if they could still be friends. That was the last time the women spoke. “She tried calling me after that, but I never answered,” says Emily, who went to the police herself.

The judge described her casualties: people who could no longer retire, no longer send their kids to university, no longer buy a home.

Another investor, also an acquaintance of Simpson’s, handed over $100,000 in late 2002, after she told him that she wanted her friends to share in the wealth that she and Wayne were enjoying. At first, as with Emily, things went smoothly. But, within a year, Simpson’s payments had slowed down, and she stopped returning his calls. The investor pushed back, demanding more than once that she close his account and return his funds. After Simpson claimed repeatedly that lawyers were finalizing the documents required to shutter his account, he hired a private investigator who learned that she hadn’t made a single call to a lawyer. It was only when he threatened to go to RECO that Simpson returned his initial investment.

As Simpson struggled to pay off her condo investors and keep her Ponzi scheme afloat, she embarked on a new scam: hawking enticing not-yet-listed commercial properties in and around Stouffville, then collecting deposits from multiple buyers. The bulk of the activity surrounded the same two properties, one of which was a plaza in Stouffville that Simpson sold to 100 different investors, all of whom thought that they alone had bought it. But the real owners had never dealt with Simpson, nor had they even put their properties up for sale. She had created fraudulent listings and contracts to make it appear as though the properties were on the market and she was the agent of record.

Soon, large sums of money were flying back and forth between Simpson and her investors, with bank records showing months where millions of dollars were both deposited and withdrawn. To keep RECO investigators off the trail, she falsified trust ledgers and banking information. Increasingly desperate for money to settle up with her original group of investors, Simpson took out pricey private mortgages against three of her personal properties. At one point, she was paying between 260 and 520 per cent annual interest on the debts and juggling funds between more than two dozen commercial real estate accounts.

Related: Inside a Bridle Path real estate scam that left a trail of victims, $17 million unaccounted for and one young lawyer in hiding

By early November of 2005, around the time that Simpson had her final call with Emily and turned herself in to the police, the authorities had been investigating her for two months. RECO revoked her real estate licence and the registration for her brokerage and ordered a freeze on her company bank accounts. In total, Simpson’s schemes amounted to almost $15 million in losses, included more than 140 victims and resulted in 23 charges against her.

She was released from custody in December on a $400,000 surety but faced an array of conditions: she would have to remain in Ontario and report to police every two weeks, and she was prohibited from soliciting money for future investments. Though her plans for a real estate empire were crumbling, she wasn’t about to give up. When interviewed by the local paper, Simpson was unrepentant. The fraud, she said, was overblown, and she was eager to make her investors whole.

In April of 2007, Simpson was sentenced to five years in prison and ordered to pay restitution of $4.5 million. The court-ordered receiver was able to recover $11.5 million through the liquidation of Simpson’s assets, including the two residential properties, the cottage and the Victorian that housed her office. She was sentenced to a further two years in prison, to be served concurrently, after pleading guilty to charges under the Real Estate and Business Brokers Act, including falsification of trust ledgers in order to conceal the nature of transactions, obstructing an investigator and providing false banking information to RECO.

“Ms. Wallis-Simpson has left a trail of financial devastation behind her with little or no motive that I can conceive of other than to enjoy a somewhat lavish and self-indulgent lifestyle,” suggested Crown attorney Paul Tait. When given a chance to address the court through her lawyer during the sentencing hearing, Simpson admitted that she’d made mistakes but quickly pivoted to her hardships. She was her family’s breadwinner and the primary caregiver for her eight-year-old son. She had lost her homes and cottage. She said she was a vital member of the Stouffville community and was in the midst of writing reference letters for 12 girls in her daughter’s graduating high school class. She insisted that the Ponzi scheme had been set up in a panic after she’d found that funds were mysteriously missing from a trust account containing the invest­ors’ deposits. (She would later concoct an outlandish narrative, blaming two mysterious businessmen from Dubai who stole $3 million from her. They also, she claimed, threatened her by slashing her tires and breaking the windows at her office before disappearing.)

Justice Howard Chisvin didn’t buy her sob story. “I’ll tell you quite frankly that I have no sympathy for you at all,” he told her. “I think you’re a very, very smart woman. I think you’re a very manipulative woman, and I think what you are trying to do is manipulate the process further.” He described her casualties: people who could no longer retire, no longer send their kids to university, no longer buy a home. “You’ve destroyed far more people along the way than you are even prepared to recognize at this point in time.” When the judge announced her five-year sentence, the courtroom erupted in applause.

Simpson served her time at a federal institution in Kitchener that she describes as “summer camp,” with McDonald’s and Caribbean food nights, and where she worked as a cook. In November of 2008, after serving a reduced sentence typical of a first-time, non-violent offender, Simpson was released on parole to a halfway house in Barrie—but she didn’t stay out of trouble for long. On April 14, 2010, Simpson entered her family’s home, which she was prohibited from visiting. She was arrested and returned to jail for 60 days for breaching her parole.
By 2012, Simpson was fed up with Stouffville. “A lot of people hate her,” says family acquaintance Wayne Lambert. “If you mention Courtney’s name, people will say, ‘Whatever you do, don’t get involved with her.’ ” Simpson moved to Bracebridge. She petitioned to have her real estate licence reinstated but was denied. Soon, her husband got his realtor’s and broker’s licences and set up Wynn Realty Corporation. This opened up a whole new avenue of opportunity for Simpson: she decided she would pitch herself as a real estate consultant. Officially, that meant nothing—it’s not an industry term—but, practically, it allowed her to act like an agent without the ramifications of actually being one.

After a few years in Bracebridge, Simpson grew bored. She wanted to move back to the Stouffville area, the one place that felt like home, even after everything. It was a bold and bizarre choice: on the one hand, she had plenty of connections there, but on the other, she had swindled many of them. The couple settled in a gated community backing onto the Wyndance Golf Club in Uxbridge, where they rented a five-bedroom, seven-bathroom home. By January of 2019, Simpson was showing properties for Wynn Realty—mostly vacant land available for development projects at below market value, upping the appeal—and collecting deposits of between $50,000 and $300,000 from buyers like Dundas Kwok through allegedly fraudulent transactions. It appeared to be the same old ruse, only this time she wasn’t even accredited.

In the fall of 2020, Simpson approached a new potential client, a broker from Toronto. She pitched him four plots of land in the GTA—stretching from Brampton to Milton—on which he could build single-family homes or townhomes. He had met Simpson through an acquaintance working in real estate and liked her immediately. “She was a very pleasant, astute person,” he says. Under the impression that she was a licensed realtor working for a licensed brokerage, he plunked down a total of $350,000 in deposits on the land—all conditional and refundable.

Wallis-Simpson meeting Pierre Poilievre. Photo via Facebook

When the conditional period elapsed without a deal, the broker naturally expected to get his deposits back. But, knowing how much he liked the deal, Simpson convinced him that she could extend the term, which she claimed to do more than once over the next few months. When the broker firmly insisted on the return of his money, Simpson told him she had dropped a $100,000 cheque in the mail and even showed him a receipt from Canada Post. “I was driving the Canada Post people crazy asking about this cheque,” he says.

The money never arrived, and Simpson’s only explanation was that it must have gotten lost. Soon afterward, aware that she’d stretched the limits of credibility, she stopped answering his calls. Bewildered, the broker filed a police report. With hindsight, he admits to having been fooled by Simpson’s ability to persuade, deflect and build trust. “She pulled the wool over my eyes,” he says.

When the reckoning finally came for Simpson, it started with her husband. On June 25, 2021, RECO put out a public advisory regarding Wayne and Wynn Realty Corporation, whose licences were immediately suspended for failure to refund consumer deposits upon request, as required by the Real Estate Business Brokers Act. The police investigation kicked off more than eight months later, in March of 2022.

Last July, Simpson and her husband were hit with more than 100 charges. At Simpson’s first court appearance, on September 12, she hadn’t yet retained counsel and told the court that she and her husband likely wouldn’t have rep­resentation until October. At a November 7 hearing, the couple still didn’t have representation. This time, Simpson blamed an injunction that had frozen their assets. She claimed that she was working with legal aid but hadn’t been assigned a lawyer. When Simpson still didn’t have a lawyer at a March 6 hearing, the judge had had enough, ordering her to prepare to represent herself at a pre-trial in July.

Simpson’s legal troubles mean little to Kwok, who scoffed when I asked if he thought he would get his money back. It has been more than two years since he handed over $250,000, and he has yet to see a dime from Simpson. (His deposits are insured by RECO up to $100,000, but it is unlikely that anything can be paid out while the case is before the courts.)

Meanwhile, in a bid to repair its credibility, RECO is working to address recommendations made in the auditor general’s 2022 report. Proposed fixes include a new, more stringent broker inspection program and more-assiduous tracking and reporting of inspections. RECO will also reevaluate how and when criminal background checks on agents and brokers are conducted.
When Simpson finally agreed to meet with me in person late last December, she arrived in a royal-blue silk dress, her shoulder-length blonde hair in a blowout. She was polished, smiling and polite. I could see how people would be taken in by her manner. In our previous email correspondence, Simpson had implored me to be gentle with her, citing all the criticism she’d endured. Sitting across from me, she asked if she could read something she had written, then launched into an elaborate and rehearsed script, describing herself as “freshly 57, a very happy smile on my face and always a spring and a skip in my step.” A series of eclectic descriptors ­followed—honour-roll student, gardener, yeoman and the “person who invented ‘Pay for the person behind you’ at Tim Hortons in Stouffville in 2000.”

Then came the tragic backstory: at the age of 16, she was in a devastating car accident that smashed every bone in one side of her body, leaving her dangling over a bridge, then fully immersed in a frigid river. She mentioned miscarriages, infidelity, financial troubles and being the first Brownie in Canada to win a “golden pin” for selling the most cookies. She claimed that, when she was arrested in 2010 for violating her parole, officers pressed her face into the “sweltering July pavement” while pointing guns at her head, in view of her son and his friends. She had been slandered, lied to, neglected, tricked and bullied, she continued, and had endured receiverships, threats, battles, sneers, lawsuits and revenge plots.

And yet, she told me, she has overcome. She was an angel investor, a healer, a helper, a mentor and a friend on the cusp of finding her new purpose. In the time since her most recent arrest, she had written and self-published For the Love of Cheesecake, the first volume in a forthcoming series of cookbooks—her latest passion.

Over the course of our three-and-a-half-hour conversation, Simpson dodged and deflected many of my questions, giving coy half-answers over and over and ­blaming trauma for her memory lapses. Regarding the 2022 charges, she suggested that it was all a big misunderstanding. She claimed that a $500,000 deposit she had paid a developer in an effort to buy a building in Bracebridge had been frozen as he battled his own allegations, keeping her from working on the building and turning a profit. This is what led her to bounce cheques and unwittingly set off yet another cascade of legal and financial woes. When I followed up with the Peel Regional Police, they said the name of the developer Simpson shared with me hadn’t come up in their investigation.

Courtney Wallis Simpson and her husband, Kenneth Wayne Simpson, are facing dozens of charges for allegedly collecting millions in deposits between 2019 and 2021 on properties they weren’t authorized to sell. Photo via Facebook

During our conversation, there was one thing Simpson was categorical about: Wayne’s innocence. She said he had never been involved in the transactions now under scrutiny. He was retired and had been for a while, and he had only come to a few meetings at Simpson’s behest. (The people I spoke to who filed police reports related to Simpson’s most recent charges described Wayne as a peripheral player; some had never even met him.) “He’s just a nice, gentle, completely honest guy,” she said.

Wayne—whose only dream is to buy a cottage in Haliburton, go fishing and never come back to Stouffville, according to a long-time family acquaintance—agreed to answer my questions via email. He described the dozens of fraud charges as “the situation Courtney is facing” but verified her version of events about the men from Dubai and the threats to her life. Wayne says that Courtney took the blame against his explicit advice, but she was just so determined to make things right for the people who had entrusted her with their money. If she has one flaw, it’s that she’s “an exceptionally trusting person,” he wrote. “I cannot change her generous and trusting nature, or her fierce determination to correct the wrongs that were imposed upon her by dishonest and calculating men who were determined to take advantage of her.”

I wondered how much Wayne knew about his wife’s conduct and whether he understood just how much trouble they were both potentially in. I wondered whether they would bother to secure a lawyer before the pre-trial in July. And I wondered if Simpson had actually written that email herself, posing as Wayne and using it as yet another opportunity to advance her own agenda.

Before we parted, Simpson told me that she had a much better story for me. She slid a stack of paper, held together by a large binder clip, across the table, releasing a stale vestige of cigarette smoke. It was the auditor general’s report on RECO, which spelled out the loopholes and regulatory failures in the real estate game. “There’s so much corruption within the industry,” she told me, without a trace of irony. “It’s mind boggling.”

This story appears in the June 2023 issue of Toronto Life magazineTo subscribe for just $39.99 a year, click here. To purchase single issues, click here.