Dead Reckoning

As a boy, Sami Suomalainen often walked to the beaches of Helsinki and dipped his hand in the Baltic. He imagined the water stretching to the shores of Africa, Asia and the Americas, where he pictured other kids with their hands in the sea. He dreamed of crossing oceans to meet them, but he was stuck in post-war Finland, one of three boys born to a nurse and a copywriter. Instead, he painted the fantastical worlds he hoped to one day see in person.

At 15, Sami set down his brushes and went looking for adventure. He joined the Finnish Navy and then spent several years hauling cargo on merchant vessels working the ports between Miami and Montreal. When he returned to dry land, he chose Toronto, which reminded him of Helsinki. Yorkville’s bohemian scene was roaring, and Sami fit right in, taking art classes, attending gallery openings and dancing with young ladies at parties held by various European clubs.

It was at one such event that Sami met June, a gregarious Englishwoman who shared his wanderlust. A midwife from the dirty Dickensian outskirts of Manchester, she’d left her industrial hometown as quickly as she could, working at hospitals and clinics in Fort Worth, Philadelphia and Toronto. June was taken with Sami, the Scandinavian with Mick Jagger hair, and visited the library to research Finland so she’d have something to talk about on dates with him. Sami was equally enamoured of June, the feisty, upbeat Brit. When she got a contract at a hospital in Chicago, he drove nine hours in his jalopy to visit her. They got married in 1966 and never stopped exploring—running around Brussels and Buenos Aires, visiting family in the UK and Finland, sunbathing in Cuba, and camping in Algonquin.

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Toronto became their home base. In 1975, June and Sami bought a charming brick semi near Yonge and Eglinton and filled it with cats—Sami loved to plop them into the pocket of his painter’s smock. He made a living as a commercial artist, contributing editorial cartoons to magazines and newspapers and drawing furniture, saunas and canoes for print advertisements. In 1979, he illustrated Mud Puddle, the first of Robert Munsch’s best­selling children’s books, and his career took off. The Canadian Art Archives acquired some of his work, and galleries across Toronto exhibited his dreamy canopies and seaside scenes full of boats, birds and characters borrowed from Nordic folklore. Sami painted every day, either at an easel in the sunroom or in what June called his “atelier,” a second-floor bedroom overstuffed with pigments, palettes and canvases. There was even more art in the basement: hundreds upon hundreds of paintings, drawings, frames, ­ceramics, sculptures, glassworks and wood carvings. Sami was tireless. Most days, even in his 70s, he biked down to his favourite coffee shop in Kensington Market. June, no less energetic, worked as a nurse at St. Michael’s Hospital until she was 73. She was beloved for hosting brunches and dinner parties for an eclectic circle of friends that included artists, health care workers, professors, tennis players and a former Swiss Guard.

When June first suggested making a will, Sami resisted. He was a private person, and he didn’t like talking about money. But, in the summer of 2013, she convinced him to walk to the nearest law office and get it over with. When they stepped inside Schwarz Law Partners, a firm near Yonge and Davisville, they were directed to an associate named Robyrt Regan. Just shy of 50, he was warm and affable, a gifted conversationalist with slicked-back hair and a quick smile. He asked Sami and June about their lives and careers before cataloguing their assets: the house, everything in it, several bank accounts. Together, it amounted to more than $1.3 million. They’d never had kids, so they asked Regan to draft a will that would divide and distribute their estate equally between five beneficiaries: Sami’s two nephews in Finland, June’s two godsons in the UK and the son of June’s best friend in Toronto.

Sami and June also needed to appoint an executor, someone to carry out the wishes in their will. Regan seemed like a safe choice—he was a neutral third party and an experienced professional. So they wrote him in, signed the will and forgot all about him. Likewise, Regan forgot about Sami and June. He soon had more pressing concerns on his mind. Three days after he was appointed executor, one of his other clients sent him an email that read, “Mr. Regan…I am preparing various proceedings at present to deal with your fraud and put you in prison.”

That man was Bob Bortolon. In 2007, he had walked into Robyrt Regan’s office seeking legal advice. Six feet tall, bald and imposing, Bortolon ran an auto shop in Bolton and needed help resolving a dispute with his landlord. Regan and Bortolon clicked. They had both recently married, and they shared an affinity for classic cars. Regan collected antique Cadillacs; Bortolon bragged that he’d customized a convertible for MC Hammer.

Both men were trying something new. A Vancouver native, Regan had studied theatre at UBC and then ran his dad’s publishing company, selling postcards and souvenir books to local gift shops. When the internet threatened his business model, Regan moved east, studied law at Queen’s, got called to the Ontario bar and began building his legal career. Bortolon had baggage: in 2002, while running an auto shop in Arizona, he’d been convicted of multiple counts of insurance fraud and sentenced to five years in prison. He told Regan he was the innocent victim of a vast network of crooked judges, cops, realtors and insurance companies who had conspired against him. In any case, he’d served his time, been deported to Canada and was eager to rebuild.

Soon, Regan and Bortolon were professionally and personally enmeshed. Regan became corporate counsel for Bortolon’s auto shop. Bortolon helped Regan and his wife, Cathrine, move into a house in suburban Hamilton. The Regans regularly hosted the Bortolons for dinner, and when Cathrine had a baby girl, Bortolon showered her with gifts.

In the early 2010s, however, the relationship began to strain. The Business Development Bank of Canada took Bortolon to court for failing to repay a $100,000 loan. To pay Regan’s mounting fees, Bortolon took out a $50,000 mortgage against the auto shop. Bortolon also recompensed Regan by servicing his cars, renovating his basement and granting the Regan family a 40 per cent stake in his business. But the two men eventually began to bicker about who owed whom. Bortolon demanded cash for the reno and refused to return one of Regan’s cars. Regan, still owed tens of thousands in fees, gave Bortolon an ultimatum: return the vehicle or he’d quit.

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From there, the squabble only escalated. Bortolon hired another lawyer to put a $50,000 construction lien on Regan’s house. Convinced the lien was illegal, Regan mailed the new lawyer a Monopoly card that read, “Go directly to jail. Do not pass Go. Do not collect $200.” Regan then used his stake in Bortolon’s business to mount a hostile takeover of the auto shop, making himself the company’s sole director, terminating its lease, rerouting its mail and depositing its cheques into a new bank account.

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Sami and June needed an executor, someone to carry out their wishes. Regan seemed like a safe choice

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The same week Regan signed the Suomalainens’ will, he proposed a truce with Bortolon: he’d discharge the mortgage and return his shares of the auto shop if Bortolon paid his legal fees, returned his car and withdrew the lien. “And then,” Regan wrote, “I can tell my three-year-old daughter that Uncle Bob simply ‘borrowed’ her car seat and toys (which are still in the car) for a while rather than telling her you are a bad man who stole her car seat and her toys and threatened to harm her mummy and daddy.” Regan later alleged in court documents that, shortly thereafter, someone matching Bortolon’s description walked up Regan’s driveway and broke into his other car, scattering his daughter’s car seat, toys and other contents across multiple lawns.

Amid the ugly quarrel, a fire engulfed the auto shop. It fell to the courts to decide where the insurance money should go: to Bortolon, to Regan or to the Business Development Bank, which was still trying to recoup its $100,000 loan. A judge ordered Regan to produce the auto shop’s business records, which Regan believed would incriminate Bortolon. Regan proposed a trade: he’d give Bortolon the incriminating files if Bortolon returned his car. At some point during the swap, several boxes of records went missing, preventing any possibility of a fair trial. The courts found both men in contempt and sentenced them each to 45 days in prison. When Regan received his sentence, police officers walked into the courtroom, arrested him and escorted him to Maplehurst Correctional Complex.

It was only the latest in a string of bad turns for the lawyer. He’d already been fired by a client in the halls of the Brampton courthouse for accepting a settlement without that client’s consent. In 2014, Regan joined a Bay Street firm called Chappell Partners, where he fell short of his billing targets. When management criticized his performance, he went on the defensive, complaining that the firm wasn’t referring enough work to him. “With all due respect,” Regan wrote in an email, “this is reminiscent of an old Keystone Kops movie, where the villains dynamite the railway trestle and then complain when the train fails to arrive at the station. The partners have nobody to blame but themselves.”

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Regan then began sending the firm’s partners inflammatory letters from a newly formed company, Chappell Regan Professional Corporation, that cribbed Chappell Partners’ logo and letterhead. In one, he wrote, “When my five-year-old daughter asks how snakes are able to move along the ground, I will tell her to come to a Chappell Partners meeting so she can see what slithering looks like.” Regan evoked his daughter again in a human rights complaint against Chappell, alleging that the firm had implied he wasn’t “partner material” because he was a working parent. He complemented that complaint with an $8.5-million lawsuit that described his former employers as “petty, childish, cowardly and unbecoming.”

In 2017, the Law Society of Ontario, having received multiple complaints about Regan, arranged a disciplinary hearing to determine whether his licence to practice law, already suspended because of the contempt finding, ought to be revoked altogether. Regan called the inquiry a “witch hunt” and slowed the pace of proceedings to a crawl by refusing to produce relevant evidence, requesting adjournments, filing last-minute motions and appealing judgments. After an eight-year slog that cost the Law Society more than $300,000, the tribunal declared that Regan had “knowingly assisted in dishonesty, fraud, crime or illegal conduct.”

When Regan was offered a final chance to apologize and purge his contempt, he instead lamented that he’d had to remove his daughter from private school, sell his sailboat and forgo family vacations. Unmoved, the Law Society disbarred Regan and ordered him to pay a $150,000 penalty, writing, “We conclude that to allow the Lawyer to continue to practise in any legal role, part time, pro bono or otherwise, would put the public at significant risk.”

In 2019, unable to practise law and in desperate need of income, Regan received word that Sami and June Suomalainen had died. June had received a diagnosis of cervical cancer in April. Over breakfast one morning in July, she told Sami, “You’ve got beautiful hair” and had a stroke. Without her, Sami was lost. He hardly knew how to work a stove, let alone cope with the grief. He tried to stay busy, continuing to teach art classes at a Finnish retirement home and visiting neighbours. But, two months later, he dropped dead in the atelier, brush in hand. Medically speaking, it was a cardiac arrest, but his friends and neighbours told me he died of a broken heart.

That December, the Office of the Public Guardian and Trustee asked Regan if he still intended to serve as the executor of the Suomalainen estate. That his legal licence had been suspended did not disqualify him since a layperson is allowed to be an executor. Non-professionals often agree to take on the role for friends or family members, assuming it will be a straightforward process, only to discover, upon their loved one’s death, that the job is far more involved than they had anticipated. It can be financially taxing: executors sometimes find themselves covering estate expenses—funerals, burials, ongoing bills—and waiting years to be reimbursed. The job also demands time and tenacity. People rarely leave tidy summaries of their holdings, accounts and passwords. Rather, executors have to sniff out assets, sort through documents, correspond with banks and insurance companies, file reams of paperwork, attend court, discard and donate furniture and clothing, locate and inform beneficiaries. If an executor is lucky, those beneficiaries help the process along. Just as often, inheritors are yet another occupational hazard—unresponsive, uncooperative, mired in long-simmering family feuds. And so what begins as a favour to a friend can end up becoming a slog through a thicket of grief and greed.

In recognition of the effort required, executors in Ontario typically receive up to five per cent of an estate’s value. But that perk can also evaporate. When a Toronto accountant named Terry Dooley agreed to be executor for a multimillionaire client in 2010, he thought he was signing up for a job that would pay $375,000. Instead, the client’s daughter, upset that she had been excluded from the will, took the matter to court. After years of litigation, Dooley ended up with a six-figure legal bill, not a payday. “People turn into creatures you don’t even recognize when there’s money on the table,” he told the Toronto Star.

But executors aren’t always the victims; sometimes they’re the perpetrators. In 2007, a lawyer named Geoffrey Zimmerman became trustee for the $5-million estate of Robert and Signe McMichael, the Group of Seven collectors who founded the McMichael Canadian Art Collection. Zimmerman was supposed to give everything to the gallery and various charities. Instead, he spent lavishly, dining on lobster and lamb chops at fancy restaurants and treating the McMichaels’ vacation property in Florida as his own family’s winter getaway. When the McMichaels’ niece sought to hold him to account, he ignored judges’ orders, missed hearings and burned through lawyers. In the end, Zimmerman was ordered to pay $870,000 in penalties and restitution.

Shortly after hearing from the Office of the Public Guardian, Regan accepted the role of executor. A few days later, he received the keys to Sami and June’s house. Regan then wrote to Antti ­Suomalainen, one of the two nephews named in Sami’s will. He introduced himself as his uncle’s former lawyer and offered his condolences. Antti and his brother, Jaakko, hadn’t seen Sami often, but they thought of him fondly. His art decorated their childhood home, and Sami used to bring them NHL jerseys when he visited Helsinki. Jaakko, who had played in Finland’s pro league, once outfitted his goalie mask with one of Sami’s paintings of a bearded harpist from a Finnish epic poem. They were sad to learn of their uncle’s death but relieved that a professional was handling the estate; they felt unequipped to settle his affairs from overseas. “We have very little ­experience with anything like this,” Antti told me. “We trusted that everything would be done properly and honestly.”

Regan gave them no reason to suspect otherwise. In a series of businesslike emails, he detailed his plans: cremate Sami’s body, arrange a funeral and burial, find the other three beneficiaries, and pay the couple’s outstanding bills and taxes, which included $100,000 Sami and June had borrowed from CIBC to replace their windows in the 2010s. Regan stressed that, in order to legally sell the house, he needed probate—that is, a certificate from the courts legally appointing him trustee of the Suomalainen estate. And to apply for probate, he explained, he needed to determine the value of the estate, which in turn required him to obtain professional appraisals of both the house and Sami’s body of work. It would take time, of course. But, even after Covid hit, delaying the process, Regan told Antti and Jaakko to expect a distribution by the end of 2021.

In the meantime, Regan provided the Finns with periodic updates. To satisfy the insurance company and prepare the house for market, he explained, he was visiting the property regularly, installing a security system, fixing leaks, and replacing old wiring and broken gutters. Regan also tried to tie up financial threads, collecting June’s and Sami’s pensions and the latter’s royalties from Mud Puddle and the other kids’ books he’d illustrated. And then there was the art—roughly 2,500 paintings, by Regan’s count. He hired a student to photograph each work and record its title, vintage, dimensions and other details so that an appraiser could price the entire collection. She issued her report in July of 2022, estimating Sami’s oeuvre to be worth $53,000 “as is, where is” (sold in its current condition and location) or $330,000 “at fair market value.”

By then, the nephews were anxious to wrap things up. It had been nearly three years since Sami’s passing. But Regan offered reasonable explanations for every delay: the overwhelming volume of art, a pandemic-induced backlog at the courts, a car accident that required him to take time off. Regardless, the end seemed to be in sight. By the fall of 2022, Regan had determined the value of the estate, located the three other beneficiaries, found a lawyer to apply for probate and finally held Sami’s memorial, at a Finnish church in North York. He was introduced as “Sami’s friend” and delivered a eulogy on behalf of Antti, Jaakko and their mom. Regan’s wife and by then teenage daughter read from Corinthians. At the end of the service, Regan and Cathrine carried Sami and June’s ashes down the aisle and into the parish hall, where Regan had set up some of Sami’s artwork. “The paintings you see on the wall are for sale, as is the remaining artwork that is in the house,” he announced.

Watching the funeral online, Antti and Jaakko felt uneasy. In his emails, Regan had casually mused about submitting Sami’s art to auction houses, publishing a book of his cartoons, even preserving Sami’s house as a gallery. He claimed the collection could be worth $1 million. The brothers weren’t so sure—they were under the impression that Sami had struggled to sell his paintings. “Since Sami is not a world-famous and widely popular artist, the potential group of buyers is quite small,” Antti told me. And now Regan was hawking Sami’s art at his funeral. “None of us asked for anything like that.”

Antti and Jaakko’s doubts deepened after the memorial, when Regan went quiet for months. In the spring of 2023, Jaakko pushed for answers. “At the moment we are quite confused about the status of the process,” he wrote. “It has been almost four years now since Sami’s passing and we know Covid slowed things down but it just seems a very long time.” He requested a copy of the will, the probate certificate, and an accounting of the estate’s assets and expenses. “Is it a part of the will that you find a gallery to house or store the art?” he asked. “Has any art been sold and at what price? Can you give an estimate of how long this whole process will still take?” Regan wrote back, promising to prepare a detailed report. One week later, his lawyer, Amanda Groves, provided a copy of Sami’s will and a freshly filed probate application. Finally, Jaakko thought, things are coming to a close.

While the probate application was being assessed, however, Regan escalated his efforts to sell Sami’s art. The longer things dragged on, the more Regan—who was charging $117.50 an hour—earned. Later that year, he rented the first floor of a multi­coloured Kensington Market storefront and hung dozens of Sami’s paintings on its bright-blue walls. The gallery also featured the work of a 19-year-old University of Toronto student, one of three young women Regan hired to staff the space, manage its social media accounts and plan events. The gallery’s launch party, in July of 2024, was the student’s first public exhibition, and the place was packed. Guests sipped wine, grazed vegetable platters and admired the grand piano in the centre of the room—oblivious to the fact that the landlord was on the brink of evicting Regan.

Regan was renting the space from Peter Waldmann, the lawyer who had represented him during the Law Society hearing, whose offices were above the gallery. He immediately fell behind on rent. By the launch party, he was $42,000 in arrears, and Waldmann was running out of patience. One week after the event, he sent Regan an email with the subject line, “ENOUGH IS ENOUGH,” threatening to terminate the gallery’s lease and seize its contents in two days if Regan didn’t pay up.

Rather than settle his debts, Regan instructed gallery staff to move everything to Sami and June’s house. They managed to remove the art, but they couldn’t find a piano mover on such short notice; Waldmann took the instrument hostage, demanding that Regan pay $15,000 to get it back. In response, Regan’s wife, Cathrine, launched a lawsuit against Waldmann, asking the courts to order the return of the piano, which she said belonged to her. The parties eventually settled, with Waldmann releasing the piano and Regan paying roughly $13,000 in rent.

When Regan emailed Antti and Jaakko about the gallery that fall, he framed it as a win for the estate. “I am pleased to advise that my efforts to market and sell Sami’s paintings have been largely successful,” he wrote, making no mention of the eviction or the lawsuit. He explained that he’d closed the Kensington location and moved the artwork back to Sami’s house, which he’d opened to the public. Now, he said, he was turning his attention to throwing a gala in the house, selling more works at the Finnish church, opening a holiday pop-up, and arranging exhibitions in New York, Chicago and LA. He neglected to remind them that his hourly rate was continuing to tick along.

The brothers might have balked at these details had Regan’s update not contained an even more explosive bombshell: he’d sold the house to a “real estate investment company” that had agreed to temporarily lease the space back to the estate until everything wrapped up. Antti and Jaakko were dumbfounded. For years, Regan had insisted that he needed probate to sell the house. And now, without it, the house was gone. On top of that, Regan still hadn’t provided any information on how much art he’d sold, shared any accounting or indicated how much longer the process would last. The brothers felt helpless in Finland, far from the action. They pulled up the will and checked the names of the other beneficiaries. It was time to call for backup.

Ian Young had not, at that point, received a single email from Robyrt Regan. All he had was one letter from Regan’s lawyer, Amanda Groves, informing him that Sami had left him a gift and that the probate process was underway. Young, whose mom was June’s best friend, assumed that meant everything was in order. By the summer of 2024, however, Young started wondering why the estate was still unsettled, so he reached out to Groves for Regan’s number and gave him a call. Regan said he’d be happy to chat and invited Young to meet him at Sami and June’s house.

Young had plenty of memories inside that house—Sami drawing him, June cooking for him. When Young was a kid, the couple babysat him so often that the spare bedroom felt like his own. But, when Young and his mother, Alison, walked in the front door that September, they barely recognized the place. The walls were yellow; all the furniture had been replaced. There were several pairs of shoes by the door, and there was a young woman milling about, staffing what appeared to be a gallery. On the wall, Young noticed a painting he’d hoped to inherit; it was priced at $14,000, more than any of Sami’s works had ever fetched.

Regan greeted the Youngs with a smile and told them he was seeing incredible interest in Sami’s art. Just the other day, he explained, a group of businessmen had been in the house to view the collection. And the fall exhibition, displaying Sami’s paintings alongside work by a Vancouver-based artist named Tom Carter, would open the following week. It felt surreal to Ian and Alison, but they tried to give Regan the benefit of the doubt—he seemed genuinely invested in Sami’s legacy. And Regan said he had good news: he’d sold the house. Young assumed that meant Regan had been granted probate and that the end was near.

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Regan offered to step down as executor—if the beneficiaries granted him the house and Sami’s art

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Soon afterward, Young heard from Antti and Jaakko, who informed him otherwise. The Finns explained that they were also in touch with June’s two godsons in northern England, Andrew Brooks and Simon Howcroft, neither of whom had heard from Regan either. Once all five men connected, they were stunned to discover that Regan had kept three of them in the dark for years. The beneficiaries quickly agreed to hire a lawyer, who helped them piece together a more complete picture of Regan’s activities as executor. It was true that he’d sold the house—but that was just a sliver of the story.

In October of 2023, Regan had transferred the property to himself in his capacity as the representative of the Suomalainen estate. Once the house was in his name, Regan immediately took out two high-interest mortgages totalling $260,000. The lender was a soon-to-be-imprisoned mortgage broker named Jason Georgopoulos, who was at the time awaiting trial for accelerating his Lamborghini to 112 kilometres per hour trying to pass a streetcar, crashing and causing permanent brain damage to his administrative assistant in the passenger seat. (Georgopoulos—who testified that he didn’t think he was speeding and hadn’t seen the parked cars—was sentenced to two and a half years in prison for dangerous driving.)

The beneficiaries also discovered that the “real estate investment company” that purchased Sami and June’s house was in fact a numbered company that had three directors: Regan; his wife, Cathrine; and Steven Salari, a restaurateur. Salari’s best-known restaurant, a defunct Italian joint in Yorkville called Coco Lezzone, had closed several years earlier after a series of attacks: a gunman shot Salari in the back in 2000, a bomber blew up the front window two years later, and in 2015 a vandal threw a can of pepper spray into the dining hall, causing guests to cry and vomit. To fund the purchase, Regan borrowed $140,000 from a Hamilton woman named Karen Briand, and Cathrine took out a $418,000 mortgage secured against the Regans’ Hamilton home and a small cottage they own in Leamington.

Regan knocked another $235,000 off the purchase price, considering it payment for his estate administration services and expenses to date. To make up the remainder, he arranged a vendor take-back mortgage of $521,000—that is, the estate loaned Regan’s numbered company more than half a million dollars to buy the very house it was selling. The interest payments on the take-back mortgage, payable to the estate, amounted to $2,600 per month. Regan also arranged for the estate to start renting the house back from its new owner for $6,950 a month. When the sale closed, not only did the estate lose ownership of the house; it also found itself paying the numbered company $4,350 a month to use the house as a gallery and storage space.

As the beneficiaries were wrapping their heads around all that, they noticed that the house was back on the market, this time for $1.6 million. Concerned that Regan was trying to flip it for his own gain, they filed a formal objection to Regan’s probate application. They also had their lawyer send a letter demanding that he provide “a full statement of accounts for the Estate within two weeks.” Thirteen days later, Regan sent the beneficiaries a tranche of invoices, receipts, bookkeeping spreadsheets and time dockets—the first of several document dumps that detailed what he’d been up to over the past five years. In an accompanying ­letter, Regan wrote, “I believe that once you have had an opportunity to review the accounts, communications and estate documents in detail, you will find that I have discharged my responsibilities in a proper, diligent and ethical manner.”

According to the documents, Regan had worked roughly 3,145 hours, which amounted to fees of just under $370,000. He’d spent at least $100,000 renovating the house, which his numbered company now owned, and he’d used more of the estate’s funds to rent and staff the gallery in Kensington Market. Regan also charged the estate for trips between Hamilton and Toronto—$36,750 worth of mileage and $20,475 in 407 tolls. And then there were hundreds of sundry expenses: “client development meetings,” sushi lunches, TTC and GO fares. Upon closer inspection, the beneficiaries realized that some of the vendors Regan hired to provide the estate with various professional services—Eastcourt Strategic Solutions, Reganlaw Management, RBS Global ­Capital—were owned by Regan. All told, under Regan’s watch, the estate had spent around $1.3 million—roughly its entire value. At the end of a 13-page letter outlining many of these costs, Regan wrote, “It has been my pleasure to serve you as Estate Trustee.”

In April of 2025, Regan and the beneficiaries agreed to meet over Zoom. The five men remained civil, but inwardly they were fuming. They wanted to press Regan for answers and map their way out of the mess he’d created. Brooks, a level-headed private sector consultant, led the meeting—he was the natural choice, having taken it upon himself to parse and organize all of Regan’s documents and act as the ­beneficiaries’ point person. When Regan entered the Zoom call, Brooks thanked him for joining them and told him that the meeting wasn’t meant to be adversarial. Regan told them he didn’t interpret it that way. “I liken this to a boat ride,” he said. As executor, he thought of himself as the captain, the beneficiaries his passengers. His job, he said, was to sail them safely to their destination. “We’re near that point…. Certainly I’m anxious to tie the boat up, and you’re, I’m sure, ready to disembark.”

Over the next 95 minutes, Regan assured them that every one of his actions had a reasonable explanation. It was perfectly legal for him to transfer the house into his own name, he explained, because of a quirk in Ontario’s land registry system. Besides, as he had told them in an earlier letter, the home insurer and mortgage lender required the house to be in his name. As for why he needed $260,000, he said the loans were necessary to repair the roof, which had been damaged in a windstorm. But the transfer of the property had unintended consequences, he continued, because it prompted CIBC to sue Regan for repayment of the $100,000 mortgage that the estate still owed the bank.

“In November 2023,” Regan said, “I woke up one day to a summons at my door from CIBC naming me personally in a foreclosure action against the matter of the property, which caught me terribly by surprise.” He said he had looked at “a whole series of really unpalatable options”: let CIBC take the house, list the house in what was then a soft market or arrange a private sale for the full appraised value of the home. “Should I have called everyone at the time and asked? In retrospect, that might have been a better idea,” he said. “But there’s a very short time here to do things, and the bank did not give me the luxury of having time to come to a perfect decision.” Now, he said, he was listing the house again so he could repay the estate’s take-back mortgage and make his other lenders whole. When the beneficiaries asked how he could do that without probate, he said—contradicting his early letters again—that he didn’t need it. All of his power, he argued, derived from Sami’s will.

Young then took aim at Regan’s fees, pointing out that they were exponentially more than what an executor would typically charge. “Sami was aware that my fees are by the hour. That’s all I have to say on that,” Regan shot back, adding, “As with all things in business, certainly things are open to negotiation.” He suggested they table that debate for the time being. The conversation moved on to what Regan considered the biggest barrier to settling the estate: Sami’s art. “If you panic-sell 2,000 paintings, you’re going to get a very limited return,” he said, so their best bet was to continue exhibiting and selling the work as he’d been doing. Howcroft brought up the possibility of simply donating the collection. But Regan said that would be “improvident” given that the estate did not have a sizable income to write off.

Before the end of the call, Regan said he would follow up with an exit strategy document proposing a way to wind up the estate once and for all. “I’d like to keep this on friendly footing,” he concluded. “There’s no acrimony on my end. I’m just trying to berth the ship and hand you your disembarkation cards. And then I can do what I want to do and go my way, and you guys do the same.”

Two weeks later, Regan wrote to the beneficiaries again, offering to step down as executor. Sami and June, he wrote, “would not want to see their memories obliterated in a sea of angry rhetoric between the beneficiaries and their estate trustee or their remaining estate assets depleted in unnecessary and costly estate litigation which will ultimately benefit nobody.” Therefore, he said, he would dramatically reduce his fees and resign—if, that is, the beneficiaries agreed to formally grant him ownership of the house and Sami’s art.

When the beneficiaries rejected those terms, Regan put the house back on the market, this time for $1.2 million. A young couple who had previously toured the property pounced, submitting a successful $1.3 million bid, signing a purchase agreement and putting down a $50,000 deposit. But Regan couldn’t clear title and obtain insurance, both of which were necessary steps to close the sale, without the written consent of the beneficiaries. So, in October of 2025, he hired a lawyer to email the beneficiaries, asking them to sign a release acknowledging that they “were aware of, and approved of ” the sale of the property to the numbered company—a request they again refused.

At that, Regan sent the beneficiaries a series of increasingly desperate letters, explaining that, if they continued to obstruct the sale, the take-back mortgage would never be repaid and the estate would have to file for bankruptcy. “Costs and damages will be sought personally from any beneficiary opposing these applications,” he wrote. “There is no financial benefit ahead for you or for me if we continue down the ‘litigation highway.’ ” The only way to avoid a court battle, he said, was to send him a signed copy of the release by December 5, 2025. “The deadline is firm.”

On December 5, as Regan was waiting to hear from the beneficiaries, he received other news: he was being sued—twice. The young couple who had tried to buy the Suomalainens’ house wanted their $50,000 deposit back. More significantly, the private lenders who had provided Cathrine with the $418,000 mortgage were pursuing legal action, threatening to take possession of both the Hamilton and the Leamington properties unless the Regans paid up. By January, Jason Georgopoulos was demanding that Regan pay him $302,000. Then Baker and Company, the law firm Regan hired to try to facilitate the sale to the young couple, asked the courts to compel Regan to pay $71,000 in overdue legal fees. Including the take-back mortgage, Regan was now roughly $1.5 million in the hole and, with interest, accruing $440 of additional debt every day. One way he could avoid losing his own homes and going bankrupt was to sell Sami’s house. And the beneficiaries were the only ones standing in his way.

This past January, Regan sued the beneficiaries, alleging that they had, “without good reason,” continually obstructed his attempts to sell the house and administer the estate. In his application, Regan asked the courts to legally recognize his numbered company as the rightful owner of Sami and June’s house. To make his case, he included more than a thousand pages of documentation, correspondence and legal analysis. Among the revelations in those pages: in May of 2021, Regan had, without informing the beneficiaries, declined a $1.2-million offer on the house that could have averted the fiasco in which he now found himself.

At the time this story went to press, Regan and the beneficiaries were still working their way through the courts. By the end of April, Regan had sent the beneficiaries more than 30 legal documents related to the case, including affidavits, factums, settlement offers, exhibits and costs outlines demanding that they pay more than $17,000 of his fees and disbursements. When I contacted Regan for an interview, he said the estate is currently the subject of a probate application and related proceedings and that the beneficiaries were provided with a complete accounting of the estate in March of 2025. He claimed that the beneficiaries have been unable to produce any documentary evidence in support of their allegations and that they refused to answer proper questions put to them. He also pointed out that no finding of wrongdoing has been made against him.

If and when a judge delivers a decision, there will be plenty of case law to draw upon. Imprudent estate trustees are known as “rogue executors,” and there’s no shortage of them. Over the past few years, Canadian courts have heard cases involving executors who used estate funds to buy personal real estate and bankroll extravagant vacations, who moved into the homes they were supposed to sell and failed to communicate with beneficiaries for 20 years. The case that may prove more relevant to Regan’s, however, is that of William Bishop, a disbarred lawyer who applied to become executor of his late friend’s estate. Though all five of the estate’s beneficiaries supported Bishop’s application, the courts barred him from becoming the estate trustee, in large part because the Law Society had found him guilty of helping his clients obtain more than a dozen mortgages under false pretenses. “Mr. Bishop…is no longer entitled to the presumption, without question, of being a person of integrity, probity and trustworthiness,” Justice Graeme Mew wrote. “This is one of those rare cases where the court should invoke its inherent discretion to decline an application for the appointment of an estate trustee.”

The courts may soon need to decide whether Regan represents another such case. A judge could theoretically grant the house back to the estate and replace Regan with a new executor. The beneficiaries could also try to sue Regan for damages, something they have been hesitant to do given how much time and money it would likely cost them. Even if they won, there would be no guarantee that Regan would ever pay up. Howcroft doesn’t think they’ll ever find the money. He believes Regan to be “a man of straw.”

But Young is no longer concerned about the money. He’s even made peace with the fact that the estate may lose the house. At this point, he has only two wishes. First, for Sami and June’s adventure to end the way they intended: with their ashes buried side by side with their cats. And second, for no one else to have to go through what the five beneficiaries have endured. It’s not just a theoretical concern. “I’ve drafted a lot of wills in my time,” Regan once told the beneficiaries. “Probably 20 per cent of them, I’ve been asked to be an executor.” Which means that, at any point, Regan could get a call asking him whether he’d like to handle another estate.

This story appears in the June 2026 issue of Toronto Life magazine. To subscribe, click here. To purchase single issues, click here.