For 40 years, the wealthy Kamin family relied on Sheldon Carr for everything. He was their money manager, their fixer, their friend. But after the 99-year-old matriarch died, her kids accused Carr of betraying their trust and taking millions of dollars

One night in 1952, Jack Kamin struck a deal that would make him rich. Back then, he owned an electrical company that supplied lighting to the TTC. But what he really wanted was a stake in the real estate business. The war was over, the baby boom was at its peak, and the market was explo­ding. That night at dinner, Jack and two friends, Eph Diamond and Joe Berman, shook on a plan to launch a construction company. Jack would invest $40,000 of his own money, he’d lend Eph $40,000 as his investment share, and Joe would chip in $20,000. After they paid the cheque, they climbed into Jack’s 1951 Cadillac, parked outside. They took one look at the car and decided to name the company after it.

Over time, Cadillac grew into one of Toronto’s biggest developers, snapping up land all over southern Ontario. Jack eventually sold his stake, but he continued buying up massive swaths of land across the GTA. He held onto the parcels for years, sometimes decades, partnering with developers and amassing an enormous fortune. After he left ­Cadillac, it went on to merge with Fairview, the Bronfman family’s real estate giant. The resulting company, Cadillac Fairview, would be responsible for much of Toronto’s glassy skyline, including Mies van der Rohe’s TD towers, the Eaton Centre and Simcoe Place.

Jack was a slim man, with tawny skin, droopy eyes and a long, striking nose. In his younger days, he looked a little like Humphrey Bogart, and he had some of the Bogie panache, too, with a keen business sense, a strong bullshit detector and a vast imagination. When he first met someone, he would often ask the same questions several times, rapid-fire and in different ways, to test their sincerity. He lived for work and often showed up to his country club pool wearing a suit.

The only thing Jack loved more than business was his wife. Her name was Syra, but everyone called her Buschie. They’d grown up together as family friends, though the relationship stayed platonic until Jack heard that someone else was courting her. He wouldn’t have it. One night, he showed up on her doorstep with a diamond ring and proposed. They were married in December 1940 at the McCaul Street Synagogue. Syra wore a silver lamé Queen Anne headdress, and a floor-length gown with a sweetheart neckline and dramatic train. The Toronto Star ran her portrait in the society pages the following week.

The couple’s first child, Michael, was born in 1944, followed by his sister, Ruth, six years later. In 1950, the family bought a stately yellow-brick mansion on Ridge Hill Drive in Forest Hill, where Syra hosted ladies’ luncheons for the Hadassah women’s group, and played mah-jong and canasta. Despite their wealth, Jack and Syra were notorious penny-pinchers. The family often joked about how the wallpaper was peeling off the walls of her West Palm Beach condo, but Syra refused to get it fixed because she didn’t want to spend the money. Jack sent the kids to Forest Hill Collegiate instead of private school. When Ruth turned 16, he gave her a lump sum clothing allowance for the year, and she had to make it last. He was determined to teach his kids the value of a dollar.

In 1972, Jack Kamin met Sheldon Carr, a 28-year-old accounting student at Laventhol and Horwath, the firm that handled Jack’s business. Carr grew up in Toronto’s west end, where he attended Parkdale Collegiate. He was diminutive and slight, with narrow eyes, a broad smile and thick hair that crested like a wave atop his head. Jack took a liking to the serious, soft-spoken young man. When Carr joined the firm as a chartered accountant, he took on more and more of Jack’s business dealings, eventually managing accounts that were worth millions. A few years later, he made partner.

Jack had a turbulent relationship with his son, Michael. Carr has said that the younger Kamin wasn’t particularly interested in his father’s business and lacked personal ambition. In Carr, Jack found a surrogate son: a young man who possessed a tireless work ethic, strong family values and a desire to succeed. Carr’s own father had died when he was young, and he was happy to adopt Jack as a proxy. He managed Jack’s finances, but also served as a trusted confidant and friend, eager to accompany his mentor to meetings and watch him broker deals.

As Jack got older, he realized he needed to appoint someone to protect the Kamin legacy—someone methodical and reliable, who would act in the family’s best interest. He was certain that person was Sheldon Carr. By the mid-1980s, he’d given Carr signing authority over the majority of his empire.

Canada’s plutocrats are an elite group, and the people who keep them rich—the army of accountants, wealth managers, investment bankers—are almost as powerful. It’s not unusual for accountants to keep separate offices just to manage the affairs of a single wealthy family. Families living off estates have to calibrate a balance between risk and protection. They also have to hire the right people.

The Kamin accounts made up some 15 per cent of Carr’s practice. He also oversaw the $75-million estate of the real estate magnate John Kaptyn, as well as the accounts of long-time Speaker of the House of Commons Gilbert Parent. Carr was an expert at keeping his clients happy. He became known as serious and diligent, a fastidious micromanager. He could also be ruthless. Once, he poached two accountants from a partner’s team, allegedly in an attempt to force that partner out of the firm. It worked.

Carr and his second wife, Bonni, had a blended family of five kids. They lived in a small bungalow at Bayview and Sheppard. He drove a green Jaguar in the summertime and a beat-up Hyundai Tucson in winter. (His daughter liked the beater so much that he eventually gave it to her.) In the evenings, Bonni would read and knit while Sheldon would unwind in their basement sauna. Friends say the marriage was loving. “We should all have partners who are as devoted to us as he is to her,” one told me.

Carr was always impeccably dressed, but he was less flamboyant than some of his Bay Street colleagues. He didn’t drink much or hit the party circuit, choosing instead to spend summer weekends playing golf or boating on Lake Simcoe with his wife and children. He was generous with his time, mentoring several young accountants who would go on to have prominent careers, and working for years as the president of the Associated Hebrew Schools of Toronto, one of the ­biggest private day schools in North America. He served on the board of governors of Mount Sinai Hospital, and donated to Prostate Cancer Canada, the Princess Margaret Cancer Foundation and Community Living Toronto.

Over the years, Sheldon and Bonni grew close to Jack and Syra. The couples would go out for dinner together, and the Carrs attended the Kamin kids’ weddings. Syra was as fond of Carr as her husband was, and she too treated him like a member of the family. But for Carr, the Kamins were always clients first, friends second. He understood that it was in his best interest to keep his clients on his books for decades, using whatever means ­necessary. Through a mix of hard work, camaraderie and charm, he cultivated a relationship that would make his career. Over time, he came to know more about the Kamins’ finances than their own adult children did. “For many, many years, that family wouldn’t go to the bathroom without calling him,” says one long-time colleague.

In 1993, at age 77, Jack Kamin developed a fever. He was admitted to Sunnybrook Hospital and went into organ failure. A few days later, he died. After the loss of their patriarch, the family relied even more heavily on Carr—for financial matters, for personal support, for just about everything. At 78, Syra had never so much as paid a phone bill. She had a high school education and, though she read the newspaper daily, she knew little about money except that she should save it. When she needed cash, she phoned her surrogate son, whom she affectionately called Shelly. He paid her bills, filed her taxes and reviewed her bank statements, which were mailed directly to his office. He wrote the $100 anniversary cheques she gave to her kids and grandkids each year. He interviewed and hired her live-in caregiver. Syra also named him director of Syra Kamin Ltd., or SKL, the ­multimillion-dollar corporation Jack had set up and managed for her, and granted him full signing authority.

Meanwhile, Carr’s career was rising steadily. He ran his own firm, DMCT LLP, which later merged with the accounting behemoth Collins Barrow. Like the Big Four—Deloitte, PwC, EY and KPMG—Collins Barrow is a network of independent Canadian firms linked together under one umbrella. Collins Barrow Toronto eventually acquired the Bay Street firm Smith Nixon, and the deal paid off. The company’s stature grew, and revenues along with it. While the rest of the DMCT offices moved down to the Financial District after the merger, Carr kept an office on Eglinton. It was just for the Kamin accounts.

By this point, he was managing personal taxes and investments for the Kamin children and grandchildren. Ruth was on her second husband, and she had a son from her previous marriage. Michael and his wife had three children of their own. Carr saw to the Kamins’ day-to-day affairs, and they went to him with their own business concerns when they had them. Carr hired a dedicated bookkeeper to help him keep up with the extra work—paid for by Syra Kamin, of course.

In 2007, Carr’s investment adviser, Bobbi Benson, left her job at BMO and started working at RBC. Carr transferred all of his personal trading accounts there, and he encouraged Syra to do the same with the Kamin accounts. The accounts were self-directed, which meant all trading decisions were made by the account holder—in this case, Sheldon Carr—instead of the bank.

By his own admission, Carr was an unsophisticated trader, but he still had full authority to trade on Syra’s accounts. Secretly, he’d developed a predilection for bullish, compulsive investing, putting his and Syra’s money into high-yield, high-risk stocks like IPOs and Chinese tech companies. Eventually, he opened margin accounts with RBC in his own name, which enabled him to borrow against the bank to make trades. Many margin account holders end up wildly in debt, and some accountants in Canada think they should be illegal.

According to the Kamin family, Carr and Benson made a crucial and deliberate error on Syra’s file: they listed her investment knowledge as “sophisticated” and claimed she was looking to place 50 per cent of her RBC portfolio in medium- to high-risk investments. This would allow Carr’s high-risk trading to continue to go unnoticed by RBC senior management.

Benson says Carr was calling her several times a day for years, ordering her to make extravagant trades in penny stocks and incurring major losses. By day, he was the steady hand, guiding his clients wisely through their financial planning. By night, he was gambling away his own nest egg.

In the mid-2000s, Syra Kamin’s fortune reportedly amounted to some $200 million, mostly tied up in real estate and investments. She was in her 90s at this point, and her health was beginning to falter. She suffered from spinal stenosis, which left her increasingly housebound. Sheldon Carr regularly visited her condo on Heath Street, where she’d moved after selling the family home in Forest Hill. He’d bring her documents, and stay for a cup of coffee and a chat. On two occasions, first in 2009 and then in 2010, he stopped by with some documents. Syra signed them in her brittle, shaky handwriting.

The documents were guarantees, which put the contents of her RBC investment accounts up as collateral against any investments made from Carr’s personal trading accounts. And they would form the basis of a multimillion-dollar legal battle between Carr and the Kamin family. The Kamin kids say Syra had no idea what she was signing. However, a representative from RBC spoke to her at the time and reported that she understood clearly.

As Syra grew older and more fragile, her son, Michael, began to doubt her mental acuity. He thought his mother’s health had deteriorated to the point where she could no longer make informed financial decisions, and he launched a formal challenge to test her mental state. When she was declared fully competent, she filed an addendum to her will. Michael was largely disinherited and removed as an estate trustee. In the last six months of her life, she was forgetting names and dates, though she always remembered her children, and she always remembered Shelly Carr.

In 2014, just after Thanksgiving, Syra Kamin died of a stroke at age 99. Her affairs were in good order. Her will stipulated that Ruth would receive half of the estate. She would also get a trove of jewellery, including a diamond brooch, a platinum 4.75-carat diamond ring, a platinum bracelet dotted with 190 diamonds and a Lalique jewellery box.

Because Syra had mostly cut Michael from her will, he would receive only earnings from his half-share, and the residuals would go to his heirs after he died. She also bequeathed him a gold marquis diamond ring, plus an extra $75,000, since Ruth got most of the gems. Syra’s granddaughter would get her gold and tiger’s eye Bueche-Girod watch, along with her furniture and artwork. Each of her four grandchildren would also receive $1.25 million, and her son- and daughter-in-law would each get $50,000. Her seven great-grandchildren were entitled to $75,000 each. Her caregiver, hired by Carr, would receive $25,000. Finally, she appointed three trustees to manage and distribute the estate: her daughter, Ruth; Michael’s son Paul; and Sheldon Carr, who could act as a mediator in case of a family disagreement.

The family held a funeral and buried Syra next to her husband, under a headstone etched with her nickname, Buschie. After the service, friends and family members gathered at Ruth’s home to sit shiva. Sheldon and Bonni Carr were there. Bobbi Benson sent a note of ­condolence.

In the months after Syra’s death, the three trustees met to discuss the ­distribution of the estate. According to Bobbi Benson, their investment adviser, the estate was worth some $200 million. The Kamins claim that this figure is exaggerated, but won’t provide their own number.

Paul and Ruth agreed that Carr should manage the particulars. It seemed only natural. They didn’t know much about the family finances, while he understood the intricacies better than anyone. Ruth and Paul retained signing authority, and Ruth would often stop by Carr’s office to sign cheques when he asked. But he was also signing cheques and documents on his own. They’d known him forever and trusted him implicitly, so they didn’t bother tracking activity in their accounts. Carr has said that they neglected the estate and shirked their duties as trustees, assuming that, as usual, Shelly would take care of everything.

Though estate trustees are legally obligated to administer in the heirs’ interests, they have huge financial leeway. In some cases, they’re permitted to invest or sell assets, hire employees and buy property. Unless the will states otherwise, they don’t need to clear those decisions with anyone except their co-trustees. Often, they can even create corporations on behalf of an estate, or buy assets from an estate for themselves, provided it’s all done in good faith. As such, selecting a trustee requires an enormous amount of, well, trust. There’s no official vetting process: any Canadian over the age of 18 can act as a trustee on an estate, regardless of their financial or legal expertise. Of course, given the workload, there are obvious benefits to choosing someone responsible and reliable, plus someone with the tact to handle potentially explosive family conflicts. It’s a remarkably informal selection process for what can be a years-long job. As payment, they might earn up to five per cent of the value of the estate.

By late 2014, Carr’s personal investment accounts were millions of dollars in the red. He was quietly panicking. Two months after Syra died, Benson told him that RBC intended to make a demand on the guarantees to cover his personal debts. He decided to transfer the money from the Kamin accounts to cover the overdrafts. On December 22, 2014, he authorized a transfer of $3.4 million into his personal trading accounts. He figured he’d make up the difference before anyone noticed the money was gone.

The Kamin family has never wanted for anything. Ruth lives in a stone mansion in Forest Hill, and Michael spends half his time in his York Mills condo and the other half in West Palm Beach. Syra used to say her children had been retired since the day they were born. They celebrate birthdays together and gather at Ruth’s house in Forest Hill for Jewish holidays. They fly south to Florida for the winter, or to Arizona. They’ve always had so much money in the bank that they never had to worry—until a chunk of it disappeared.

In December 2015, 14 months after Syra’s death, RBC sent a letter to the three trustees asking them to come in to discuss the goals of the estate. The regional director for RBC’s securities branch, Gary MacDonald, wanted to know what their investment objectives and risk tolerances were, to review the estate’s current investments, and to learn who, exactly, they should be taking instructions from on the hefty accounts. None of the trustees responded to the meeting request. Carr told Ruth and Paul he would handle it. He didn’t.

By early 2016, only $1.4 million of the payouts from Syra’s estate had been issued. Michael’s other son, Marc, a lawyer in Arizona, began to ask Carr when his share would be paid. Carr replied that there wasn’t enough cash in the estate to pay him out until at least the end of the year. “I can’t imagine there is not $750K in cash available,” Marc wrote back. Carr explained that since so much of the estate was tied up in real estate holdings, some of those assets would need to be sold to free up the money. His excuses kept mounting. He’d been out of the office because of illness, he said. He’d been on vacation for a week. He would promise to send detailed financial statements, then never would. Over the course of the winter, emails flew back and forth between Carr and the Kamins. They were growing suspicious.

In February, Paul Kamin visited RBC’s Bay Street offices. He sat in a state of shock as he learned that after his grandmother’s death, Carr had transferred $3.4 ­million into his personal accounts. He discovered that there was far less cash in the estate accounts than the family had been led to believe. And he learned that Carr had managed to sign one of the guarantees as both the beneficiary and the guarantor, because he had signing auth­ority for Syra. Paul called Ruth and asked her to meet him later that evening at his north Toronto home. This wasn’t the kind of information he should deliver over the phone.

Ruth was too stunned to cry when she heard the news, betrayal running through her body like a current. How had this man set up a scenario that allowed him to pull the puppet strings at every turn? She couldn’t believe it. She didn’t want to believe it. She desperately hoped it wasn’t true. The Kamins tried to keep their anger in check and emailed Carr to set up a meeting. They wanted to give him a chance to explain, to honour the history between their families. There had to be more to the story.

Two weeks later, the three trustees met in a boardroom at Collins Barrow’s King Street office. Carr was surprisingly calm, collected, even blasé. The Kamins posed question after question but made sure not to accuse him of anything. They wanted to watch his behaviour, to give him the chance to come clean. In the end, he agreed that he wouldn’t stickhandle the estate going forward.

Days later, he tried to sell off more than 100,000 of the Kamins’ shares in Facebook, Twitter, Visa, GlaxoSmithKline and other companies, presumably to fix the cash-flow problem he’d been hiding. This time, an RBC investor flagged the attempted sale. The Kamins were furious. They filed to have Carr removed as a trustee, which would revoke his ability to touch any of the family money.

Over the next two months, the trustees, their lawyers and their accountants waded through rafts of incomplete financial information relating to Syra’s estate. They discovered accounts at TD and Travelers Canada, plus State of Israel bonds, all in Syra’s name, and all left off the records that Carr had prepared. The man their father had so deeply trusted, the man who had handled the family fortune for more than 30 years, the man who had attended their weddings and sat shiva for their mother, had betrayed them.

In May 2016, Collins Barrow discovered Carr’s conflict with the Kamins and requested his resignation. Clients went ballistic. Though Carr, now in his 70s, was no longer handling many accounts, he was still a ­founding partner. He’d had a decades-long, rock-solid reputation as a gentle accountant who erred on the side of conservatism when it came to his clients’ finances—a portrait completely at odds with what the Kamins say he did.

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When the family filed to have Carr pay back the missing $3.4 million, he filed a response that outlined his assets. He had two retirement funds totalling $225,084, State of Israel savings bonds worth $17,500, and a joint chequing account with Bonni that had $73,000 in it. He had a pension from ­Collins Barrow worth $900,000, and $125,000 in a capital account, which he hadn’t yet received. And he had five RBC securities accounts with a cumulative balance of negative $1.3 million. Even if he had transferred that $3.4 million, he couldn’t pay it back. He didn’t have the money. When they later filed to have him declared bankrupt, he objected. He said he owed the family nothing.

Over the next year, the Kamins expanded their investigation beyond their mother’s RBC accounts. It turned out that ­Sheldon and Bonni had purchased their house using $350,000 they borrowed from Syra. Ruth knew about it before her mother’s death, but Carr had told her he’d repaid it in full. He never did. Three years later, as a signatory of SKL, he forgave the loan to himself—legally and with Syra’s approval, he claims.

The family also alleges that, while he was acting for the family on a development for the Kamin group accounts, he collected a secret $105,000 commission that he transferred to a personal holding company. Other records indicate that when Syra was 96, Carr had arranged for a $10-million life insurance policy for her from a Cayman Islands–based insurer for estate tax purposes. The Kamins believe he collected a commission from that deal, too. (For his part, Carr denies that there were any secret commissions.)

The family says there’s no way Syra knew about the risks involved in any of these decisions. She knew nothing about the securities market. She didn’t understand financial statements and had no idea what a brokerage statement was. She was rich, sick and vulnerable. And yet according to Bobbi Benson, it makes sense for a family worth $200 million to invest in high-risk stocks using a few select accounts. Since she wasn’t investing the whole family fortune, the level of risk was manageable.

In December of 2017, Ruth and Paul filed a blockbuster lawsuit against Sheldon Carr, Bobbi Benson, RBC and others, alleging negligence, unjust enrichment and breach of trust. They claim that Carr spent years mismanaging Syra’s affairs, hoodwinking a bedridden woman out of millions and breaching his fiduciary duty to the family that helped build his career, all the while billing the Kamins $450 per hour on the side for investment advice. They’re seeking $25 million in damages for the money they say he mis­appropriated or traded away, plus another $10 million in punitive damages. No criminal charges have been laid or, for that matter, sought. For the Kamins, justice comes in the form of a cheque. “We want the estate to be made whole,” one family member told me.

Carr declined to speak to Toronto Life, but in his statement of defence he admits that his trading got out of control, and that margin accounts made it possible for him to lose millions in the time it takes to blink an eye. He was grappling with a gambling addiction, he says, while Benson was making off with the hefty commissions. He claims she never suggested to him that his debt was becoming quicksand. He says it led to paralyzing anxiety and depression, which further impeded his ability to recover the losses.

As for the Kamin funds, he says, they were never mis­appropriated because he never withdrew the money. Benson instructed him to authorize the transfer based on the guarantees that Syra signed. The Kamins still insist she didn’t understand them, but Benson says that she was fully aware of their contents and signed them for Carr as a gesture of gratitude for everything he’d done for her.

None of the allegations have been proven in court, and all of the parties involved have denied any liability. Instead, they’re frantically pointing the finger at one another. According to RBC and Bobbi Benson, the blame lies squarely with ­Sheldon Carr. Benson says she was just doing her job, that despite his claims to the contrary, Carr was an informed and sophisticated trader, and his clients trusted him to act in good faith. RBC argues that, because the Kamins gave Carr complete control of the funds, and their advisers took orders from him, they have no liability. They also suggest that some fault lies with the Kamin children handing over control of a multimillion-dollar estate, for not paying more attention as their accountant went rogue. If there are losses, they say, Paul and Ruth must shoulder part of the blame.

The last few years have been cruel to Sheldon Carr. He’s in his 70s, and has received treatment for high blood pressure and prostate trouble. He’s having heart problems that his doctors can’t diagnose. Carr isn’t returning phone calls, not mine or those from many of his friends. One source says he is working shifts in a factory to cover his mounting bills. He and Bonni are separated, and neither of them occupies the North York bungalow where they once lived happily. The front lawn is overgrown.

Jack and Syra Kamin are buried at Beth Tzedec Memorial Park near Bathurst and Finch, the same cemetery where Carr’s father also rests. When Ruth goes to visit her parents now, she talks to them aloud about the troubled family finances, the lawyers and the lost sleep, the betrayal of trust. Forget rolling over in their graves, she says. “They must be doing somersaults.”

This story originally appeared in the September 2018 issue of Toronto Life magazine. To subscribe, for just $29.95 a year, click here.