The other side of Barry Sherman

In the summer of 1988, Barry Sherman received an urgent phone call—from a prison in Oregon. On the other end was a familiar voice: that of Harvey Rubenstein, a notorious Toronto stockbroker convicted of fraud on both sides of the border. Though Rubenstein’s financial scams garnered plenty of headlines, few people had any idea his victims included the founder of Canadian generic drug giant Apotex Inc. Mere weeks before taking that call, Sherman had launched a lawsuit against Rubenstein, his former investment adviser, claiming he’d been duped out of millions.

Now the disgraced broker, recently extradited to the United States to face another slew of fraud charges, was asking for even more of Sherman’s money: US$100,000 so he could post bail. He told Sherman if he weren’t behind bars, he could focus his efforts on recovering his lost money. Sherman agreed. “I couldn’t see any benefit, from my viewpoint, of having him languish in jail,” Sherman later testified in a sworn deposition.

The story didn’t end there. After Rubenstein pleaded guilty, Sherman agreed to loan him half of the $100,000 bail money so he could pay restitution to his victims. But when another creditor stepped forward to claim rights to the remaining $50,000, Sherman spent the next four years fighting in U.S. court to eventually recoup what, for him, was essentially pocket change.

That long-ago tale, excavated from thousands of pages of court documents, corporate records and charity filings reviewed by Maclean’s, reveals the paradoxes of a man whose brutal death is now being investigated by police. A hard-nosed strategic genius who built Canada’s largest pharmaceutical company, Sherman also conducted business with known criminals. He’d generously bail out someone in need—but often with a longer, self-interested view. He was a billionaire driven to litigation less by money than something more primal: a sense of righteous certitude that propelled him to prevail at any cost.

It is now almost four months since the bodies of 75-year-old Sherman and his 70-year-old wife, Honey, were found inside their Toronto house in a horrific, staged tableau: seated side-by-side on the deck of their basement swimming pool, hanging from belts tied to a railing. The violent deaths of one of Canada’s richest couples—their net worth has been estimated at $4.6 billion but is believed to be much higher—rocked the intersecting worlds of business, politics and philanthropy. The Shermans donated millions, notably to hospitals and universities. They were charity royalty, fixtures on the gala circuit, where Honey was beloved.

Their legacy of giving and selfless dedication was the focus of the Shermans’ public funeral in December, attended by more than 6,500 and live-streamed. The country’s business and political elite were out in force, among them Prime Minister Justin Trudeau, Ontario Premier Kathleen Wynne and Toronto Mayor John Tory. Wynne, Tory and Sen. Linda Frum delivered eulogies.

MORE: Jonathon Sherman pays tribute to his parents Barry and Honey Sherman

The ongoing investigation into the Shermans’ deaths now casts a harsher spotlight on their lives as police try to answer why the couple were victims of a “targeted” attack, as was confirmed in January. The mystery deepens as each day passes, with no arrests or known suspects. An affidavit filed in court by a Toronto police officer detailed resources being deployed: 51 officers working the case, combing through more than 2,000 hours of security footage, with “474 investigative actions” being “vigorously pursued,” 240 people interviewed or identified to be interviewed. More warrants and “covert tactics” to track down the killers are expected. A parallel investigation, led by Toronto criminal defence lawyer Brian Greenspan, has been launched by the Shermans’ children, who were angered by reported police leaks that the case could be a murder-suicide.

WATCH: Deaths of Barry & Honey Sherman a double homicide, say police

 

The question to be answered is not only why was Sherman murdered alongside his wife, but why now, at 75? It’s no secret the drug executive had amassed a long list of enemies in his 50-year career. A renowned risk-taker, disruptor and pitbull professionally, Sherman was a polarizing figure—regarded as a softie with a heart of gold by those in his proximity and loathed by those who claim they were outfoxed or betrayed by him. The man who learned weeks before his death of his nomination to the Order of Canada was also called out as unethical in business dealings. The late physician and pharmaceutical entrepreneur Morton Shulman, who did battle with Sherman, called him “the only person I have ever met with no redeeming features whatsoever.”

Sherman’s fortune was built on his canny ability to push systems to their limits—and occasionally beyond, as reflected in a litany of controversies over his political donations, his lobbying and his role in the country’s biggest medical research scandal, a tale helped inspire John le Carré’s novel The Constant Gardener. Sherman, on his own and through his companies, was the country’s most active litigant, a man who used the courts as readily as others use the subway. Even as politicians paid tribute to him after his death, his company was locked in legal battles with their governments on multiple fronts.

MORE: Former CEO of Barry Sherman’s drug company fights back in ‘pillow-talk’ suit

Two decades ago, Sherman himself admitted he could be a target for murder. “For a thousand bucks paid to the right person, you can probably get someone killed. Perhaps I’m surprised that hasn’t happened,” he told author Jeffrey Robinson in the 2001 book Prescription Games: Money, Ego and Power Inside the Pharmaceutical Industry. After that, his list of adversaries only grew, as privately held Apotex expanded into more than 100 countries, including Mexico and India, and began developing a cannabis-based pill. Sherman’s wealth saw him cross paths with high society and low—from business and political elites to shady characters out of a Coen brothers movie. His investments outside of Apotex were both extensive and, at times, perplexing—a list that includes a failed casino bid, a money-losing gold mine, an outfit that produced therapeutic pads for horseshoes, a stake in the hottest commercial real estate venture in the country, a now-bankrupt jewellery company that dealt in “loose diamonds,” an investment in a yacht named The Great Gatsby that never existed and his backing of B movies Real Gangsters! and Sicilian Vampire.

His financial interests, conducted through a web of private companies, trusts and foundations were so Byzantine that even he had trouble keeping them all straight. During his Rubenstein deposition in 1990, a lawyer asked him where he got the bail money. “I don’t know,” he replied. “My banking is very, very complex. I simply instructed my staff to have the money forwarded.”

Sherman’s final months saw him face an array of situations seemingly plucked from spy thrillers. In January, Apotex sued a former employee, alleging he had stolen drug formulations that he planned to use at a factory he was building in Pakistan. Months later, in a lawsuit loaded with salacious details, a key Apotex executive was accused of espionage by the company’s biggest rival. Apotex had been added to a list of generic drug-makers accused of price fixing in the U.S. On a personal front, Sherman was suing yet another known fraudster with whom he’d invested, while his decade-long legal battle with his estranged “orphan cousins” came down in Sherman’s favour in September—then took yet another bizarre turn. Honey, meanwhile, was busy on the charity front and building a showplace new house intended to be the stage for the couple’s next chapter, one that, tragically, would never unfold.

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While studying engineering at the University of Toronto in the early 1960s, Sherman spent his summers driving a delivery truck for Empire Laboratories, a generic-drug distributor owned by his uncle, Louis Winter. It was menial work for a boy genius who went on to earn a Ph.D. in astrophysics from MIT in 1967, but as Sherman later wrote in his unfinished autobiography, those summers would “prove to be of critical importance” to his future. They also provided an early window into the kind of businessman Sherman would become: notoriously bold, ultra-aggressive and in constant pursuit of the slightest angle he could exploit.

Tragically, Winter and his wife, Beverley, died 17 days apart in 1965 (he of an apparent aneurism, she of leukemia), leaving behind four young sons: Paul, Jeffrey, Kerry and Dana. Though enrolled at MIT, and just 22, Sherman told the executors of the estate he wanted to take over as Empire’s general manager for two months—in exchange for $3,000, a car and the right of first refusal on any sale of the company. He demanded an answer within 24 hours or he’d yank his offer off the table.

WATCH: Anne Kingston discusses the unseen side of Barry Sherman on CityNews

The trustees turned down his high-pressure proposal, but Sherman did not give up. After graduating two years later, he once again sought control of his uncle’s company, this time with a partner (friend Joel Ulster) and a formal offer ($450,000). Although the trustees were willing to sell, they wanted protections built into the deal for the Winters’ four sons, since adopted. The most Sherman would agree to was a written option agreement that said his cousins could work for Empire when they turned 21, and buy up to five per cent each of the shares at age 23—as long as Sherman still owned the business. If he sold it, the option would become void. As a judge concluded, years later: “Sherman was asked to be more generous but would not budge.”

The agreement protecting Winter’s sons didn’t survive. A 1969 share swap initiated by Sherman gave control of Empire to its largest customer, and two years after that, the shares were sold for close to $2 million to ICN, a big publicly traded company. Winter’s sons were officially out, and Sherman was poised for his next chapter: Apotex.

Launched in 1974, it was a corporation in constant battle mode: against Big Pharma, against government regulators, against anyone who dared question the founder’s pure intentions. He touted himself as a patent-busting underdog, the courtroom crusader bravely suing the Mercks and Pfizers and Bayers of the world so he could provide needy patients with cheaper generics. “If we’re thieves, we’re Robin Hoods,” he once claimed. Winning in the courts was so crucial to his success that he liked to tell his employees they worked for a legal company that happened to sell medications.

Sherman railed against “incompetent” bureaucrats who had the audacity to disagree with his interpretations of federal drug law—and he dragged them to court, too. In Federal Court alone, Apotex has launched more than 1,200 legal actions, including 83 against Health Canada since 1990. A ministry spokesman says “because of the high volume of cases,” officials can’t even begin to calculate how many millions Sherman’s litigation has cost Canadian taxpayers. Now police must comb through the stacks and stacks of papers that famously lined Sherman’s office.

“He was a disruptor,” says Michele Brill-Edwards, a physician who served as head of drug approvals at Health Canada between 1987 and 1992. “He was the guy who said: ‘I don’t have to play the game the way everyone plays it.’ It was intimidating to come back from lunch and find an urgent memo on your desk saying you’ve got to get over to Federal Court because Sherman was at it again.” His approach with the health regulator, in particular, broke with past practice among drug-makers, who had typically tried to ingratiate themselves. “The sort of gentlemanly way of doing business changed [with Sherman],” says Brill-Edwards. “He quickly demonstrated that in fact you can bully the government and you can intimidate.”

He was certainly willing to play the long game if that’s what it took. One particular spat with Health Canada—a 30-year odyssey over a knock-off of trazodone, an antidepressant—finally came down in Sherman’s favour last April, when the Federal Court of Appeal ruled Ottawa was indeed negligent in its handling of Apotex’s application. “For Barry, it wasn’t about the money,” says Bruce Clark, Apotex’s former senior vice-president of scientific and regulatory affairs. “Money is just how you keep score.”

But his money also provided massive leverage. When necessary, Sherman used his vast wealth and deep connections within the Canadian power grid. When Brian Mulroney’s Conservatives enacted legislation in 1993 that extended drug-patent protection for brand-name medications, bringing to a halt the halcyon days of Canadian generic drug-makers, Sherman ranted about how the new law would kill the industry—and then donated generously to the campaign of Jean Chrétien, whose Liberals promised to review the legislation.

Sherman’s efforts to influence policy didn’t end there, it was later revealed. When Chrétien took office, Apotex had promised the University of Toronto its biggest-ever donation: $20 million toward a proposed $90-million research centre. At Sherman’s request, U of T lobbied the federal government to delay another round of what he considered damaging regulations. Top officials from Mount Sinai Hospital and Humber River Regional Hospital, also recipients of Apotex money, did the same. When their letters failed to sway the government, Sherman withdrew $25 million worth of pledges to various institutions, including U of T. In letters sent out to the institutions, Sherman railed against federal policy that “appears calculated to cause maximum damage to the Canadian generic industry . . . at great cost to Canada’s health care system.” Federal drug policy was unlikely to change, he wrote, “unless we get a new prime minister.”

He tried to do just that in 2006, in a now-infamous, near-absurd example of campaign financing. When Liberal MP Joe Volpe was running for the party leadership, five current and former Apotex executives, as well as 15 of their family members, contributed a total of $108,000—including $5,400 each from 11-year old twins.

More recently, in August 2015, Sherman hosted a cash-for-access fundraiser at his house for Justin Trudeau and a local Liberal candidate, a controversial event that landed the drug magnate in the crosshairs of Ottawa’s lobbying commissioner. The Lobbyists’ Code of Conduct prohibits registered lobbyists (which Sherman was at the time) from placing elected officials in a potential conflict of interest that could make them feel “a sense of obligation.” Before the commissioner could finish her investigation, Sherman dispatched lawyers to Federal Court to try to get the “unanchored fishing expedition” shut down. Never before had someone asked a judge to quash such an active investigation.

But of all his audacious attempts to influence the system, no example made Sherman appear more vindictive—or more exposed his backroom power—than his treatment of Dr. Nancy Olivieri, a respected hematologist at Toronto’s Hospital for Sick Children, in what would become the country’s most shameful medical research scandal. After Mulroney upended patent laws, Apotex turned to developing non-generic drugs; a pilot candidate was deferiprone, a potential treatment for a blood disorder, thalassaemia major. During the trial, Olivieri voiced concern that the drug could cause harm to the children in her trial, and in 1998 she defied a confidentiality agreement to publish her findings. When Apotex threatened legal action against Olivieri—and tried to smear her reputation—the university, which had been promised $20 million from Apotex, took the company’s side.

Olivieri, though ultimately vindicated, spent years fighting to regain her good name (while helping inspire le Carré’s novel). Sherman survived unscathed. The scandal did little to tarnish his stature as a renowned philanthropist, nor did it make politicians think twice about declaring him a “close friend,” as Eric Hoskins, then Ontario’s minister of health, described him after his death. Hoskins later told media he met with the Apotex boss for an hour only 10 days before he died. At the time, the Canadian Generic Pharmaceutical Association was about to sign an agreement in principle with the federal and provincial governments (except Quebec) after 12 months of negotiations, agreeing to vastly reduce the prices of 70 of the most popular generic drugs to avoid the imposition of a price-tendering system. (Hoskins declined an interview request.)

Was Sherman’s murder somehow related to Apotex? As police comb through records, there’s much to decipher. As Maclean’s first reported, Apotex fired—then sued—Mulazim Hussain, a company chemist, 11 months before the murders because Hussain allegedly stole millions of dollars’ worth of drug formulations from two laboratory computers in hopes of building a rival factory in his native Pakistan. Hussain has denied any wrongdoing. Six months later, Apotex was slapped with its own accusations of corporate espionage by the U.S. division of Israel’s Teva Pharmaceutical Industries Ltd., the world’s largest generic drug-maker. In that lawsuit, Teva claims one of its former employees was in a “romantic relationship” with Apotex CEO Jeremy Desai, and leaked proprietary information to her boyfriend. Both Apotex and Desai (who abruptly resigned six weeks after the murders) have filed statements of defence, denying the allegations.

On Halloween in 2017, six weeks before the Shermans were killed, Apotex was also named as a defendant in an ever-widening price-fixing lawsuit launched by a consortium of state attorneys general south of the border. The core allegation is that Apotex “enjoyed ill-gotten gains” by colluding with two other manufacturers to hike the price of Leflunomide, an anti-arthritis drug. The company has yet to file a statement of defence.

And then, of course, there were Winter’s sons, who waged a bitter, decade-long lawsuit for a chunk of Sherman’s pharmaceutical fortune. Now grown, the cousins discovered that long-lost option agreement that was written up to protect their financial interests when Empire was sold in 1967. Simply put, they claim their dad’s company led to Apotex, so they each deserve a five per cent cut. In typical fashion, Sherman fought back with all his might, demanding his cousins return the millions of dollars he gave them after they reunited in the late 1980s. “I did everything I could to help them,” Sherman said during a sworn cross-examination last May, just seven months before he and Honey were killed. “I don’t think anyone else in his right mind would have done for them what I did.”

On Sept. 15, 2017—three months to the day before Sherman and Honey were discovered dead—an Ontario judge sided with Sherman, dismissing the suit as an abuse of process and calling the cousins’ claim “wishful thinking and beyond fanciful.” On Dec. 6, one week before the Shermans were last seen alive, Justice Kenneth Hood issued another ruling, ordering the cousins to pay $300,000 of Sherman’s legal costs.

MORE: Barry Sherman’s legal battle with his cousins goes on weeks after his murder

The timing of those two judgments triggered inevitable suspicions. Could they have been a motive for murder? One of the plaintiffs, Kerry Winter, told CBC’s The Fifth Estate that he’d fantasized about ambushing Sherman at work, slitting his throat and rolling “his head down the parking lot.” He also said, in multiple interviews, that Sherman had asked him years earlier to arrange Honey’s murder. (The Sherman family adamantly denies that claim.)

Speaking to Maclean’s, Kerry insists he had nothing to do with the slayings. “I admit that I have utter disdain and hatred for Barry Sherman,” he says. “He wronged me. He didn’t honour my father. He didn’t honour the option. He pulled a sleaze move. He stopped visiting me. He lied to me. He betrayed me. I have every reason to hate this man, but I had nothing to do with their demise.”

Interestingly, Sherman said something else during his sworn testimony last May: “I don’t have a succession plan.” Despite the company’s insistence that a succession plan had been in place for years, Sherman showed no signs of slowing down in the final weeks of his life. He was the same workaholic everyone knew him to be. “He seemed fine,” says long-time friend Murray Rubin, who visited Sherman in his office a week before the murders. “He told me the [generics] industry was in trouble, but he was always saying there were problems.”

Eric Paul, a long-time business associate and CEO of CannTrust Holdings Inc., the company partnered with Apotex to develop a cannabis-based painkiller pill, saw Sherman at Apotex just days before he was killed. Sherman hit him up for a donation to the Sherman Campus, a recreational and cultural centre in North York made possible by the Shermans’ $50-million gift to the United Jewish Appeal (UJA) of Toronto. “He didn’t say hello,” Paul recalls. “He said, ‘I hear you’re doing well and I’m counting on you for a million bucks for my building fund.’ He had a big smile. I don’t think he had any sense he was at risk.”

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On Dec. 12, 2017, the day before the couple was last seen alive, Honey missed a scheduled meeting at the Baycrest Centre Foundation. Were it any other board member, no one would’ve paid heed, says Josh Cooper, the foundation’s president and CEO. But Honey, a beloved queen bee in the upper echelons of Canadian philanthropy, was known for showing up—or else saying she couldn’t. “It was bizarre,” says Cooper. They sent an email to make sure she was okay. “Honey got back to us right away,” he says. “She said she was dealing with some stuff.”

At the time, no one thought anything more of it. The last weeks of Honey’s life were crammed, as always, with her work on more than a dozen charity boards, among them the UJA, York University Foundation and Friends of Simon Wiesenthal Center for Holocaust Studies. In late November, she flew to Ottawa to receive a “Senate 150th Anniversary Medal” in recognition of her volunteer work, bestowed by her good friend Sen. Frum.

Honey was “the best fundraiser in Toronto,” says Cooper. “It was her full-time job, and she did it well.” She could be aggressive, but “always with a gracious smile that had an ‘ask’ behind it,” says one friend. “It was impossible to say no to Honey,” Toronto Mayor Tory, a family friend, said at the funeral.

Fall 2017 was typically hectic for the couple. In October, they were honoured at the groundbreaking of phase two of the Sherman Campus. Tory sat between them at the 39th Annual Chabad Lubavitch Dinner on Nov. 22. Four nights later, it was a Jewish National Fund event.

The Shermans gave both time and money, says Steven Shulman, campaign director and general counsel for the UJA of Toronto. Honey, never afraid to shake things up, led the charge. Shulman last saw her 10 days before her death—at a meeting she’d convened at the UJA to discuss how to generate more giving from a certain profession, one he declines to name. “You would always see Honey without Barry, but if you saw Barry he was pretty much always with Honey,” says Cooper.

Married for 47 years, the couple was a study in contrasts: “night and day,” one friend says. Honey was a social animal: extroverted, vivacious, with a big laugh. Sherman was the introvert, uninterested in small talk. “When I spoke to Barry it was on an intellectual level, about ideas and what we were trying to accomplish,” says Avrum Rosenzweig, founder of Ve’ahavta, a humanitarian charity the Shermans supported. “With Honey there would be a slap on the back and a ‘How are you?’ ”

The couple did share a steely determination born of dislocation in childhood. Sherman’s father died when Sherman was 10. Honey, née Reich, born in an Austrian displaced persons camp, was the child of Holocaust survivors. After earning an arts degree from the University of Toronto and an education degree from the Ontario Institute for Studies in Education, she set her sights on marrying a doctor and volunteered at Mount Sinai Hospital. She was introduced to the 28-year-old Sherman in 1970. He wasn’t an actual medical doctor but used the “Dr.” bestowed by his Ph.D. They were married by a judge a year later; four children followed.

Honey was known for her candour—and occasional bluntness. In 1993, as chair of the publicity committee of the Canadian Breast Cancer Foundation, she spoke out about unnecessary mastectomies: “We have to take responsibility for our own life because we can’t count on the medical profession,” she told the Toronto Star. Of her own health challenges—severe arthritis, throat cancer, a hip and knee replacement—Honey never complained, says a friend. When she did gripe, it was in a half-joking way about her husband’s work schedule: seven days a week, 10 to eight.

Publicly, the Shermans operated as a formidable team. Honey skilfully organized the home front—family vacations, holiday dinners—while her husband focused on the business. In one Toronto Sun interview, Honey joked that her title at Apotex was “persona non grata.” In truth, she was the company’s best ambassador. As her husband waged war with critics and enemies, Honey forged alliances among the powerful who populate the non-profit sector, using her charm and determination to help others.

The couple also stood united in their support for the state of Israel, though their attitudes to religion differed. Sherman, a self-described atheist, wrote in his autobiography: “I have always felt disdain for organized religion,” and also that “life has no meaning or purpose.” Honey was more rooted in ritual and tradition, says Eli Rubenstein, the religious leader of Toronto Congregation Habonim, who officiated at the couples’ funeral. The couple did so much good for so many people, Rubenstein says. “We don’t even know the half of it.” Honey was on the way to membership in his synagogue, founded by Holocaust survivors, he reports.

Like many long-married couples, the Shermans had their own routines. Just before her death, Honey was planning a four-week trip to Miami, where the couple owned a condo, to begin Dec. 18. Her husband was to join her on the 25th, but unlike Honey, he wouldn’t be hitting the links. “Work was more important to him than sitting in Florida,” says Paul, the CannTrust CEO. “He didn’t hit a ball.”

Where her husband could be frugal to the point of ostentation, Honey, herself known to fly economy, enjoyed a few upper-middle-class trappings: nice jewellery, a Lexus SUV, getaways with “the girls,” shopping in New York with her sister, Mary. At their funeral, long-time Apotex executive Jack Kay recalled Honey and Sherman visiting his house in the early days of Apotex. Taken aback when she saw a swimming pool, Honey called out her husband for telling her they couldn’t afford one. The differences were showcased at a 50th birthday party Honey threw for Sherman. Guests were guided outside to see a new sports car with a big red bow. “Barry was not happy with the gift,” says Rubin. “ ‘Take it back,’ he told Honey.” She did.

In the last months of 2017, Honey’s time was also focused on the construction of a grand new house; the move would see a couple known for their relatively low-key lifestyle upsizing at an age most people are doing the opposite. Honey purchased a prime corner property, held in her name, in the city’s exclusive Forest Hill neighbourhood in November 2016. (The purchase price is not disclosed in land registry documents.) The intent was to demolish the existing house and build a stunning structure. Architectural drawings filed with the city reveal a 16,000-sq.-foot brick-and-stone home with a separate pool house, a 41-foot retractable skylight over a central swimming pool, an event room, an elevator and a space for live-in staff. Sherman’s need for privacy was reflected in the “large shredder” planned for an upstairs office.

The ambitious plans called for 15 variances in the building code, some sizable, including increasing the maximum building depth to 47.6 m from the allowable 19 m, and a car stacker in the three-car garage. All the variances were approved on June 28, less than six months before the murders.

The move would see the couple leave the six-bedroom, nine-bathroom North York house they’d called home since 1991; they’d moved in after five years of construction. When they discovered the work did not meet their standards, they launched more than a dozen lawsuits against architects, contractors and tennis-court designers. At one point, Sherman testified that the house was a “disaster.” At the core of the dispute was an allegedly faulty garage structure with a tennis court on top and a sauna and underground pool inside—the location where the Shermans’ bodies would be found. By the time the court battles were resolved, the couple recouped close to $2 million of the estimated $2.3-million construction costs.

Sherman wasn’t keen on moving from the house on Old Colony Road, but was doing it for Honey. “He just said: ‘You know, I wish I was staying here, but my wife wants to move so we’re moving,’ ” says Frank D’Angelo, Sherman’s close friend and business partner in non-Apotex ventures.

On Nov. 27, their house was listed for $6.9 million, described as an “architectural modern masterpiece.” Why the Shermans were selling when contractors hadn’t begun to build their new home isn’t clear. What is certain is that listing meant disruptions and privacy incursions—and a lockbox on the house, a rarity for such a high-end property.

Planning the house brought Honey to Apotex on Dec. 13, a day after she missed the Baycrest meeting. It was the last time the couple was seen alive. They were meeting with the builder to go over some design changes, Greenspan tells Maclean’s. Everything was going as planned. Or so it appeared.

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When the Shermans put their house on the market, they did what many rich people do to protect privacy: they used a numbered company as the seller. Sherman had a library to choose from; the one that was chosen listed him as president and his sister-in-law, Mary Shechtman, as a director.

That Sherman had a numbered Ontario company with his sister-in-law named as an officer wouldn’t surprise anyone familiar with his labyrinthine holdings outside of Apotex—ventures that put the test to Sherman’s claim he didn’t care about making money. Relatives pop up in the records of Sherman’s non-Apotex ventures held through “Sherm”-prefixed companies—including Shermco Inc., Sherfam Inc., Sherfam Industries Inc., Sherfam Holdings Inc.—as well as Bernard C. Sherman Limited and numerous trusts and private foundations. The Shermans’ real estate holdings—apartment buildings, condos, commercial properties, rumoured private islands—were held via Sherfam Inc., Signet Realty and Weston, Fla.-based Sherm Realty, as well as trusts. At one point, Sherman owned Deerhurst Inn, an Ontario resort, but sold it after failing to obtain a casino licence. Just months before he was killed, he partnered with a prominent Toronto developer to provide $61.5 million in financing for the most buzzed-about condominium project in the country: The One, an 85-storey structure to be built at the corner of Yonge and Bloor.

Many of Sherman’s non-Apotex ventures were coordinated within his company and listed the same address as his drug-maker: 150 Signet Dr. So it’s unsurprising that Apotex is where Sherman’s friend Myron Gottlieb showed up on Aug. 15, 2015. He went there to meet with company executives to vouch for Shaun Rootenberg, a convicted fraudster looking for Sherman to invest in an app he was developing, Trivia for Good. According to court documents, Gottlieb met Rootenberg (a.k.a. Shaun Rothberg) in prison when he himself was incarcerated for fraud related to Livent Inc., the theatre company he co-founded with Garth Drabinsky. Sherman would ultimately invest $150,000, at Gottlieb’s urging, but would later sue Rootenberg, alleging he and others defrauded him. (Gottlieb is not named in the suit.)

Sherman trusted his gut and was willing to take risks, says Paul, who met Sherman 27 years ago when he approached him with a pharmaceutical-related venture. He was surprised at how quickly Sherman signed on. “Barry liked the story and said, ‘Let’s do it,’ ” Paul recalls. “Usually, people say: ‘Send the financials and we’ll do an analysis.’ ”

Such willingness made Sherman a target for people down on their luck or shilling a deal, says Paul: “He was well known in the community, so anyone who had a need—say a business going sideways—would go talk to Barry. Nine times out of 10 he would loan them or give them money.”

Shashank Upadhye, who worked as Apotex’s chief counsel from 2007 to 2012, heard many stories about Sherman’s quiet charity, whether it was covering someone’s tuition or helping an employee pay for a parent’s medical bills. “He was a real generous guy,” Upadhye says. “Now, anecdotally, I do know there probably were some people who took advantage of him, especially in business ventures, people he thought were his friends.”

Paul says he was familiar with the inner workings of these deals, and some left him aghast: “He was giving people money when there was no opportunity for success.”

Sherman, being Sherman, was often aggressive in seeking restitution. In the 1980s, he was one of many high-profile Canadians burned in what’s considered the biggest tax fraud in the country’s history—limited-partnership tax shelters involving luxury yachts Elegance and The Great Gatsby. When it was revealed that no yachts existed, Sherman tried, unsuccessfully, to sue his accountants for negligence, claiming he lost more than $600,000. The Ontario Court of Appeal said Sherman was an “astute businessman” and “experienced investor” who should have known better.

His investments could also land him in conflict with regulators and the law. Sherman clashed with the U.S. Securities and Exchange Commission in 1994 over failing to disclose his ownership of Kinesis Inc., a now-defunct Nevada-based company that made therapeutic pads for horseshoes. Sherman told authorities he was a passive investor and that he’d been given options that upped his ownership stake without his knowledge. The SEC issued a warning.

A year later, Sherman had a run-in with the FBI and the U.S. Food and Drug Administration over a mail-order scheme he ran with his brother-in-law, Allen Shechtman. It involved a Bahamas-based company, Medicine Club, mailing Apotex drugs, including generic Prozac, from Canada to half a million U.S. households without prescription. Medicine Club pleaded guilty to one count of illegal interstate commerce and was fined US$500,000 for selling drugs without approval; it was also forced to pay $339,000 for investigative costs. Authorities had been tipped off by U.S. drug manufacturers, entrenched Sherman foes. (Sherman bankrolled another of his brother-in-law’s ventures, Martin Ross Group Inc., a jewellery company that filed for bankruptcy in 2015, owing $5.2 million to two Sherman-controlled companies.)

MORE: The Barry and Honey Sherman murder investigation by the numbers

Questions about Sherman’s investments would also cast a light on the management of his private charitable foundations: the Apotex Foundation, founded in 1984, and the Sherman Foundation, founded in 1999. Honey, the public face of the couple’s giving, was not a director of either; both were managed by Sherman, Kay and long-time Apotex executive Paul Buxton. Nor was Honey a director on the smaller Sherman Family Foundation, founded in 2015 and run out of Apotex, with $1.3 million in total assets at year-end 2017. It was run by her husband, their eldest daughter, Lauren, and Apotex’s VP of finance Alex Glasenberg.

In 1996, Sherman sold to the Apotex Foundation half his stake in the scandal-plagued Nutrition for Life International Inc., a Houston-based supplement marketer. He cleared US$6.7 million. Once again, Sherman was linked to a convicted criminal, in this case Nutrition for Life’s owner, Kevin Trudeau, who pleaded guilty to cheque and credit card fraud. Sherman, who bought the stock in the 1980s, had extended a US$650,000 loan to Trudeau. The stock price plunged in early 1996 when Trudeau’s convictions became public, and again on news that Trudeau and the company paid fines to settle U.S. charges that they were running an illegal pyramid scheme.

Selling to the foundation, rather than in the market, was a simple stock-for-money swap, Sherman told the Globe and Mail in 1997, calling the stock “a good asset.” He trumpeted his good intentions. “I sure hope you’re not making me look like some kind of sinister character because, you know, I believe I’m doing all the right things,” he said. “Trying to build an industry, build a foundation, do all the right things for Canada.”

Over the years, Sherman’s foundations also took near-unprecedented advantage of a provision in the Tax Act that allows people running private foundations to donate cash to the foundation, receive a tax credit, then retain the use of that money by having the foundation lend it back to their business. At the time of the Shermans’ deaths, both the Apotex Foundation and the Sherman Foundation had 99 per cent of their assets—some $240 million, an all-time high—loaned out to Sherfam Inc., the holding company that controls Apotex, according to the foundations’ audited filings to Canada Revenue Agency (CRA).

For private foundations to loan out money to this extent is highly unusual. Of the more than 5,000 private foundations that filed taxes with the CRA for 2016, only 322 reported assets as “amounts receivable from non-arm’s-length persons.” Of those that did, Apotex Foundation ranked first and second in terms of percentage of assets extended as loans among foundations with assets of over $6 million. Kate Bahen, managing director of watchdog group Charity Intelligence, expresses outrage at the practice and says the law should be changed. “I have never seen anything like it before,” she says. “Barry Sherman was using his foundations as a piggy bank.”

An Apotex spokesman refused to comment “on the management of a private foundation which operates within the law and is solely dedicated to helping people and organizations in need.” Even in doing good, Sherman pushed limits to the max.

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On a recent afternoon, a lone workman at Honey’s Forest Hill property finished filling in a foundation three-quarters dug out. The ambitious project is now a field of dirt. Building permits remain on the fence surrounding the lot; one sign reads: “Danger  _______,” the unfilled blank a reminder of the murder mystery yet to be solved.

The stakes are high—for the police and for the people, charities and businesses tied to the Shermans. A protective circling of wagons, and emphasis on the couple’s legacy of giving, were evident at their public funeral. “We didn’t want to focus on the manner in which they passed away,” says Rubenstein, who officiated at the service. “First, we didn’t know what happened, but second, that isn’t their legacy. Their legacy is the goodness and kindness they shared.”

MORE: What’s slowing the cops down at Apotex headquarters

Major charities that the Shermans supported, among them the UJA, had a hand in planning the funeral with the family. There was talk of holding the service at Roy Thomson Hall or Massey Hall, but it was decided that a cavernous convention centre, close to the airport and Apotex headquarters, would be most appropriate. During the service, Jonathon Sherman announced that he and his sisters would establish yet another private foundation to honour their parents’ legacy of philanthropy. The children have also said they plan to raze their childhood home, erasing all remnants of the gruesome crime scene.

Friends and family, understandably, don’t want the Shermans’ horrific deaths to mar the couple’s accomplishments—or to thrust the spotlight on controversy. Yet controversy has been unavoidable. In December, Mayor Tory was criticized for communicating the family’s anger to Toronto police over reported leaks that the force was treating the deaths as a murder-suicide (the police board determined there was nothing improper in Tory’s communication). Upadhye, the former chief counsel at Apotex, says he was relieved when police ruled out the possibility of murder-suicide because that would have damaged Sherman’s legacy. “In my heart, I feel a little better—as perverse as it may sound—that it was foul play,” he says. “I want to believe in my heart it was totally random and senseless as opposed to calculated.”

In January, a newly appointed lobbying commissioner dropped the investigation into Sherman and Apotex’s 2015 fundraiser for Trudeau, a decision now being challenged in court by Democracy Watch, an advocacy group that contends Apotex shouldn’t be let off the hook. Apotex, too, is telegraphing corporate unity, evident in the wave of Apotex-logo blue at the funeral. Thousands of employees wore the colour, including many sporting T-shirts with the message: “We will continue your legacy.” “They asked us to do it,” said one employee, who chose not to give her name to Maclean’s. “It’s the least we could do.” Apotex executives declined to be interviewed for this story.

Paul, whose firm continues to work with Apotex, speaks of the high energy level inside the company, even amid swirling rumours of a sale. “They’re working as a team,” he says. “They don’t have to wait for one person to make a decision.”

One of Sherman’s final decisions, it turned out, involved the fractious lawsuit with his cousins. Unhappy that the judge ordered the brothers to pay him only $300,000 in legal costs (he wanted $984,813.73), Sherman appears to have instructed his lawyers to appeal the ruling. They did, the very morning after his funeral—a move that saw Sherman litigating from the grave.

Now investigators must plumb the often subterranean and impenetrable maze that was the Shermans’ life. Hidden deep within those layers—in a court filing, perhaps, or one of Sherman’s countless investments—could lie the clue that cracks the case. The question is whether their world was so complex that the truth will never be found.

With files from Terra Ciolfe.

Contact the authors here: Anne Kingston and Michael Friscolanti.

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MORE ABOUT BARRY SHERMAN:

• Former CEO of Barry Sherman’s drug company fights back in ‘pillow-talk’ suit
• Barry Sherman’s company says fired employee stole valuable drug secrets
• Barry Sherman’s legal battle with his cousins goes on weeks after his murder
• Judge greenlights lawsuit alleging Barry Sherman’s company stole rival’s trade secrets