The UnsolvedMurderOf An Unusual Billionaire
Last December, a Canadian pharmaceuticals executive and his wife were strangled in their home.
No one knows who did it or why, but everyone has a theory.
The Scene Of The Crime
Last Dec. 15, two real estate agents arrived at a sprawling modern house near the northern edge of Toronto. They were accompanied by a couple who were considering buying the 12,000-square-foot mansion at 50 Old Colony Rd., recently listed for just shy of C$7 million. With five bedrooms, nine bathrooms, a gym, a sauna, a tennis court, and underground parking for six cars, it was one of the more impressive properties on a street lined with grand homes. The sellers, pharmaceuticals billionaire Barry Sherman, 75, and his wife, Honey, 70, had lived there for more than two decades but were preparing to build a house closer to the center of the city.
The Shermans weren’t supposed to be home that day. It was midmorning, and a housekeeper was doing her semiweekly cleaning while another woman watered the plants. The tour took in the hexagonal entrance foyer, with its chandelier and black tile floors, and the spacious kitchen, soaked in natural light from a broad conservatory window over the sink. In the basement, the Shermans’ agent had something more unusual to show off: a lap pool and hot tub, handy in a city where winter weather can drag into April.
The pool was at the rear of the house, adjacent to a sunken garage and accessible from the rest of the basement by a long, narrow hallway. The agent, entering first, was the one who found them. Barry and Honey, spouses of more than 40 years, were side by side on the floor, their necks tied with men’s leather belts to a metal railing, about three and a half feet high, that ran around one end of the pool. Barry, heavyset with a crown of frizzy, thinning gray-and-brown hair, was seated, legs extended forward and crossed neatly at the ankles. Honey, who had a blond bob and an athletic frame, was slumped on her side and appeared to have been struck on her face. Their arms were drawn back, held in place by coats pulled down below their shoulders. Both were facing away from the water and fully clothed, although one of the belts seemed to have been taken from Barry’s trousers. It was impossible to tell how long they’d been dead.
Within hours, the deaths were the biggest story in Canada. Barry Sherman was the chairman of Apotex Inc., a privately held generic drug company that he founded in the mid-1970s. It’s now the country’s premier pharmaceutical manufacturer, accounting for as many as 1 in 5 Canadian prescriptions, and the rare large domestic drugmaker never to have been swallowed up by a foreign rival. With a fortune that the Bloomberg Billionaires Index placed at $3.6 billion at the time of his death, Sherman was Canada’s 18th-richest person, and he and Honey were among the country’s most generous philanthropists, supporting cultural and educational institutions, antipoverty organizations, and, despite Sherman’s avowed atheism, a panoply of Jewish causes.
Canadian high society is a small place, and everyone in it was familiar with the Shermans, not least because of their enthusiastic fundraising for the governing Liberal Party. Prime Minister Justin Trudeau was among about 6,000 mourners at a memorial service held a week after the deaths. During a long procession of eulogies, affectionate recollections mixed with a sort of stunned incomprehension. Who could want to kill two people whose “humanity knew no bounds,” as Toronto Mayor John Tory put it? How could a couple at the peak of society, with all the security and confidence that great wealth afforded, come to such a horrific end?
To the investigators who’ve been on the case for the past 10 months—the police and a team of private detectives hired by the couple’s four adult children—the crime presents a series of contradictions. Police found no evidence of a break-in, and the manner in which the Shermans were killed was personal, even intimate. The official cause of death for both was “ligature neck compression,” meaning strangulation by a cord or belt—painful, terrifying, and indicating a passionate desire to see them suffer. Then again, the tidiness of the scene suggested the work of professionals. With little concrete information available, friends and colleagues have projected a tangle of theories into the void, speculating variously about the culpability of rival drugmakers, disgruntled ex-employees, and Russian-Israeli gangsters.
From the first reports, I took a close interest in the deaths. I grew up in Toronto, a proud if irreligious member of the city’s Jewish community. The Shermans and their influence were ever-present there; no museum, community center, or campus seemed to lack a space named after them or Apotex. Their son, Jonathon, and I attended the same high school about a year apart, and our parents were well-acquainted. My father, also named Barry, served a term as a Liberal member of Parliament in the 1990s, and Apotex donated to his campaign. Later my parents interacted at times with the Shermans on the charity and social circuits. Initially, I was reluctant to write about their deaths, which seemed simply too close to home. Yet as the weeks wore on without answers, the story became impossible to ignore, and I booked a ticket to Toronto.
I’d assumed that in writing about Barry Sherman’s life, I would be reporting on a world I knew. And while, yes, he was a consummate member of Canada’s political and business elite, comfortably atop a society that deserves most, if not quite all, of its international reputation for orderly predictability, he was also a financial gateway from the staid routine of boardrooms and balls to someplace less savory. The borders between those worlds could be surprisingly fluid for Sherman. Sometimes they didn’t exist at all.
The Making Of A Billionaire
One day when Sherman was about 10, his father, Herbert, took him to his office at a factory in downtown Toronto and put him to work counting zippers, 20 to a box. When he’d finished, Sherman later wrote in a never-published memoir, his father “exhibited surprise at the number of boxes I had filled, apparently more than would have been done in the same time by any of his paid staff.” When Herbert started checking the boxes, Sherman recalled, “I was extremely offended that he doubted that my counts would be accurate.”
It was an early sign of Sherman’s determination and prideful streak, both of which went largely unwitnessed by his father, who died of a heart attack not long afterward. Awkward, unathletic, and prone to arguing with religious friends about the folly of believing in God, Sherman was an exceptional student. He majored in engineering physics at the University of Toronto because, he wrote, “it was reputed to be the most difficult.”
His first brush with the drug industry was working summers as a driver for Louis Winter, an uncle who ran a medical lab and a generic drug distributor called Empire Laboratories. Many of Sherman’s runs were to pick up urine samples for pregnancy tests. He went on to a doctoral program in engineering at MIT; he was in Cambridge when he heard that Winter had died suddenly. Confident he could make a go of his uncle’s company after finishing his Ph.D., Sherman engineered an acquisition. While he was learning the ropes of drug production, he met and married Honey. A daughter of Holocaust survivors, she’d been born in a displaced-persons camp before immigrating to Canada as a child. After about five years running his uncle’s old company, Sherman agreed to sell. The proceeds became seed capital for Apotex.
The generics business is built on a simple premise: When a cheaper, chemically identical substitute for a brand-name drug is available, patients ought to have access to it. The industry’s products took a long time to be broadly accepted, however. Until the 1980s, generics were restricted by thickets of regulation that protected patent holders from competition, leaving only a small part of the market for copies. The landscape in the U.S. changed dramatically in 1984, when Congress passed the Hatch-Waxman Act. The law allowed generic manufacturers to challenge patents in court before they expired and, if successful, to enjoy a lucrative period of exclusive sales.
Eager for a slice of the world’s largest pharmaceutical market, Sherman was one of the most aggressive users of this system, drawing on what colleagues described as a prodigious knack for identifying the vulnerabilities in brand-name drug patents. Apotex was one of the first companies to produce a generic version of AZT, the earliest widely effective treatment for HIV; later it raced to market with a copy of the blockbuster antidepressant Prozac.
By the mid-1990s, Sherman was one of Canada’s most prominent businessmen, appearing for the first time on the Forbes billionaires list in 2000. Although he reliably turned up at charity galas with Honey, who had a wide and affectionate circle of friends, Sherman’s social graces were limited. He was virtually incapable of small talk, and he was an unapologetic workaholic, abstemious to the point of joylessness. At the ski club where the Shermans took their children on winter weekends, he could usually be found in the chalet, bent over a thick pile of documents. His family lived well, and Sherman had a habit of quietly writing checks to Apotex employees who’d run into financial trouble. But he spent next to nothing on himself, driving cars until they fell apart—including a rattling Ford Mustang that one friend worried might be leaking carbon monoxide into the passenger compartment.
The generics business is to a certain extent zero-sum, and in private some rival executives described Sherman in unprintable terms. Attitudes at the branded-pharmaceutical companies, which invented the drugs he sought to copy, ranged from barely tolerant to seething. A Bristol-Myers Squibb Co. executive once recalled him anticipating his turn to speak during a tense interaction like “a divo waiting to sing his aria.” At one point in the 1990s, according to two people with knowledge of the matter, Germany’s Bayer AG, convinced that Sherman was infringing its patents, hired private investigators to recruit Apotex employees as informants and even raised the possibility of planting a stash of (illegal) drugs in his car. (Bayer said in a statement that it “has never called on employees or external service providers to obtain information in a criminal manner” and that any use of “illegal methods” would have occurred without the company’s knowledge or authorization.)
Still, plenty of businessmen play hardball. What made Sherman unique was his habit of entering into side businesses with characters who would never be welcome in the executive suite at Pfizer Inc. An early example was an attempt to invest in a yacht-chartering venture. As Sherman would learn, there were no yachts, only shell companies, leading the creators of the scheme to be convicted of fraud. He later became the largest shareholder of Nutrition for Life International Inc., a multilevel marketer of vitamin supplements whose pitchman, Kevin Trudeau, was a twice-convicted felon fond of lines such as “With my experience in business, I can solve all the problems.” (Trudeau, no relation to Justin, is in a U.S. prison for a conviction stemming from his promotion of the book The Weight Loss Cure “They” Don’t Want You to Know About, whose gnostic secrets included consuming a meager 500 calories a day.)
Toward the end of his life, Sherman was linked to another convicted fraudster, Shaun Rootenberg, who was working to develop an online trivia game. Sherman agreed to invest, then alleged in court that his money had disappeared. According to legal filings, Sherman had been connected to Rootenberg by Myron Gottlieb, the co-founder of Livent, a theater production company that collapsed in one of Canada’s most spectacular accounting frauds; Gottlieb and Rootenberg had met in prison. Then there was Sherman’s long and intimate friendship and business relationship with a notorious Toronto restaurateur, energy-drink promoter, and B-movie auteur named Frank D’Angelo.
Colleagues tried to counsel caution, without success. Sherman seemed to delight in indulging the many suitors who wanted a piece of his fortune. “He always saw the best in people,” said a longtime confidant who asked not to be identified. “Which wasn’t a great thing all the time.”
Sherman’s benevolence to people he felt were on his side was matched by a fierce determination to punish those who crossed him. He was one of the most prolific litigants in Canadian history, engaged sometimes in as many as 50 simultaneous actions—many necessary for generic development, many not.
One particularly famous case dragged on for the better part of a decade and helped inspire John Le Carré’s novel The Constant Gardener. It began in the mid-1990s, when a University of Toronto hematologist named Nancy Olivieri was running clinical trials for an Apotex drug designed to treat thalassemia, an inherited blood disorder. As the trials progressed, she came to believe the drug might be ineffective and unsafe for patients. The company threatened to sue if she disclosed her concerns and, according to a later inquiry by Canada’s national federation of university teachers, criticized the quality of Olivieri’s work to her superiors. Discussions about an Apotex donation to the university that would have been the largest in its history were suspended, the report said, and Olivieri was removed from her position as director of a clinical program for hemoglobin disorders. (The drug was ultimately approved in the U.S. and Canada. Subsequent reviews suggested Olivieri had acted properly; a legal battle between her and Apotex was settled.)
Sometimes, merely winning wasn’t enough for Sherman, even against opponents who lacked his resources. At the time of his death, he was at the tail end of a bitter legal battle with Louis Winter’s children, who claimed Sherman had concealed a 1960s agreement that they said entitled them to 20 percent of Apotex. Sherman won, and on Dec. 6 a judge ordered the Winter siblings to pay him C$300,000 (around $230,000) in legal costs. The day after Sherman and his wife were buried, his lawyers filed his appeal for more money.
The Hard Facts
Honey Sherman arrived at Apotex’s headquarters, a low office block enveloped in blue-green glass and just off a roaring highway on Toronto’s outskirts, late in the afternoon of Dec. 13. It was one of the last days she planned to be in the city before heading to the family’s holiday home in Florida. Barry was scheduled to join her there later in the month. The purpose of her visit to Apotex was much closer to her heart than to her husband’s: a discussion with the builders of their new house in Forest Hill, a central neighborhood that’s home to a substantial portion of Canada’s business elite. Barry had little desire to move, but Honey was determined to design a dream home closer to the social action. The house previously occupying their new triangular lot had already been demolished so construction could begin.
Honey got home before Barry, who often stayed at his office well into the night. Colleagues received a routine email from him that evening about a drug Apotex had in development, according to a person familiar with the message’s contents. No one at the company heard from Sherman overnight, which was somewhat unusual because he often had trouble sleeping. Nor did he appear at his office the next day, Thursday—similarly abnormal, if hardly the stuff of panic. Sherman had no entourage to speak of, declining to employ a bodyguard, driver, or personal assistant beyond a longtime corporate secretary, so his movements were his own. The same was true of Honey, who wasn’t seen that day either.
Toronto police responded to the 911 call at 11:44 a.m. on Friday. Initially they reported only that two people had been found dead. A provincial minister confirmed on Twitter later that day that the deceased were the Shermans. Police told journalists gathered in the snow outside the Old Colony Road house that there were no indications of forced entry and that they weren’t seeking suspects. On Saturday, Canadian media reported that the deaths were being treated as a possible murder-suicide, committed by Barry Sherman.
The couple’s children—Lauren, 43; Jonathon, 35; Alexandra, 32; and Kaelen, 27—were outraged by the suggestion. Late that day they issued a statement saying their parents’ characters were “totally inconsistent with the rumors regrettably circulated in the media” and urging police to conduct a “thorough, intensive and objective criminal investigation.” The notion of Sherman as a murderer did seem deeply strange, not least for reasons of physical capacity. Some friends joked darkly that if it had been a murder-suicide, it would more likely have been the other way around.
To represent their interests, the children hired Brian Greenspan, a respected Toronto criminal defense lawyer whose past clients include Justin Bieber, Naomi Campbell, and a former Mountie jailed for smuggling narwhal tusks across the U.S. border. Greenspan assembled a team of retired police detectives to conduct a separate investigation and began pushing back publicly against the idea that the absence of broken windows or locks meant the Shermans were alone when they died. There were certainly other ways to get in. The house had nine entrances, and friends say the couple would think nothing of opening the front door for a stranger who rang the bell. There was also an outdoor lockbox with a compartment for a key, so the Shermans’ real estate agent could hold viewings when no one was in. The lone surveillance camera at the house was located, oddly enough, in the pool area, but it hadn’t been turned on for a long time, perhaps years.
The family also hired a pathologist to conduct second autopsies of the bodies. Among the findings that struck their investigators as most significant, according to a person familiar with their work, were narrow markings on both victims’ wrists—evidence that, although no bindings were found at the scene, their hands had been tied at some point. Also odd was the position of Barry’s legs, crossed in front of his body in a manner that hardly suggested the thrashing of a suicide.
The private investigators briefed the police on their conclusion that a murder-suicide couldn’t be the correct explanation, the person said. More than a month after the bodies were found, police officially endorsed that view. On Jan. 26 a homicide detective, Susan Gomes, told reporters that the police were now describing the case as “a double-homicide investigation” and that “both Honey and Barry Sherman were in fact targeted.” Asked what had convinced police, Gomes replied “six weeks of evidence and its review” and refused to elaborate.
This short briefing remains the most recent substantive update from Toronto police, a level of reticence unusual even for Canadian cops, who tend to be tight-lipped. A detective leading the inquiry, Brandon Price, didn’t respond to requests for comment; on Oct. 19 a spokeswoman told Bloomberg Businessweek that the force had no new information to provide.
In this vacuum, the theorizing about the Shermans has taken on a Murder on the Orient Express quality, with everyone a potential suspect. During more than 40 years in the generics industry, Sherman had cost his competitors billions of dollars. His fierce conflict with his cousins, the Winters, was also well-known. But more suggestive, to many, was Sherman’s affinity, if not affection, for inadvisable financial relationships.
Mr. Tough Guy
“They’re f---ing criminals, that’s what they are,” Frank D’Angelo said into his phone. He quickly hung up. “F---ing banks. Gangsters. And they say Italians are gangsters.”
We were sitting at a corner table, backs to the wall, in an Italian restaurant at Toronto’s Ritz-Carlton hotel. D’Angelo had asked me to meet him for an early lunch to discuss his relationship with Sherman, his main financial backer for about 15 years. The two talked almost every day, and D’Angelo was among the last people outside Apotex to speak with Sherman, in a late-evening phone call the Tuesday before the bodies were discovered. It was a regular catch-up, D’Angelo recalled, entirely unremarkable in its content.
“He was my best friend. He was my brother,” he said, visibly choked up at the thought of Sherman’s death. “And I f---ed him, because I couldn’t help him. I couldn’t be there, Mr. Tough Guy, when he needed me the most. It destroys me. I can’t even imagine what he felt.”
A waiter soon arrived to pour him a glass of Brunello, suggesting that the wine might need to breathe for a few minutes. “Breathe, my ass,” D’Angelo said, raising the glass to his mouth. “My mother had Brunello and Amarone on each tit.” It was a little after 11:30.
D’Angelo was wearing a green shirt with a chain-link pattern and a silky finish, untucked over trim jeans. In his left ear, beneath a mop of thinning black hair, was a single diamond earring, and he had chunky rings on both hands. He handled the ordering, and servers soon arrived with a heaping caprese salad and an antipasti plate piled high with pork and duck prosciutti, salami, and manchego and truffle cheeses. More wine followed.
The two men had met in the early 2000s. D’Angelo was in the juice trade, and he’d heard that Sherman owned a state-of-the-art fruit-concentrate plant he was planning to close down. (Sherman had invested in the plant at the urging of an Orthodox Jewish financier, Stephen Mernick, who’d once attempted to engineer a $65 million deal to buy PTL Club, the televangelist TV network founded by Jim and Tammy Faye Bakker.) D’Angelo went to see Sherman at Apotex, and the billionaire took a liking to his latest suitor. Instead of simply selling him the juice plant, Sherman proposed a partnership, which soon grew to include a small brewery he owned next door. Initially, D’Angelo tried to find buyers for its equipment at a decent price, and when he couldn’t, the pair decided to become beer barons instead.
Sherman soon became D’Angelo’s primary financier and adviser, underwriting frenetic marketing campaigns for their new beer brand, Steelback, and other products including an energy drink called Cheetah Power Surge. D’Angelo’s flair for self-promotion saw him become something of a minor Canadian celebrity. He starred in his own ads—including one memorable performance in which he prompted Ben Johnson, the sprinter who’d been stripped of an Olympic gold medal for using steroids, to proclaim, “I Cheetah all the time!”—and belted out the national anthem for Canadian Football League crowds with his band, Frank D’Angelo and the Steelback 2-4.
For Sherman’s colleagues at Apotex, the friendship could be hard to understand. “Some of that stuff just left you shaking your head,” Bruce Clark, a former regulatory affairs executive, later told me. “You’d come in some days, and D’Angelo would be in his office, and Barry would have a case of Cheetah outside his door. Like, you’ve got a global pharmaceutical company with all these high-tech, brilliant people in the building, and you’ve got this energy drink piled up in the hallway.”
Frank’s endeavors lost a lot of money, and when his company, D’Angelo Brands, filed for bankruptcy in 2007, it owed Sherman more than C$100 million. Sherman took control, installing his son to run the company. But he kept financing D’Angelo’s ventures, including his movies. D’Angelo has directed eight films since 2013, largely paid for by Sherman. One, Sicilian Vampire (2015), features James Caan, Daryl Hannah, and a star turn from D’Angelo as a mobster who’s transformed into a bloodsucker after being bitten by a bat. (“Of all of Frank’s films, Sicilian Vampire … is undoubtedly the Frankiest,” read the Globe and Mail’s one-star review.) As D’Angelo described it, movies looked like a low-risk investment to Sherman: Canada has generous tax credits for film production, and one hit, however unlikely, could wipe out the losses from a dozen flops.
Nor did a high-profile encounter with the law shake Sherman’s loyalty. D’Angelo was acquitted of a sexual assault charge in 2009; weeks later, prosecutors accused him of obstruction of justice, claiming he’d conspired with a police sergeant to tilt the earlier trial. (The charge was ultimately dropped; the sergeant, Michael Rutigliano, was accused of more than a dozen corruption-related offenses in one of Canada’s most sensational law enforcement scandals, though all were eventually withdrawn.)
D’Angelo said he was as confounded by the Shermans’ deaths as anyone else—and that he had nothing to do with them. “Frank D’Angelo?” he said, mimicking an investigator crossing off suspects. “The worst thing that could have happened to Frank D’Angelo is Barry dying.” Sherman, he said, was “my f---ing leprechaun, my four-leaf clover.” Price, the lead detective, interviewed D’Angelo earlier this year, and D’Angelo said the questions were “typical shit. I’m pretty sure he was trying to get a psychological profile about me and see if I had any reason to lie.” The detective, D’Angelo continued, “would ask the same question three or four times, moving around,” feigning surprise when his subject pointed out the repetitions. They included “the million-dollar question: ‘Who do you think did it?’ Well how the f--- do I know? You’re the cop.”
But like everyone in the Shermans’ orbit, he had his theories, which he expressed Godfather-style. “I think somebody came to make Barry an offer he couldn’t refuse, and he refused,” D’Angelo said, suggesting that someone wanted Sherman’s cooperation, his money, or both, and that Sherman wouldn’t yield. And “Honey had to die because somebody felt she would get in the way of the scratch.”
We were on to dessert, washed down with more wine—our second bottle. “Money,” he said, spitting on the floor with an audible splat. “F--- it.”
A few minutes later, we walked out of the hotel together. As we prepared to part ways, D’Angelo pulled me close. “Do the right thing for my friend,” he said. “If you don’t, I’m going to come to London and find you.”
A Winter’s Tale
The person with the most obvious reason to confront Sherman at the time of his death was almost certainly his estranged cousin, Kerry Winter. Winter and his siblings—the children of Louis, who’d hired Sherman at Empire Laboratories in the 1960s—spent much of the past decade fighting Sherman in court, claiming he’d concealed a provision in his acquisition of Empire that would have let them buy 20 percent of its shares if certain conditions were met. They further argued that Apotex wouldn’t have existed without Empire to build upon—and that they should therefore receive the same proportion of Apotex, or the cash equivalent. But then the judge threw out their claim, finding that Sherman had acted properly and that any such provision disappeared with his sale of Empire. The timing of the ruling, so close to the murders, looked suspicious to just about everyone involved—something Winter well understood.
I first spoke to Winter in late April, when I called him to ask if we could meet in Toronto. He was initially enthusiastic, but when I later tried to confirm our appointment, he was hesitant. “I’ve been told I’m a prime suspect,” he said, almost apologetically, asking that I give him time to consult with his lawyer before he committed to an interview. Two days later he emailed, suggesting lunch at United Bakers, a vast canteen devoted to Ashkenazi comfort food in a heavily Jewish neighborhood. He gave me the address, unnecessarily—I’d been there dozens of times as a child for potato latkes and split-pea soup.
Winter arrived alone, looking slim and much younger than his 56 years, wearing a navy blue polo shirt and jeans under a slightly frayed Nike windbreaker. He ordered a niçoise salad; I stuck to the hits, with a platter of lox and a bagel. After Sherman’s sale of Empire, Winter told me, the four siblings lost touch with their cousin for years. When they reconnected in 1988, Kerry was addicted to crack cocaine; his brother Dana was also struggling with drug addiction. Sherman reacted with generosity, writing checks and bankrolling his troubled kin’s business ideas. Kerry got clean, got married, and went to work building homes, developing a close relationship with Sherman along the way. (Dana was less fortunate, dying of a heroin overdose in 1995.) The amounts involved were substantial: According to court filings, Kerry alone received about C$8 million in help over the years.
Sherman became a sort of substitute father, Winter said, filling the void left by Louis’s death. Eventually, though, he and his siblings grew suspicious of Sherman’s motives. They began seeking documentation from the sale of Empire and became convinced that he owed them far more. “Barry Sherman was bribing me,” Winter recalled. “I grew to hate him.” The Winters first sued Sherman in 2007. Sherman fought back hard, cutting off his cousins financially and countersuing to recover the funds he’d provided. “When I sued him,” Winter said, “I broke his f---ing heart.” (He and his siblings continue to press their claims against the Sherman estate, though their legal options are narrowing. An appeal was thrown out in August.)
“I had plenty of opportunity—and motive—to kill Barry,” Winter acknowledged. He’d been working as a supervisor on building sites, where “nobody’s watching me. I don’t punch in, I don’t punch out. I start my day when I want, I leave when I want. I take lunch when I want. … But I didn’t do it. It’s the truth.” On the night of Dec. 13, he said, “I watched Peaky Blinders. I like Netflix. I went to a Cocaine Anonymous meeting, every Wednesday I go.” The fact that Winter was still free suggested the police, who’d interviewed him at length earlier this year, accepted this alibi.
He was convinced the true culprit was obvious: Sherman himself. His first reaction when he heard the news, he said, was, “I can’t believe it. He finally snapped.” In Winter’s telling, the Shermans’ marriage was rocky, and his cousin’s outward kindnesses masked a capacity for wrath. “When he lost his temper, the ceiling would shake,” Winter said.
He repeated to me a claim he’d made to Canadian media—that in the 1990s, Sherman, supposedly miserable with his home life, had asked him to help kill Honey. “Could you find somebody to get rid of her?” Winter said Sherman had asked. His reaction, he said, was incredulous: “F---! Barry’s asking me to arrange a f---ing whack job on his wife!” Yet Winter claimed he’d gone as far as asking an underworld-connected friend to help set up a hit before Sherman changed his mind. (In a statement, the Shermans’ children said they were “deeply hurt, shocked, and angered” by Winter’s claims, which they called “outrageous and baseless.”)
The police, Winter argued, had been pressured by the Shermans’ heirs and their allies into abandoning their initial murder-suicide theory, embarking on a sham investigation to preserve the memory of a well-connected philanthropist owed favors even in death. He spoke at times with the quiet intensity of a conspiracy theorist, telling me he was worried that “they” were going to stop him from talking to me, perhaps by putting “bracelets on me and charging me for a double murder.” When emphasizing what he viewed as a lightning-bolt moment of insight, he had an arresting habit of snapping his fingers, pointing ahead, and raising his voice into falsetto.
But despite Winter’s grassy-knoll tendencies, he did have a point. It was difficult to understand how evidence that appeared obvious to a team of retired detectives hadn’t immediately been viewed the same way by active ones. And the Sherman family undoubtedly enjoyed greater-than-average access to top officials. Shortly after the couple’s death, the mayor, Tory, had been criticized for relaying the children’s complaints about leaks of the murder-suicide possibility to police brass, whose subordinates duly clammed up.
Still, it was hard to credit Winter’s essential argument: that to spare a dead billionaire’s reputation, a busy big-city police department was essentially simulating a major murder inquiry. Mistakes, not malice, were a much more plausible explanation for the police’s reversal.
Company Men
Sherman spent most of his waking hours at Apotex headquarters. His parking space was immediately next to the entrance, a double door framed by an oversize letter “A,” rendered in gunmetal gray steel. When I visited in June, the spot was still empty, blocked off with a metal crowd-control barrier and decorated with fresh bouquets of bright flowers. Across from the receptionist’s desk inside, at the base of a narrow atrium, there was a tall, vertical banner printed with a picture of Sherman, wearing a monogrammed lab coat and a proud grin.
I was there to see Jack Kay, Sherman’s right-hand man of more than 30 years, who’d been named chief executive officer in January. He was working out of Sherman’s old office, just a few steps from reception. The Apotex founder rarely discarded a document, and it had taken a team of lawyers to sift through the towering piles of legal pleadings, patent filings, and scrawled notes that once covered every surface. Now it was clean and corporate, with a few neat rows of files and a shelf of souvenir pill bottles.
Eager to report this story the way I would any other, I was careful not to mention my background when I requested an interview with Kay. He knew it anyway. “You’re Barry’s son,” he said as I entered. “I know your father.”
At 77 years old, Kay is slight, with a thin fuzz of white hair—Sherman’s physical and temperamental opposite. As Apotex grew, he enjoyed its material fruits more enthusiastically than his self-denying partner: His car, parked in the spot next to Sherman’s, was a late-model Mercedes roadster with the license plate APO KAY. His old workspace had also been next to Sherman’s, separated by an anteroom containing a lab bench that Sherman used to experiment with formulations. The men sometimes communicated by yelling across the space, and after hours they would sit together for friendly debates, often about religion. Kay shared Sherman’s atheism but didn’t think his friend needed to be so strident about it.
Kay had been in New York to see Andrea Bocelli perform at the time the Shermans were killed. He was still stunned, reduced to open-ended speculation about what had happened. “I knew 99 percent of what Barry was engaged in, and none of it makes any sense,” he said. “What did they do, either Barry or Honey or together, that enraged someone to do what they did?” He wondered if there may have been “some commitment that he made that he didn’t live up to, because the person that he made the commitment to didn’t deliver on his side.” Perhaps, he continued, that person “might have made promises to someone else, and reacted in rage.”
I asked Kay if he thought he’d ever know the truth. “No,” he replied. “There’s only one possibility: that someone will be convicted of a crime in Toronto, and when it comes time for sentencing will say, ‘I have information.’ That’s the only hope. And I’ll probably be long dead when that happens.” Sometimes, Kay said, “I sit up and look at his picture, and my mind just goes blank.”
It hadn’t been easy for Kay to restore normalcy at Apotex, and not only because of Sherman’s death. Much of the generics industry is in crisis, squeezed on one side by buyers’ demands for lower prices and on the other by hungry rivals, mostly from India, which are rapidly building market share. Sherman never took outside capital, and he owned more than 90 percent of Apotex’s shares—a holding that’s passed to his children, none of whom works in the business. Proud of his roots, he maintained far more of the company’s production in high-cost, high-wage Canada than less sentimental owners would have countenanced. More than half of what Apotex makes comes from in and around Toronto, one of North America’s most expensive cities. Some is produced in a warren of factory spaces surrounding Apotex headquarters; more comes from an iceberg of beige concrete several miles west, which occupies most of a city block and churns out 9 billion pills a year.
For the moment, Kay told me, he was trying to fulfill Sherman’s legacy by “keeping the company moving forward until the beneficiaries decide what they want to do.” Many in the drug industry expect that decision will be to sell Apotex, whether to a competitor or a cost-cutting private equity buyer. The company is already shrinking its footprint, shedding assets and cutting off product lines. In mid-July it sold its European generics business to India’s Aurobindo Pharma Ltd., and it has hired consultants from McKinsey & Co. to standardize its financial records and streamline operations.
Even while Sherman was alive, Kay said, “the plan was, eventually we’d have to sell the business, and we’d sell to someone that would keep the jobs in Canada … and we’d take less money for the right guarantees”—at least for a few years. “You can’t rule from the grave.”
Old Haunts
The Shermans retain a ghostly ubiquity in Toronto. One day while I was in town, I went to the Art Gallery of Ontario, the city’s largest art museum, to check out a much-heralded show of works by the abstract painters Joan Mitchell and Jean-Paul Riopelle. On a wall above the canvasses in the first room of the exhibition, I saw the silvery lettering: “Honey & Barry Sherman Gallery.” Later, at an event for the United Way, I spotted their names heading a roster of big-ticket donors.
Near the city’s northern boundary, a crane towered over the Sherman Campus, a vast Jewish community center undergoing extensive renovation. The couple was laid to rest nearby, in a cemetery slotted between concrete apartment complexes and a high-voltage transmission corridor. The day I visited was bright and blustery, with a hint of winter still in the air. There was no obvious directory, and I asked a groundskeeper for help. He knew immediately where to go. The graves were in a distant section of the cemetery, so he gave me a lift on his green riding mower, past tombstones marked with names such as Schoenbach, Levy, Ritter, and Kahn. Jewish families often wait as long as a year to place stones, and the Shermans’ plots were marked only by twin plastic plates supplied by the funeral home: Barry on the left, Honey on the right. On the grass between, someone had left a few stems of white orchids.
It looks increasingly unlikely that anyone will be arrested for their murders. There’s little sign of momentum in either the police or private investigations; a person close to the family said recent police updates have tended to cover leads that haven’t panned out.
Sherman loomed uncommonly large in the lives of people around him: for D’Angelo, as a generous benefactor, loyal to a fault; for Winter, as an object of consuming rage; for Kay, as a partner and intimate friend. All of them, and the broader community of which Barry and Honey were so much a part, will probably have to come to terms with never knowing what happened at 50 Old Colony Rd. last December—with an ending known only to its authors. The Shermans had every reason to expect that they controlled their future, until the moment they didn’t, when the boundaries that surrounded two distinguished lives became suddenly, terrifyingly permeable.
—With Yaacov Benmeleh, Cynthia Koons, and Natalie Wong. Title Photo: Peter J. Thompson/The National Post.
(Corrects the credits for the photographer in the cover image and the photo of the police at the Shermans’ home.)