The unsolved murder of an unusual billionaire

Last December, Canadian pharmaceuticals boss Barry Sherman and his wife, Honey, were strangled in their own home. No-one knows who did it, or why. Matthew Campbell reports.

Barry Sherman, the billionaire founder of the pharmaceutical company, Apotex. Picture: Al Dunlop/ Toronto Star via Getty Images

Last December 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$7m (€4.68m).

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 centre of the city.

The Shermans weren’t supposed to be home that day. It was mid-morning, and a housekeeper was doing her bi-weekly 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, which was 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, a privately-held, generic drug company, which he founded in the mid-1970s.

It’s now the country’s premier pharmaceutical manufacturer, accounting for one-fifth of Canadian prescriptions, and the rare, large domestic drugmaker not to have been swallowed up by a foreign rival.

With a fortune that the Bloomberg Billionaires Index placed at $3.6bn (€3.15bn), Sherman was Canada’s 18th-richest person, and he and Honey were among the country’s most generous philanthropists, supporting cultural and educational institutions, anti-poverty organisations, 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.

The 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 were mixed with 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 an 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 pharmaceutical firms, 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 centre, 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 with the Shermans on the charity and social circuits.

Initially, I was reluctant to write about their deaths, which seemed 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 savoury. The borders between those worlds could be surprisingly fluid for Sherman. Sometimes, they didn’t exist at all.

The making of a billionaire

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 programme 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 PhD, 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.

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 anti-depressant, 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 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 hard facts

Mourners leaving the memorial service for Barry and Honey Sherman last December. Picture: Richard Lautens/Toronto Star via Getty Images

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 December 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 neighbourhood 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 that previously occupied 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, which was 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 11:44am 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 rumours 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 defence lawyer, whose past clients include Justin Bieber, Naomi Campbell, and a former Mountie jailed for smuggling narwhal tusks across the US 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 not for years.

The family also hired a pathologist to conduct second autopsies. Among the findings that their investigators considered most significant 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. More than a month after the bodies were found, police officially endorsed that view.

On January 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.

In this vacuum, the theorising 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 fucking criminals, that’s what they are,” Frank D’Angelo said into his phone. He quickly hung up. “Fucking 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 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 fucked 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.”

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 thinning black hair, was a single diamond earring, and he had chunky rings on both hands.

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, but which 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 $65m 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 became 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.

With his flair for self-promotion, D’Angelo became 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 endeavours lost a lot of money, and when his company, D’Angelo Brands, filed for bankruptcy in 2007, it owed Sherman more than C$100m.

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.)

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 offences 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.”

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.”

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 co-operation, 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.”

A Winter’s tale

An officer removes the police tape from the Sherman home in January, six weeks after the still unresolved deaths of Barry and Honey Sherman. Picture: Carlos Osorio/Toronto Star via Getty Images

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% 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 neighbourhood.

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 cheques 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$8m 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.”

“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 December 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: “Fuck! Barry’s asking me to arrange a fucking whack job on his wife!”

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 favours 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 emphasising 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 criticised 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.

Right-hand man

Sherman spent most of his waking hours at Apotex headquarters.

When I visited in June, I was there to see Jack Kay, Sherman’s right-hand man of more than 30 years, who’d been named chief executive 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.

At 77, Kay is slight, with a thin fuzz of white hair — Sherman’s physical and temperamental opposite.

He was 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% 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.”

For the moment, Kay told me, he was trying to fulfil 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 the 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 standardise 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.”

It looks increasingly unlikely that anyone will be arrested for the Sherman 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.

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.


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