When a real estate agent discovered Barry and Honey Sherman’s bodies, it wasn’t immediately apparent that the billionaire couple had been murdered.
It looked like they were doing “some weird yoga thing,” Elise Stern, the couple’s agent later told investigators. At the time, Stern was giving a tour of the Shermans’ house to prospective buyers and was about to lead them into the basement pool room when she spotted the bodies and then hastily turned them away.
Anyone, no doubt, would have struggled to quickly comprehend the gruesome sight. With their bodies slumped in a semi-seated position, legs stretched in front and their heads held up by belts strapped around their necks and onto a railing a few feet off the ground — this was no typical murder scene.
This also wasn’t the typical way life ended for a pharmaceutical titan like Barry Sherman — even one whose cut-throat style of doing business had won him scorn in the industry.
An academic prodigy, Barry began pursuing an engineering degree at the University of Toronto when he was just 16. After graduating, he enrolled at MIT where he earned a Ph.D. in astrophysics and had plans to work at NASA.
But when his uncle Lou Winter died unexpectedly, Barry’s life took a sudden turn. After teaming up with a friend, Barry decided to purchase Winter’s generic drug company, Empire Laboratories, for $250,000. A handful of years later, the pair sold it to ICN Pharmaceuticals for about $2 million. Seeing potential in the country’s growing generic drug scene, Barry then launched Apotex in 1974. Over the next several decades, Apotex would blossom into Canada’s largest generic drug company and help grow Barry’s personal pot of wealth, which at the time of his death was worth an estimated $5 billion to $10 billion.
Honey, the daughter of two Polish Holocaust survivors, married Barry in 1971. While Barry excelled in the pharma business, Honey devoted her time to philanthropy and was considered the “queen” of the Toronto Jewish Community, with a warm and gregarious personality that was as legendary as her generosity to local causes.
Now, here they were. And the macabre way they were posed in death would turn out to be just one of many mysteries that have surrounded the case ever since.
The murder scene
Barry and Honey Sherman were killed in their Toronto home Dec. 13, 2017. There was no sign of forced entry, little DNA evidence, and the couple were found about 36 hours after their deaths. Barry was 75 and Honey was 70, and although Honey had a slight injury on her face, a forensic pathologist concluded that both died of “ligature neck compression.”
After nearly five years, the murders remain unsolved.
Despite the high-profile nature of the case — the Shermans had risen to such a level of prestige in Canada that Prime Minister Justin Trudeau attended their funeral — the investigation was “badly bungled” by the Toronto Police Department “from the get-go,” the editorial board of the Toronto Star reflected earlier this year.
To be fair, the Sherman murders were anything but straightforward. Although it appears the Shermans were the victims of a targeted hit, the exact way they were killed — strangled instead of shot — felt personal. The Shermans’ wealth would suggest someone was in it for the money. But the people who stood to gain financially the most from their deaths — their four children — didn’t appear to be involved. Barry had a number of offbeat business dealings outside of pharma, but no concrete leads have emerged that suggest a deal went awry.
Where the investigation stands
Still, the police department’s work on the case has sputtered and at times appeared to be at a complete standstill. So much so that the Shermans’ children, who hired their own investigative team immediately after the murders, offered up to $10 million to the public in 2018 for any tips that could reveal what happened that night in their parents’ home.
“My argument has been that there has not been enough progression to justify that this is even still an active case,” Kevin Donovan, chief investigative reporter at the Toronto Star, said in an interview with PharmaVoice.
“I don’t understand how a city as big as Toronto can have a homicide department that so completely dropped the ball."
Kevin Donovan
Chief investigative reporter, Toronto Star
Donovan didn’t know much about the Shermans before they were killed, but he has since become the preeminent journalist on the homicides, reporting on the emerging details of the investigation for the Toronto Star and taking the police department to court several times to request access to documents related to the case. Years of this reporting culminated in his book, “The Billionaire Murders: The Mysterious Deaths of Barry and Honey Sherman,” which was published in 2019.
Although updates now come at an achingly slow trickle, Donovan and the Toronto police are still following new leads.
Last December, the police released grainy video footage recorded on a home security camera of a man walking near the Sherman’s house around the time of their deaths. And in late October, Toronto homicide detectives announced that they’ve expanded their quest for answers to at least five other countries, which Donovan said is probably to follow “a trail of money overseas.”
Meanwhile, the cast of potentially suspicious characters embedded in the Shermans’ story — from the two “odd” men who toured their home just days before the murders to Barry’s embittered cousin who had sued him for $1 billion to an ex-employee accused of espionage — is as thick as a classic whodunit.
And in this case riddled with loose ends, five particularly troubling mysteries still stand out.
Why did it take so long for the police to rule it a double homicide?
Following the discovery of the Shermans’ bodies, the Toronto police department first said that the circumstances of their death appeared “suspicious.” Yet, within a day, the police pulled an about-face and stated they believed Barry may have murdered his wife and then committed suicide. This theory immediately perplexed those who knew the Shermans best.
Aside from the fact that no one in the family believed Barry would take Honey’s life and then his own, the murder-suicide angle had other holes: Because Honey appeared to have been murdered in another part of the house, it didn’t seem possible that Barry, who was not particularly fit, could have moved her body down to the pool room, hung her by that railing and then himself. Marks on both of their wrists also indicated that their hands were zip-tied at some point. Plus, many noted that if a billionaire drugmaker was going to commit suicide, wouldn’t he use pills?
“If this is a murder-suicide by hanging, it will be the first one recorded in history,” Dr. Mary Case, the chief medical examiner for St Louis County, said of the incident.
Despite there being little to suggest a murder-suicide, it took six weeks before the police reset once again and ruled the crime a double homicide. The implications for the delay were massive.
“Video from a homeowner across the road was ignored, DNA and fingerprints were not collected in a timely fashion, the wrong leads were followed,” Donovan wrote in a Toronto Star report last June.
Why did the police drag their heels?
“Throughout the Star investigation, police have refused to say why it took them so long to determine it was a double murder,” Donovan wrote in June.
Whether it was classic tunnel vision, evidence indicating a murder-suicide that the police obtained but never made public, or a lack of experience investigating homicides (The Economist ranked Toronto as the fifth safest city in the world for personal security in 2017), Donovan said the missteps by police continue to gnaw at him.
“I don’t understand how a city as big as Toronto can have a homicide department that so completely dropped the ball,” he said.
Why were they in that eerie pose?
When the Shermans’ real estate agent found their bodies, she wasn’t just struck by the fact that they were dead. She also noticed that they were posed in a way that was strangely similar to two life-sized sculptures of human figures in the couple’s home.
Why would someone take the time to carefully position the bodies like a piece of art the couple owned?
As part of his investigation for the Toronto Star, Donovan discovered that the figures were created in the 70s by a “junk sculptor” named Leo Sewell who crafted his works from repurposed items.
The two sculptures made their way into the Sherman home through friends of the couple who stored them there. Although one of the Sherman children called them “creepy,” Honey must not have agreed. When the Shermans moved to a new home, she asked if she could keep the sculptures, and they became a permanent part of the family’s décor.
Donovan’s investigation into the origins of the sculptures did not reveal any answers as to why the scene was staged the way it was. But, Donovan noted, “I can’t see how it doesn’t mean something.”
Was the pharma industry somehow involved?
The most common conspiracy theories floated around the case involve some kind of plot by Big Pharma. From rumors that an Israeli generics firm was involved to theories that The Clinton Foundation ordered the hit over a dispute related to drugs Apotex sent to Puerto Rico, Haiti and Rwanda for relief efforts — Donovan said he continues to get calls about a potential pharma connection.
It’s not a stretch to say that Barry’s approach to doing business won him scores of enemies in the industry. Apotex had waged hundreds of legal battles, including suits against pharma giants like Pfizer and Merck & Co., under Sherman’s guidance. His appetite for suing competitors was so ferocious, in fact, that one lawyer quoted in Donovan’s book called him “the most active litigant in any industry in Canada.”
Adding fuel to this rumor fire were comments from Jeffrey Robinson, who wrote about Apotex’s long-running battles with Big Pharma in his book, “Prescription Games: Money, Ego and Power Inside the Global Pharmaceutical Industry.” In an interview with the Canadian Broadcasting Corp. (CBC) News, Robinson said Barry told him that he was surprised one of his competitors hadn’t “knocked him off already.”
Of course, legal scuffles in the generics industry — where drugmakers often challenge patents held by other companies — are not uncommon. And as Donovan noted in his book, pharma companies “sue; they do not kill.”
Still, Barry’s litigious nature, which extended far beyond his pharma dealings, could hold clues as to who would have had a motive for revenge.
Throughout the course of his career, Sherman was entangled in a number of shady behaviors Donovan describes in his book, including a tax scheme “involving high-end yachts,” the creation of overseas tax havens to “shield Apotex profits,” and a list of side businesses so long that even those who knew him well couldn’t keep up. In fact, on the day Barry was killed, his “lawyers filed documents in court requesting an early trial date in a case that involved, of all things, a trivia app for smartphones,” Donovan wrote in his book, noting that some of Sherman’s friends had never even heard of the trivia app.
Apotex was also swept up in the wave of price fixing allegations that has roiled the generics industry in the last few years. According to the Toronto Star, the company paid out $100 million to the U.S. government and the state of Texas, and agreed to cooperate in the U.S. Justice Department’s ongoing investigation of widespread antitrust behavior.
And internally, Apotex was also engaged in several legal challenges against former employees in 2017 — including one the company sued for allegedly stealing drug formulations to launch a rival firm in Pakistan, and another with an executive accused of espionage.
One of his most legendary legal battles involved the four children of Lou Winter, the uncle who previously owned Barry’s first pharma company. For over a decade, Barry’s cousins argued in an ongoing suit that because the sale of their father’s pharma business was the catalyst for Barry’s skyrocketing wealth, they were owed $1 billion — about one-fifth of the Apotex fortune. A judge eventually sided with Barry. Yet, in a move that showcased how vindictive Barry could be in court, he asked for $1 million to be paid to him for the legal trouble. About a week before the murders, a judge reduced the amount to $300,000 — a decision the cousins were appealing.
Of all the cousins, none was more publicly enraged by the ordeal than Kerry Winter. A staunch supporter of the murder-suicide theory, Winter claimed that Barry told him two times in the 90s and that he wanted Winter to help him “whack” his wife Honey. In an interview with “The Fifth Estate,” a CBC news show, Winter also admitted that because of his legal problems with Barry, he had fantasized about decapitating him and rolling his head down the parking lot at Apotex. Shortly after those comments, Winter contested that despite his acrimony towards Barry, he had nothing to do with the murders.
Who is the “walking man?”
Last December, police released video footage of what could be the killer on his way to the scene of the crime. In the video, there’s snow on the ground and all else appears quiet on the residential street not far from the Sherman home where the man was captured with security camera footage walking down the sidewalk. Sometime later, police say the camera spotted the man again, walking back the way he came.
After four years of analyzing home security footage from the area, Toronto police said this is the only individual they could not account for — and have appealed to the public for help identifying this “walking man” who police said has an “unusual gait.”
The way that the mysterious man appears in the Sherman neighborhood, leaves, and then seems to fall off the radar has helped feed a common theory that he could have been a contract killer from overseas who fled Canada right after the murders.
Who’s responsible for their deaths?
This, of course, is the biggest mystery of all. At the end of his book, Donovan posits that the killer must have had an “intimate knowledge” of the Shermans “including their routines,” given the timing and location of the murders.
“Did Barry and Honey Sherman know their killers? I believe so,” Donovan writes.
Ongoing intrigue around the Shermans’ estate also suggests that someone close to the family could have played a role. According to Donovan, just weeks before their deaths, Honey told a “very credible” source that she was updating her will — yet no will for Honey was ever found. Information released in Barry’s will showed that the Shermans’ four children would receive the estate upon their deaths. And although police have indicated that other information tied to the estate is a part of their investigation, they haven’t said what exactly they’re looking for.
Given the pace of the investigation and the lingering questions, Donovan said he isn’t particularly optimistic that “an arrest in the case will ever be made.”
Yet, like the police, Donovan is continuing to follow new leads, including the expanding international investigation, which he called “very important.”
“I had two assignments when I started this investigation,” Donovan said. “Find out if it was a murder-suicide, and then find out who did it. The second one is proving harder. But I’m not going anywhere.”
Editor’s note: In late September, the Sherman family sold Apotex to private equity firm SK Capital for an undisclosed amount.
