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The killing of a Toronto pharmaceutical tycoon and his wife made headlines around the world. Now, the culprit’s identity seems more elusive than ever – and the police face urgent questions about how they investigated the case

Barry and Honey Sherman.


On a Friday afternoon late in January, Detective Sergeant Susan Gomes faced a crowd of reporters and a line of cameras jammed into the media room at Toronto police headquarters. Six weeks had passed since two of Canada’s wealthiest and most influential people had been found dead in the poolroom of their mansion at 50 Old Colony Road, in what had become one of Canada’s most high-profile criminal investigations. After weeks of police silence, Det. Sgt. Gomes had news.

“We believe now, through the six weeks of work and review, we have sufficient evidence to describe this as a double-homicide investigation,” she said. “And both Honey and Barry Sherman were, in fact, targeted.”

It appeared to be a significant change in direction, and a long time coming.

Within hours of Barry and Honey Sherman’s bodies being found, a detective at the scene had told media there was no sign of forced entry and that “indications are that we have no outstanding suspect to be going after," the euphemistic language used often by police to denote a murder-suicide.

By the next morning, multiple media outlets, including The Globe and Mail, had police sources confirming that was the tenor of the investigation, and reliable sources confirmed for weeks that the media was on the right track. Sworn police documents later obtained by the Toronto Star described the investigation in relation only to Honey’s homicide, and made no mention of Barry being murdered.

To those who knew the Shermans, the suggestion was outrageous. There were no signs of mental-health issues or past violence, no reported history of abuse, no indications of any serious problems in their lives or relationship. Within hours, the Shermans’ four children released a statement slamming the information from police sources as shocking and irresponsible. Businessman and media personality Frank D’Angelo, who was in business with Barry and described him as a best friend and brother, dismissed the idea as “impossible.”

Even people such as Leslie Dan, who’d been an archrival of Mr. Sherman’s in the pharmaceutical business for years – and wasn’t one to mince words about fundamental differences with his long-time rival – didn’t entertain the idea for a moment. “That’s nonsense. Everybody knows that’s nonsense,” he said. “It’s not a murder-suicide. It’s murder.”

Six weeks later, Toronto police finally agreed. But the finding that the Shermans were victims of a targeted double murder raised big, new questions: Who really killed Honey and Barry Sherman? And, how could the police have apparently gotten it so wrong?

In the year since, the Toronto police’s handling of the case has become almost as fundamental a mystery as the identity of the killer or killers, and the questions have only multiplied. Is it possible that investigators with the country’s largest municipal police service could make such a serious mistake? And, if so, what does that mean for the rest of the investigation, and for the potential of charges or conviction in the future?

At the Shermans' mansion at 50 Old Colony Rd., a realtor preparing for an open house discovered their bodies on Dec. 15, 2017.

The deaths of Barry and Honey Sherman made international news, and the basics of their story soon became grimly familiar. Barry Sherman was 75, a self-professed workaholic who built his company, Apotex, into an empire of generic pharmaceuticals, and in doing so, became one of the richest men in the country. Honey Sherman was 70, the daughter of Holocaust survivors, a vivacious socialite who meticulously ran the couple’s social lives. Together, the Shermans were particularly renowned for their philanthropy, their patronage and influence extending deep into the realms of politics, art, health, education and the Jewish community.

Their bodies were found inside their imposing 12,000-square-foot mansion on the morning of Dec. 15, 2017, by a realtor preparing for an open house.

News of the deaths raged through the upper echelons of business and power around the world, from the mayor to the Prime Minister, through the pharmaceutical industry and the 11,000 employees of Apotex, to the legions of lawyers and litigants in Barry’s multitudinous legal disputes, to the reporters who’d covered him for decades and the snowbird set in Florida, including couples who’d been expecting to play canasta and golf with Barry and Honey the following week.

Mr. D’Angelo, seeing an employee blanch visibly at a news alert on her phone, says he initially thought North Korea set off a bomb.

“I’ll never be able to get over it. It’s the worst kick in the stomach I’ve ever had in my life,” he said later. “I can’t even fathom it.”

Dec. 20, 2017: Flowers and cards lie outside the Shermans' home a day before their funeral.Michelle Siu/For The Globe and Mail

Officers from the local 33 Division and the city’s homicide squad secured the house at Old Colony, working with a forensic pathologist who, police Chief Mark Saunders later said, provided “an extra layer ... of expertise” at the scene. The Sherman family retained high-profile defence lawyer Brian Greenspan, who began building a team to launch a separate, parallel investigation into the deaths.

There were dozens of homicides under investigation in Toronto at that point in 2017, including a resource-intensive investigation into alleged serial killer Bruce McArthur, who was then a month away from being arrested on two counts of first-degree murder. (He now stands accused of killing eight men.)

The Sherman case would quickly come to dominate the public mind and became a recurring topic of gossip and speculation around the city and country – the very same questions being asked by those who knew the Shermans and live in or around such extremes of money and power, and those who could barely imagine it.

In some ways, the murder-suicide explanation could have made sense. Double murders are rare, and murder-suicide is a sadly common explanation for the death of a married couple in the unlikeliest of places.

Stories circulated that Honey had insulted Barry at a dinner party, that they argued about the new house they were building, that Honey used to say it would cost Barry $2-billion to get rid of her. But even flippant comments take on an ominous tone in the wake of a tragedy, and what relationship doesn’t have moments that would look suspicious if held in a certain light? In fact, Honey had told a friend not long before their deaths that she and Barry had never been happier.

Counting further against the murder-suicide theory was the scene itself: The Shermans died from what police described as “ligature neck compression,” and had been found hanging from a low railing beside their indoor swimming pool with belts around their necks, their legs outstretched and their winter coats pulled back over their arms. The scene’s arrangement conveyed a baroque drama and would have been physically challenging to compose – which didn’t accord with either Barry’s personality or physical capabilities. Beyond that, it didn’t look like a murder-suicide scene. Nothing about it made sense.

“I’ve been asked a thousand times by everybody: ‘What do you think?’ If I knew, I’d be a homicide detective. I don’t know, and I’m not going to hypothesize,” said Mr. D’Angelo, before adding that he is certain of just one thing. “Barry was murdered for money,” he said. “All I’m telling you is this: For somebody to get murdered in their own home, it’s personal. End of story.”

Dec. 15, 2017: Police can be seen as they work around the scene at 50 Old Colony Rd.Cole Burston//For The Globe and Mail

Police and the private investigators have never spoken publicly about a potential motive in the case, but the theories were plentiful. Depending how you perceived it, the scene looked either professional or amateurish; the murders were either a clean and deliberate hit, or the kind of sloppy violence that can only be personal. Family and business relationships were scrutinized. Online, armchair detectives weighed in with their own conclusions and conjecture.

Stories circulated that Barry and Honey Sherman were killed for a new medical marijuana pill he’d formulated; by Israeli assassins in retaliation for corporate espionage; by a Russian hit squad upset with his movement into the Russian market; by Hells Angels who’d been stealing fentanyl from Apotex. There was even a conspiracy theory involving the Clintons.

Despite his wealth and prominence, Barry appeared unconcerned about his own security – he even included his home address on a corporate news release in 2015 – and the Shermans' $6.9-million home and the luxuries it contained had appeared in an item on Toronto Life magazine’s website days just before their deaths. There had been a series of break-ins in the neighbourhood shortly before the murders and, years earlier, a rash of violent home invasions targeting the rich in Toronto, all of which at least raised the possibility of a robbery gone wrong.

And there was no small number of people left angry or disgruntled after their interactions with Barry, which made for nearly endless possibilities. Jeffrey Robinson, who wrote Prescription Games: Money, Ego, and Power Inside the Global Pharmaceutical Industry, described Barry as a “very, very tough businessman who would go right up to the line and wanted to win at all costs,” working in a high-stakes industry pitting him against others who shared those same qualities. He recalled Barry saying, decades earlier, that he was surprised no one had him killed.

“You say to yourself: ‘Who would hire a professional to kill Barry?’ Well, there’s a long list,” Mr. Robinson said. “Or, there might be a conjectured long list. Whether they would go so far as to murder somebody is another story.”

On that list was almost certainly Barry Sherman’s estranged cousin, Kerry Winter, who’d been engaged in an acrimonious, decade-long lawsuit against Mr. Sherman and who had, just days before the murders, been ordered to pay the billionaire’s legal costs. Mr. Winter soon emerged publicly with an allegation that Barry had tried to hire him in the 1990s to have Honey “whacked.”

In an appearance on The Fifth Estate, Mr. Winter also admitted he’d thought about killing Barry, but said he’d planned to do it by decapitating Barry in the Apotex parking lot, then waiting for police to arrest him. (He’s been similarly blunt about his feelings about the Shermans with The Globe.) On the front page of the National Enquirer, the headline blared “Canadian Billionaires’ Contract Killing: The Cousin DID IT!”

Mr. Winter has since become a fixture in coverage of the case, steadfastly promoting his view that the Shermans’ deaths were indeed a murder-suicide, which he contends is being covered up by police and the family to protect Barry’s legacy. Mr. Winter, who has both described himself as the “prime suspect” and expressed concern he could be framed for the murders, says he spent the night the Shermans are believed to have been killed at a Cocaine Anonymous meeting and then at home, watching Peaky Blinders on Netflix.

“l had opportunity and motive/reasons to kill Barry,” he said recently in an e-mail exchange.“l simply didn’t.”

Mr. Winter says he’s been interviewed by police, but believes he’s no longer a suspect.

“Honestly, it’s such an obvious cover-up,” he said in another exchange by text. “Do you believe the cops [messed] up so bad?”

Oct. 26, 2018: Brian Greenspan, a lawyer for the Shermans' family, sits alongside former police officer Mike Davis at a Toronto news conference.Chris Young/The Canadian Press

With little visible movement in the case, the Sherman family’s lawyer, Mr. Greenspan, organized a news conference at Apotex in October to announce a $10-million reward as a new incentive for anyone with information to come forward. Flanked by retired police officers working on the family’s private investigative team, Mr. Greenspan also offered harsh criticism for the Toronto Police Service, which he said failed to meet the professional standard expected – and required – of police, beginning with the early “misguided, indeed unfounded, conclusion” that there had been no forced entry and that there were no outstanding suspects.

Mr. Greenspan particularly questioned how officers could have failed to recognize “the suspicious and staged manner” in which the Shermans’ bodies were found, and said investigators failed to properly collect evidence at the crime scene, including missing at least 25 palm or fingerprint impressions and not properly examining the locks and possible entrances to the home. If they had, he said, “they would have located the point of entry to the home, which would have seriously undermined their misleading and irresponsible conclusion that there had been no forced entry.”

“It has never been our intention to alienate the Toronto Police Service or to conduct an audit of their performance,” Mr. Greenspan said. Instead, he proposed a private-public partnership, unprecedented in homicide investigations, in which the Sherman family would provide additional resources to “enhance” the police investigation.

“It remains the belief of the Sherman family [that] by working together, we will increase their chance of finding justice,” he said.

Toronto Police Chief Mark Saunders has supported his officers' handling of the Sherman case.

The year since police were called to 50 Old Colony Road has been Toronto’s deadliest on record. There have been 92 homicides so far, including a van attack that left 10 people dead.

Chief Saunders did not agree to an interview, but has stood staunchly by his officers and their investigative and forensic work on the Sherman case. He says the investigation has included 50 officers, more than 200 witnesses, 4,000 pages of documents and 2,000 hours of video, and that those looking at the case from the outside – including the public and the family’s investigators – don’t have all the information or context.

“Homicide investigations are dynamic, they’re fluid in nature, and the best persons to make the decisions in real time are the lead investigators, the highly trained lead investigators,” Chief Saunders said at his own news conference in response to Mr. Greenspan’s statements.

“Members of the Toronto Police Service do the most homicides in Canada. They are challenged and scrutinized more than any others, and rightfully so, and they accept that challenge. But I will tell you they have a very high conviction rate and it’s because of their professionalism. It’s because they understand law, they understand how to gather evidence [and] present it properly.”

Veteran homicide investigator Rod Buckingham, who now heads private security and consulting firm Buckingham Security Services, says homicide investigators are typically highly trained and experienced officers, and he cautions that how things appear from the outside may not reflect what is actually going on with the investigation.

“Sitting back, it’s easy to criticize, but I’d be very hesitant about that,” he said. “There’s all sorts of checks and balances within policing to determine how the investigation was done, and I would just say that homicide detectives have got one mission: To solve that crime. And I fully expect that’s exactly what they are doing.”

Chief Saunders says homicide investigations have no timeline. Yet a year feels long, and the truth of what happened inside 50 Old Colony Road seems more elusive than ever.

On an overcast day in December, the house stands dark and still, its façade more familiar now as a crime scene than a home. On one side of the property, a piece of police tape remained tied around a tree and a pole, its loose ends flapping in the wind.

And in a cemetery not far away, a broad grey headstone marks two lives, with one ending.

“Mom and Dad were beloved leaders and members of our community,” the inscription reads. “And they are dearly missed by all who knew and loved them.”

With reports from Victoria Gibson and Molly Hayes

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