The real estate agent thought it was just another showing. Inside, she found two dead billionaires.

For 30 years, billionaire Barry Sherman and his wife Honey, had lived quietly at a house on Old Colony Road in Toronto.

The pharmaceutical magnate was one of Canada's richest men, a dedicated philanthropist, and a staunch supporter of Prime Minister Justin Trudeau.

But in 2017, 70-year-old Honey decided it was time to move a little closer to the city, so she and Barry, 75, put the home on the market. They listed the home for AUD$5.5 million and built a new AUD$27.5 million mansion in the exclusive enclave of Forest Hill.

But they never made it to their new home.

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In December 2017, real estate agent Elise Stern arrived at the Old Colony Road mansion to show a couple around the home for sale.

The gardener and housekeeper had already been to the home that morning. The alarm had been turned off.

As the agent took the potential buyers to the pool, they spotted the couple slumped over, side by side, on the far deck. Leather belts had been wrapped around their necks and attached to a metal pool railing.

Their arms were tied behind their backs.

The double homicide took the world by storm, as the police, media and the public tried to determine why the billionaires had been slain.

The double homicide shocked the world. Image: Getty.

The murders remain unsolved. But last December, the couple's niece and nephew sued their four children over one of several trusts.

The pair claim the trustees were withholding information, and potentially millions of dollars, thrusting the private family into a public airing of their dirty laundry, that includes private emails, property deeds, wills, and financial records.

Who were the Shermans?

Barry was the owner of the pharmaceutical company, Apotex. It didn't look like much from the outside, as Barry notoriously rejected public depictions of wealth and appearances, himself driving an old Ford Mustang.

Barry had built Apotex into the country's top generic pharmaceutical manufacturer, often by beating rivals to the market, and at one point, exceeding $2 billion in annual sales.

Kevin Donovan, journalist and host of the podcast Suspicion, told Mamamia's True Crime Conversations podcast that Barry was a "chronic workaholic."

Barry Sherman. Image: Getty.

"He was 75 years old at the time of his murder. He grew up in a posh part of Toronto," Donovan said, explaining how the pair met.

"Honey, different upbringing. She was a child of the holocaust. Her parents were in Nazi slave camps during the Second World War. She's born in a displaced persons camp in 1947, and she ends up in Canada with her mum and dad and her young sister.

"They met, as people used to, not through Tinder, but through being introduced to by a good friend of theirs. And they marry in 1973. At the time of their death, they were one of Canada's top five wealthiest couples."

Despite his wealth, Barry dressed casually, never flaunting luxury.

He believed patients shouldn't have to pay high prices for life-saving drugs. But to the pharmaceutical companies that developed the formulas for those drugs, he was little more than a thief.

By all accounts, Barry was obsessed with his work, taking it home and on holidays. Honey often brought her sister Mary Shechtman on family trips, and over time their children grew close.

Over time, their finances also became entangled, with Mary's husband running a mail order drug company and a jewellery firm for Barry at different times.

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The Shermans supported Mary too, paying her to decorate homes, lending her money to buy property and reportedly giving her about $10,000 a month in spending money.

Although the couple didn't waste money, Barry happily provided money and loans to his children.

Honey believed it was too much, and worried her children would become entitled. Mary had the same worries for her own children, and urged them not to ask the Shermans for money.

Donovan said the pair had a "unique relationship with cash."

"It's a very different relationship with money, and that was also an unusual relationship when it came to their children. Barry parented by giving money to the kids, more to some than others," he explained.

Barry and Honey Sherman. Image: Supplied.

A few months before their murder, Mary's son Noah requested access to Honey's credit card, using it to buy designer accessories. Mary threatened to remove him from a family trust that Sherman had set up for them.

"Everyone in the house shares the feeling that you would throw us under the bus for the chance to get to the Shermans and their money," Mary wrote to Noah a year after the murders.

"We each get that feeling individually. Since you don't trust me, there is no reason for me to trust you."

Court records reveal she allegedly had him removed as a beneficiary from her real estate portfolio, and the two haven't spoken since 2019.

An ugly industry.

The moment Stern discovered the Sherman's bodies, speculation started swirling.

Much of the speculation surrounding the murders centred on Apotex and its supply of generic drugs.

In the lead up to the murders, Apotex was facing multiple challenges. The company was suing a former employee for stealing drug formulas. At the same time, the US Department of Justice had added Apotex to a list of drugmakers suspected of price fixing.

Canada's Supreme Court had ruled against them in a long-running dispute with AstraZeneca, leading to a settlement of more than $300 million, and Apotex's chief executive had been accused in a civil lawsuit of receiving industry secrets from a former executive at a rival company with whom he was having an affair.

So it's little surprise, when the Shermans were killed, his business ventures were blamed.

And then there was Mary. She was one of the first people told about the murders. She was distraught.

At the funeral, the Sherman's son Jonathon announced a new foundation in their mother's name.

The funeral of Barry and Honey Sherman, attended by Prime Minister Justin Trudeau. Image: Getty.

"We would like our Aunt Mary… to help guide this foundation in a way that best honours our parents," he said.

But things were becoming tense. The Sherman's children were becoming weary of Mary and her children. Mary reportedly insisted that her sister had promised her hundreds of millions of dollars.

But Honey hadn't left a will, and so the entire estate passed directly to the four Sherman children, who cut Mary off shortly after the funeral. This decision plunged Mary into financial struggle, with her husband forced to drive an Uber to make ends meet.

Unanswered questions.

According to reports, Jonathan no longer speaks to his three sisters, and two of Mary's children have now sued the Sherman children and other administrators of a trust worth more than AUD$440m.

The suit claims that the trust was established to benefit Mary's children and the children of Barry's sister Sandra Florence, as well as the Sherman's children.

The trustees include Jonathon, Brad Krawczyk, the ex-husband of one of the Sherman daughters; and Alex Glasenberg, who runs the Sherman holding company.

Following their parents' murders, the Sherman children hired one of Toronto's most famous criminal defence attorneys, Brian Greenspan, to build a team of retired detectives to conduct their own investigation.

While they handed their findings over to police, the case remains open and ongoing, with only one dedicated detective remaining.

Donovan has extensively investigated the case and said the way the bodies were found suggests the crime scene was staged.

"They're in a seated position. Their buttocks are on the floor, but they're tilting backward, and the force of the belt is around the back of their neck," he said.

"And Barry and Honey, both of their shoes are on. Barry's feet are crossed in a very passive manner. His eyeglasses are perched neatly on his head.

"These are all things that in my investigation, you know, the police should have picked up as signs of a staged crime scene, but they didn't."

Feature Image: Supplied.

This article was originally published in May 2024 and has since been updated.