Who Killed Barry & Honey Sherman? 7 Facts From The New Docuseries That Surprised Me

'Billionaire Murders' tries to untangle the mystery surrounding the deaths of Toronto's wealthy couple.

Associate Director, Editorial
Snapshot from 'Billionaire Murders', a docu-series investigating Barry and Honey Sherman's murders.

Snapshot from 'Billionaire Murders', a docu-series investigating Barry and Honey Sherman's murders.

Bell Media, Lede, Crave

This Opinion article is part of a Narcity Media series. The views expressed are the author's own and do not necessarily reflect the views of Narcity Media.

It's my third year after moving to Toronto from India and the city never fails to hide a surprise or two around its corners (not all of them are unpleasant, of course). But when I recently chanced upon Billionaire Murders, a new docuseries on Crave casting light on the unsolved murders of local pharmaceutical baron Barry Sherman and his wife Honey Sherman, my mind was blown, and disturbed.

The series, based on a book and a podcast of the same name, investigates the events surrounding December 2017, when the bodies of Barry and Honey Sherman were found in their $7 million mansion in Toronto's North York neighbourhood.

Crave | Billionaire Murders | Official Traileryoutu.be

I quickly realized that this was obviously a story of massive interest to the GTA and that the plot-twists have continued to unfurl even till a few weeks back. It's regarded as one of the most high-profile unsolved murder mysteries of the modern era.

But for immigrants and new Torontonians like yours truly, this four-part docu-show offered a peep inside the scrappy Toronto Police investigation, some questionable decision-making on part of the Sherman family, and the alleged involvement of one of their four children.

Of course it piqued my curiosity and I had to dig through all the info available on the case. Here, I've listed the top, most perfectly serpentine ebbs and flows from the docuseries.

For those of you who want to find out more about the case by watching Billionaire Murders, this is a major spoiler alert! Scroll further at your own peril.

Law enforcement (or the lack of it)

Pardon my language, but WTF Toronto police! For starters, they briefed the media on the night of the discovery that there was no indication of forced entry into the Sherman home — and that the search for any suspects was not part of their investigation. The Toronto Star had reported that they were "probing the possibility of a murder–suicide". This mostly ruled out the possibility of collecting forensics and circulating camera footage from around the crime scene to airports etc.

Toronto police headquarters.Toronto police headquarters.Bell Media, Lede

Honey had suffered facial injuries not Barry, which fueled initial police speculation the former was a victim, not the latter. This theory, which eventually the Toronto police themselves tracked back on, received backlash from the Sherman family and was certainly not the first or last blunder during the police investigation. More on that further.

A parallel investigation

The docu-series goes on to detail the response of the four Sherman children to Toronto police's murder-suicide theory, which was not limited to a public statement. They also hired Toronto lawyer Brian Greenspan to set up a private investigation to look into the deaths.

The first episode of the series shows how a parallel investigation ran along with the police's to discover evidence or potential witnesses in and around the crime scene for the first few weeks. Tom Klett, a retired Toronto Police detective with experience in the homicide, drug, and intelligence bureaus, had led this investigation.

Retired chief forensic pathologist for Ontario, Dr. David Chiasson was also hired to conduct a second autopsy, which went on to reveal that Barry and Honey Sherman's hands were tied. This would later become a key piece of evidence to bust the murder-suicide theory.

No search for almost two days

Barry Sherman was the owner of a near $4 billion pharmacy empire, via his company Apotex, while Honey Sherman, a popular local philanthropist. They were last seen on December 13, 2017, the night of which they were killed. Throughout December 14, the duo went missing for several public appearances and commitments individually, but not even one person — friends or family — cast a shadow of doubt about their unusual failures to appear.

The bodies were only discovered once the realtor, who was helping them sell the house, and housekeeping staff showed up for their regular duties on December 15. Something doesn't add up here IMO.

Anyway, when the bodies were discovered, Barry was seated, his legs crossed, on the pool deck; Honey was on her side with a bruise on her face, as mentioned earlier. Coats were pulled down over their shoulders restraining their arms; they were facing away from the water and fully clothed, as per Bloomberg.

Kevin Donovan.Kevin Donovan.Bell Media, Lede

Investigative journalism & how!

Toronto Star's investigative reporter and a true star journalist, Kevin Donovan took centre stage soon after he was assigned to report on this case. It was his exclusive story in January 2018 that first disclosed that the family's investigation team was sure the deaths were murders. The couple was strangled by belts after their hands were tied — how could the Toronto police miss that, right? Anyway, Toronto police were soon forced to admit that they had made a mistake and the deaths were finally treated like murder.

Donovan's investigation for The Toronto Star led to him interviewing hundreds of sources related to the case and he even challenged the access to certain case documents in the courts on at least seven occasions - eventually winning the battle to get his hands on the material. This was in addition to other important footage he had acquired from anonymous sources, including the art work in the main image of this article that was the inspiration behind staging the corpses. He had reported that the positions the bodies were found in nearly matched those of two 1970s-era "junk" sculptures of human figures posed sitting on speakers in the basement.

Donovan also found out another big miss from the Toronto police in the form of the 'walking man' soon enough, before they released it to the public four years after the deaths (can you believe that?). Captured on a CCTV camera in the neighborhood of the crime scene, this 'walking man' was among their list of suspects - only for them to sit on the footage for ages.

Donovan published his investigations in his book, Billionaire Murders, in 2020, which even led to a podcast and eventually this docuseries of the same name. Out of the three parallel investigations — the police, the private investigators and Donovan's, his definitely comes across as the least biased.

Frank D'Angelo.Frank D'Angelo.Bell Media, Lede

The Frank D'Angelo connection

This dark web of secrets had some sort of near-comic relief to it via Toronto entrepreneur, actor, musician and the city's 2023 mayoral candidate Frank D'Angelo — a close business partner of Barry Sherman, but someone who was alleged to be a suspect by some sources in the docuseries. D'Angelo, to my surprise, appears on camera for this docu-series and even discloses that the police spoke to him in connection to the case, although only once and never again.

But what really stuck with me was his relationship with Barry, who the series claims funded D'Angelo's beverage businesses as well as the majority of his nine feature-length films which the latter has written, produced, directed, scored and starred in. Some sources in the documentary claim to have overheard "shouting matches" between Sherman and D'Angelo, but the Toronto mayoral candidate continues to regard his late friend as the only other person he looked up to besides his own father.

But the Sherman family, especially the son Jonathon, envied this relationship, according to Billionaire Murders, and even blocked D'Angelo from attending the Barry and Honey Sherman's funeral. For his sheer confidence in the midst of multiple storms, D'Angelo sure remains one of the most interesting characters from the docuseries.

Accusations against Jonathon Sherman

Speaking of Jonathon Sherman, sources indicated to Donovan that some of the other Sherman family members, including Jonathon's sister Alex, believe that he was allegedly involved in the murders. In the fourth and last episode of Billionaire Murders, Donovan is finally shown to be able to interview Jonathon in an eerie garage, following numerous failed previous attempts. He was able to interrogate his whereabouts on the night of the murder though but remains unconvinced by the alibi offered.

Dramatization of the interview between Kevin Donovan and Jonathon Sherman.Dramatization of the interview between Kevin Donovan and Jonathon Sherman.Bell Media, Lede

Publicly, Jonathon maintains his support for the hunt for the killer(s) and even added his own $25 million to the $10 million reward one of his sisters had offered to anyone coming forward to help the investigation. I've seen too much Succession to believe much of this, but sure, whatever.

The case of Honey's 'missing will'

The contents of Barry Sherman's will were the subject of an intense public trial between Donovan and the Sherman council, who believed that the revelation of it will threaten the safety of the heirs. However, Donovan was able to establish the identities of the trustees simultaneously. He claimed that they were already in the public realm, via a property document in their names. That was his argument — and of course Jonathon Sherman was one of the four beneficiaries. Feel free to draw your own conclusions.

But wait, there's another interesting bit from the docuseries: contrary to initial beliefs, an anonymous person — who claims to have spent a lot of time helping Honey Sherman with her 'physical ailments' and who appears blacked out on camera behind a distorted voice — is certain that they have heard the will mentioned by Honey multiple times. This person also claimed that Honey didn't share a great relationship with her children and hinted at her inclination to rather donate to charities, in extension to her well-documented philanthropic efforts.

Finally, Donovan said he has a theory of who did it and maybe even the police share the same theory. But the question still beckons: who killed Barry and Honey Sherman?

Is there a documentary about Barry and Honey Sherman?

Billionaire Murders is a new docuseries on Crave casting light on the unsolved murders of local pharmaceutical baron Barry Sherman and his wife Honey Sherman. The series, based on a book and a podcast of the same name, investigates the events surrounding December 2017, when the bodies of Barry and Honey Sherman were found in their $7 million mansion in Toronto's North York neighbourhood.

A Crave subscription costs $19.99 per month in Canada and here's how it compares to other similar services.

And if these spoilers have tickled your curiosity, check out the four-part series and let us know your thoughts in the comments.

Alshaar Khan
Associate Director, Editorial
Alshaar Khan is the Associate Director of Editorial for Narcity Media Group and is based in Toronto, Ontario.