The Sinister and Mysterious Unsolved Murders of a Billionaire and his Wife

Bernard Charles “Barry” Sherman seemed to have the world at his fingertips. The founder, chairman and CEO of the largest Canadian generic drug maker Apotex Inc., Sherman was the 12th-wealthiest man in Canada, and was happily married to his wife, Honey, the daughter of two Holocaust survivors and a respected figure in the Toronto Jewish community. The couple were not only fixtures of the Canadian high society scene, but they were also extremely generous philanthropists, giving tens of millions of dollars away to various hospitals, schools, and charities, and had buildings named in their honor, and they frequently sent medicines to stricken disaster zones. The two of them had been planning a new chapter in their future together, listing their home in Toronto for 6.9 million Canadian dollars and they were building a new home in the city. Their future seemed bright, but there were dark times ahead, and they were about to become the center of one of Canada’s most notorious unsolved mysteries.

December 13, 2017, started off normally enough. That afternoon the Shermans went over some design plans for their new home at Barry’s office, as well as for their plans for a vacation to Miami, Florida. Honey was supposed to leave a few days later and Barry was expecting to take care of some business and join her the following week. They were described as being in good spirits and acting normally, and later that evening he sent a totally routine email to colleagues about a new drug his company was developing. No one would have had any reason to think that anything at all was amiss, but when Barry did not show up to the office the following day without contacting anyone it was seen as incredibly odd. Even so, it still had not sounded any alarms and it was just assumed that Barry was busy with his new drugs, getting ready for the move, and planning for his expected holiday with his wife.

The following day, a realtor by the name of Elise Stern brought by some prospective customers to the Sherman home, not expecting the couple to be there. At first it was a totally normal real estate showing, with the agent showing the prospective customers the main story before taking them down to the area that held the indoor pool and hot tub, and it was here where they were met with a macabre sight. There, sitting on the on the floor next to the pool were the bodies of Barry and Honey Sherman, their necks tied up with leather belts to a railing situated a few feet off the ground. The position of the bodies was odd, in a semi-seated position, legs stretched in front and their heads held up by the belts, with Stern saying it “looked like they were doing some weird yoga thing,” and both of them had their coats pulled down around their arms as if to keep their arms bound. Stern was lucky enough to turn the customers away before they could see the ghastly scene, after which she immediately notified police.

When police arrived, they found no sign of forced entry, no signs of a struggle, and no noticeable injuries of the two bodies other than a very slight scuff on Honey’s face. A search of the house turned up Honey’s cell phone in one of the bathrooms, although it had not been used, and Barry’s gloves, as well as some paperwork related to an inspection of the house, had been left on the floor just outside the garage door, on the way to the basement pool. An autopsy would find that the two had died of “ligature neck compression,” there were no drugs or alcohol in their systems, and the initial police assumption was that this had been a murder suicide, with Honey perhaps being the victim because of the injuries on her face. An eerie detail of the scene was the weird position of the bodies, which were arranged in a way that was spookily similar to two life-sized sculptures of human figures in the couple’s home, although it could not be ascertained if there was any significance to this. The working theory was that Barry had attacked her, tied her neck up, and then done the same to himself, although he had left no note and family and friends strongly denied that he would ever do such a thing. Nevertheless, at the time police considered it pretty much case closed.

In the meantime, friends and family were working with private investigators and investigative reports from the Toronto Star to dig deeper into a dark case the police seemed to have little interest in pursuing any further, and new evidence that they dug up would point to a targeted murder. Not only were the two victims found with their arms bound by coats, but that their hands also held marks to suggest they had been bound as well, making it unlikely that either one of them would have been able to do that to themselves, but there had also been a basement door left open and an unopened window left that way to air out fumes from a fresh paint job, providing access to someone with nefarious intent. A second autopsy also leaned heavily towards the murder angle, and it was additionally found that Honey had likely been killed in another part of the house and dragged to the pool area. Then there was the fact that a murder suicide by hanging just didn’t seem very practical, with Dr. Mary Case, the chief medical examiner for St Louis County, noting, “If this is a murder-suicide by hanging, it will be the first one recorded in history.” The Toronto Star would release a full investigative report of its own that clashed wildly with the official stance, and there was much criticism levelled at the police for their handling of the case, with Kevin Donovan Chief investigative reporter for the Toronto Star saying:

Video from a homeowner across the road was ignored, DNA and fingerprints were not collected in a timely fashion, the wrong leads were followed. Throughout the Star investigation, police have refused to say why it took them so long to determine it was a double murder, I don’t understand how a city as big as Toronto can have a homicide department that so completely dropped the ball.

The additional pressure seems to have worked, because shortly after this the police changed their tune, announcing that they had come to the conclusion that the Shermans had indeed been murdered in a targeted hit, and that “investigators are methodically reviewing material and pursuing different investigative avenues.” As this was going on there was a lot of speculation as to who could have been behind the shocking crime. The most obvious motive was the victims’ enormous wealth, but the ones who stood to financially gain the most from the deaths- their four children- didn’t appear to be involved. Another possibility was that this had been the doing of an enemy Barry had made, which seems very likely considering the fact that he was considered to be an aggressive, cutthroat, and litigious business man in a business that had gained the scorn of big pharmaceutical companies. Barry had even expressed this fear himself, when he once eerily wrote in Prescription Games, a 2001 book about the industry:

The branded drug companies hate us. They have hired private investigators on us all the time. The thought once came to my mind, why didn’t they just hire someone to knock me off? For a thousand bucks paid to the right person you can probably get someone killed. Perhaps I’m surprised that hasn’t happened.

Barry had also been locked in legal problems with his cousin, Kerry Winter, but Winter had an alibi and was found to be not a person of interest, even though he admitted he had had fantisized about killing Sherman at times. It was found that Barry also owed around $1 billion to other companies leading up to his death, so perhaps this might have made him another enemy. Yet another possible motive was pure hate, as Honey Sherman had been very involved with the Jewish community and was very vocal about being Jewish and her belief in Israel’s rights, which could have inspired someone to lash out as a hate crime. There were plenty of chances to make enemies with Barry’s many alleged shady business dealings as well. He was allegedly involved in a tax scheme involving high-end yachts, the creation of overseas tax havens to shield Apotex profits, and a wide variety of various side businesses, and his company had been embroiled with numerous legal battles including price fixing allegations, former spurned employees, and others. There were any number of people who probably wouldn’t have minded if he was out of the picture, and a long list of potential perpetrators.

Yet there was no evidence for any of these, and despite interviewing numerous people police could get no solid leads until 2021, when police announced that they believed a person caught in some security footage was a person of interest because they had spent “a very suspicious amount of time” in the immediate area of the Sherman home around the time the Sherman’s were murdered. However, the video merely shows someone in dark clothing with a distinctive walk, but the face is not visible, with it not even clear if it is a man or a woman and so making it not very useful in the end. 

Despite years of pursuing potential leads and suspects, police have never arrested anyone in connection to the murders, and indeed there is still debate over whether they were really murders at all. A hefty reward offered by family members that has reached $35 million has also failed to produce any solid leads and the case remains completely cold. Ultimately there are no clear answers. Was this a murder-suicide, foul play, or what? If it was a murder then who was it and why? As of yet, the case remains unsolved, and we may never know for sure.