Who killed Barry and Honey Sherman? A new book offers fascinating insights.

The murders of Honey and Barry Sherman, the billionaire couple found dead in their Toronto home in December 2017, remains one of the country’s most perplexing unsolved crimes. In the newly published Billionaire Murders: The Mysterious Deaths of Barry and Honey Sherman, Kevin Donovan, the chief investigative reporter at the Toronto Star, reveals new details of a case he has been examining for two years. Kevin Donovan speaks with Anne Kingston about the flawed police investigation, the fractious relationships within the Sherman family, how the Shermans’ wealth has been deployed to avoid media scrutiny, and what he believes about who might have done it.

Warning: The following conversation contains graphic details, some involving suicide.

Q: Your book reveals that Toronto police weren’t contacted for almost 90 minutes after the Shermans’ bodies were found next to their indoor swimming pool. Is that kind of delay unusual in your experience?

A: It’s very unusual, and I was fixated on it for some time. As far as I can tell, the bodies are discovered, some phone calls were made and the people who made the phone calls don’t want to describe to me why they did what they did. The police are adamant they got their call at 11:44 a.m. All of my research indicates the bodies were found at 10:10 a.m.

Q: Toronto police never said publicly that they believed the case was a murder-suicide, though they talked about “no forced entry” and no search for suspects. You write that police sources continued to tell reporters privately that murder-suicide was the working theory, which inflamed the Shermans’ family and friends. Yet there were also reports that both Barry and Honey Sherman were found with their coats pulled back behind them, which would immobilize arm movements—and rule out murder-suicide. How could police even consider it a murder-suicide?

A: I can’t speak for Toronto police. But, as I understand it, the coats were pulled down but not enough to immobilize them. There’s also the detail about marks found on their wrists indicative of them being bound together; but those ties are removed and cannot be found. I struggle with this. How could you look at that scene and not think this was a case of double murder? The other thing I spend a lot of time trying to figure out was that [the Shermans] were in a seated position on the floor, their backs to the pool. There’s no way you could strangle yourself sitting upright like that. It’s different than jumping from a stool, like we’ve seen in the movies. There’s no fall here. So, in my opinion, there can be no murder-suicide or double-suicide.

Q: So it’s another glaring question mark?

A: Yes, one of the things I’ve been trying to get through my journey through the court process is to find out from police: “Okay, you’re not going to release documents that detail what your theory is now. But give me and the public the first six weeks when it was considered murder-suicide, and let’s see who you talked to and what made you arrive at that wrong conclusion.” There is jurisprudence out there that says media and the public can have access to other theories once they are debunked. I’ve not won that one but am working on it. The true public interest in this—and why media are interested—is “Did our municipally funded force make some mistakes? If so, it’s something that needs to be looked at? Right now, we have the chief of police saying: “My officers did a great job.”

Q: Another unique aspect of this case was the Sherman family, rejecting the murder-suicide theory, hiring noted criminal defence lawyer Brian Greenspan within 72 hours of the bodies being found. He assembled his own team to investigate and later set up a tip-line offering a potential $10-million reward. How did that factor into the investigation?

A: Brian Greenspan’s marching orders, in his words, were to “put a second lens on this.” Then he quickly thinks ‘We need to do a second set of autopsies,’ which I think was a good idea. What I do think is unusual is this lengthy investigation where Toronto police say they now have 343 tips they have to check out—including at least one tip from a psychic. So the police are slowed down by having to check all this stuff out. The other thing I found very unusual—and have never seen in a criminal case—is that there is an enormous reward and the information is to go to the private team and not the police.

Q: Greenspan has framed this as two parallel investigations. But he is representing the family, which was adamant early on about what could and could not be an outcome. So the idea that there are parallel ‘police-style’ investigations is false. Greenspan’s responsibility is to his clients.

A: That’s a good point. Then there is the issue of what he refers to as evidence—how does he get that to the police? Brian Greenspan obtained information that the crime scene was not, in their opinion, properly vacuumed so they found evidence—jewelry found in the driveway that’s wasn’t Honey’s. Police hired a lawyer to receive information from Greenspan and the Sherman family. It must be a maelstrom for the police to work with.

Q: With the tip-line, people are more likely to go where there’s a reward, rather than to police. How is the information relayed from Greenspan’s team to the police?

A: They get information in—emails or calls—they make a note or print-out and put on USB key and take it to the police. There have been 343 tips so far. It used to be on a weekly basis. But that ended on July 2, 2019. That’s the last Toronto Police has heard from the Greenspan team. I don’t know why.

Q: Do you have a theory why it took police six weeks to say it was a targeted double homicide?

A: I do, and I try not to be too self-serving or too Toronto Star-serving. I was asked to investigate on Jan. 6, and I spent a few weeks trying to find out, not who killed them, but whether it was it murder-suicide or double murder. I started interviewing people, including Dr. David Chiasson, a retired deputy chief coroner who happened to be involved in the case, who gave me permission to identify him. I got access to other forensic information—and get a sense of what the private investigators where doing. On Jan. 19, I published that the Shermans were murdered. Dr. Chiasson who conducted the second autopsy was interviewed on Wednesday and on Friday the police held a press conference. As fantastical as it seems, the Toronto police were invited into that autopsy room in December by the private team. They chose not to go or to see the second autopsy report—until it was on the front page of the Toronto Star.

Q: There appear to be so many miscues on the part of police—they didn’t collect DNA, or follow up on interviews. It seemed that either they didn’t take it seriously as a murder investigation, or there was interference, or they were inept, which is how Brian Greenspan presented it. What do you think?

A: It’s a little bit of everything. The Shermans were killed on Dec. 13 and found on Dec. 15. That week was when the Toronto police were closing in on the Bruce McArthur serial murder investigation. McArthur wasn’t arrested until January but a lot of homicide resources were on that case, and not directed at the Shermans. And tragically there are a lot of homicides in Toronto. The fact Honey had injury to her face and Barry didn’t may have fueled thinking it was murder-suicide. The first police-mandated autopsy was done by someone who was not a veteran—and he wasn’t sure. The thinking in the first weeks was that Honey was the victim, not Barry.

Q: In your book, you write about the damage to Honey’s face which suggested the killings had a personal component—that the killer or killers felt differently towards husband and wife. Why was that worth mentioning?

A: I had no access to the police investigation so I’m looking for the clues. And that says to me that the person may have liked Barry more than Honey. But it could also mean that a person attacked Honey and then strangled Barry.

Q: Your book is also a fascinating portrait of wealth—and family dysfunction. You write that Barry Sherman gave his children millions but kept his wife on a tight financial leash—she had access to cash for trips and shopping, but controlled no money of her own. You also report that just before their deaths, Honey told friends her husband was contemplating giving her a big financial gift; her sister, Mary, was also telling people that Honey was giving her a lot of money. Why was this relevant?

A: Honey was given money for her needs but not her desires. If she wanted to put in a very expensive marble floor in their Florida condo, she could do that. Barry wasn’t interested in spending money—he liked to give it away—and felt his wife should be the same way. In the final year of her life, both Honey and Barry told friends she was going to come into between $100 million and $500 million. Then it became known that some of this might go to her beloved sister, Mary. Honey and Mary were very close; they might be the closest relationship in the Sherman family. Honey was tough on her children—she wanted them to have jobs and pay bills. Barry was closer to them; he’d just give them money. From quite good sources, it was not unusual for the two older children to receive $100s of million and the younger two children to receive in the low millions. It was a very dysfunctional situation with money and the Sherman family.

Q: You also report that Honey appeared to have no will, and that there was a search for it. That would have implications in terms of the order of their deaths. Could you explain?

A: Nobody knows who died first. It’s more likely Honey died first. None of her close friends remember her having a will. They looked for a will. I went to court to try to get their wills, which is an ongoing legal battle. The papers filed for Honey are filed for a person without a will—intestate. I’ve seen two papers for Barry—one says he has a will, another says he doesn’t. I find it very confusing. My understanding of the will that I have not yet seen is that it gives money equally to the four children. It sets up a trust for Honey that will provide for her and she would have control over should Barry predecease her. Barry used a basic pro-forma will, like you can buy at Staples. I would have thought there would be millions for charities—but there’s nothing like that.

Q: Jonathon Sherman emerges as an interesting figure in your book. You quote friends of Honey saying Honey and Jonathon “hated” one another, and also detail Jonathon’s complex relationship with his father. Could you speak to that?

A: There’s one son, and three daughters. The daughters were not interested in business. Jonathon is interested in business, and with his father’s financial help purchased a self-storage firm and property in what he sees as the new cottage country. I have a chain of emails in the book from 2015 between Jonathon and his father; it’s quite acrimonious. At the time cash is tight for Apotex; Barry had bet on drugs that didn’t work out; it had happened before and he was going to ride it out. But he didn’t have hundreds of millions to pass around. According to Jonathon, far too much of his father’s money was going to Frank D’Angelo and not to him.

Frank D’Angelo is a colourful person and close friend of Sherman’s [who Sherman bankrolled in numerous business ventures]. Jonathon boldly asks for $250-million to develop cottages and expand his storage business. Barry Sherman responds to lengthy emails with very short one-liners. In the final one, he says D’Angelo is good at making movies, here’s the trailer to his latest one; it was a put-down by Barry to his son. I understand that after that—I don’t have emails but talked to people who did—Jonathon said to his sisters: “Our father may be showing signs of incompetence; maybe it’s time to do something.”

I asked Brian Greenspan about that. He said Jonathon was only being a good steward of family finances, and maybe that was the case. But there was no attempt I could see to have Barry removed. I then tracked financial payments—I can only look where Barry has put a charge on Jonathon’s properties. After this acrimonious discussion there’s no money for a year, then the tap opens up again and in 2017 there’s quite a big payment to Jonathon’s business. It seems that things were much better between them.

Q: The email from Jonathon to his sister you quote has the subject line “to fellow shareholders.” You also report Jonathon wanted to be involved with Apotex succession planning with his business partner.

A: I have probably talked to a half dozen men who were sons of Barry Sherman’s friends. Barry was generous giving people employment. He was desperate to have someone succeed him in the business. Jonathon wasn’t doing that. He was doing his own thing.

Q: You also quote what you call an “eye-brow raising” comment Jonathon made at the funeral about his parents: that he and his siblings were glad “neither of you had to suffer like we are suffering now.” You saw that as worth noting?

A: I think so. Only Jonathon spoke for the family. You can tell it’s been a tough couple of days. You also can read between the lines about some of the comments he made, including mention of his mother falling when skiing, and see the relationship isn’t so great with his mother.

Q: The book also chronicles fractures after the Shermans’ deaths, including Honey’s sister being exiled from the family. You also write about how Jack Kay, Barry Sherman’s right hand at Apotex for 35 years and a trustee of the estate, was the subject of a rumour floated by Jonathon that he was somehow involved in the murders, and he was later kicked out of Apotex. Some of this is stranger than fiction.

A: Jack Kay was asked to come back to be in charge at Apotex. One year and one day after the murders, Jonathon Sherman and an Apotex executive ushered Kay out of the building. There’s no gold watch, no party. There’s mediation going on now because Kay was not offered anything after 35 years of service. It is the case that there is a lot of finger-pointing going on, as I report, where they initially blame Frank D’Angelo, then Jonathan says Jack Kay was involved. When Greenspan has written me, he says that my own sources, who I don’t identify, may be guilty as well. There’s a lot of finger-pointing.

Q: You asked everyone you interviewed “Where were you on the night of Dec. 13?” the night the Shermans are presumed to have been killed. When you went to ask the children, Greenspan asked you to go through him. He then said he couldn’t answer because he was “bound by police request.” Did you hear that from anyone else?

A: No, not at all. To the extent people had an alibi I would try to check it out. I have asked police on the witness stand if they ever asked people not to talk to the media, and they said “No.” [Donovan represents the Toronto Star in court in its bid to have documents about the case unsealed.]

Q: The Shermans were powerful figures entrenched in establishment Toronto, and establishment Canada. Family friends like Senator Linda Frum and Toronto mayor John Tory spoke to the police on behalf of the family. To what extent did the Shermans’ wealth affect your ability to report this story? I think for instance of how they successfully blocked access to what usually is public information, which is extraordinary.

A: It is so extraordinary. The Shermans have been able to block the will. I’m not even too sure how much is in that estate file. I’ve learned through the process, people who have private businesses can shield most of their assets from probate. It’s gone to the Supreme Court of Canada and they’re fighting hard to stop it. I have an interest in the Ford family and I went to court to see if the late mayor Rob Ford’s will had been filed. There was no problem. But the Sherman family wanted the will sealed because they said the family will be in danger if the information comes out. The police have said that won’t be the case.

The wealth really played into it. I had a hard time to have friends of Honey meet with me to tell one nice story. I said, “You’re treating them like the Kennedys, but the Kennedys got their story out so what is it about them?” Friends of Honey were afraid she would look bad—that she drinks diet Coke with lemon and could be harsh with people sometime. Once they felt more comfortable with me, the stories tumbled out.

Q: What about the details of the police investigation itself?

A: What I found very interesting is that when I had a detective on the stand in court—we go back every six months, that’s the deal we have—he said, “I can’t answer on that because the will and estate is embedded in our police documents.” That raises a lot of interesting scenarios for me because when I’ve interviewed people about the will it doesn’t seem that other people are beneficiaries. Maybe I’m wrong. Maybe that’s a key thing in the will that’s the answer. But the detective used the same word several times—it is imbedded throughout the ITO [authorization to obtain a search warrant]. To me that was a “Hey Martha” moment.

Q: You describe a major revelation during a court date last April, when you were trying to get documents unsealed and you asked Detective Dennis Kim on the stand if police had a theory of the case…

A: There was a long pause. He said: “Yes we do.” And I said: “What does your theory mean?” He said: “It’s an idea of what happened.” I asked: “Who are the suspects?” And the judge told me: “You can’t go further than that.”

Q: That was a eureka moment for you?

A: A huge eureka moment. Then I asked him again if he had a theory of the case in October and wondered if he would backtrack. He said “Yes.” I asked “Was it the same theory?” He said: “Yes.” I asked: “Is there a suspect?” He said: “I can’t tell you.” I asked: “Is there a person of interest?” He said: “I can’t tell you.” The most interesting thing that day was he revealed he got the Toronto police intelligence unit to go through a “voluminous”—his word—amount of data. And based on that they’re doing more production orders. And based on that, I think they’re close.

Q: We’ve been told the Sherman murder investigation has shrunk to one detective.

A: It’s bigger now. It started with 50 detectives, then down to one who produces production orders. Now they told me the original detective, Brandon Price, and another detective are involved on a daily basis.

Q: The Toronto Star‘s lawyer told you to go out and “solve the case.” In the book you don’t name anyone but clearly have some theories about who did it.

A: There were so many ‘out-there’ theories—that the murders were the result of a bad business deal, or the Mossad or the Clinton Foundation was behind it. I’ve arrived at the thinking that it’s not any of these theories. It’s somebody Barry Sherman knew who didn’t want him alive anymore and didn’t want Honey alive anymore. Years ago, Barry Sherman said, “If someone wants to take me out they could just shoot me.” That’s true. He would leave his office every night and get into his car. He would be easy to kill. Why kill him in the home? Why kill him with his wife? Why in the pool room? Who would know the schedule? The fact those bodies lay there for 36 hours tells me someone knew they wouldn’t be found.

Q: You write it would have to be someone familiar with the house, that it was personal, not professional.

A: I’ve spoken to people over the years about different types of homicide. And strangulation, that’s a very close, intimate thing. That’s different than hiring a hit man.

Q: You also write that you don’t think the killer or killers were professionals. One reason is the use of belts—one was taken from an upstairs bedroom. Organized criminals don’t look for their murder weapons at the scene.

A: I’ve not seen crime scene photos. But I was told belts were used. Barry was wearing a belt that morning, one Honey bought him at Canadian Tire. The other belt was from their bedroom, or my supposition is that was where the other belt was. I don’t think a foreign object was brought into the house to do the killing. Why the pool? Because it’s out of the way, because the tile floor can be cleaned up easier.

Q: Do you think this case will ever be solved?

A: I do. That’s one of the questions I ask Detective Kim. And I’m able to look at his answers four times over two years. This [latest] time he said: “The case is moving along well. It’s very active and we’re cautiously optimistic.” They seem very pleased with whatever this Toronto police intelligence report by civilian analysts told them. That appears to be a very big break in the case.

MORE ABOUT BARRY SHERMAN:

• Sherman family offers $10 million reward for information leading to arrest in murders
• Sherman family lawyer offers update on private murder investigation
• The other side of Barry Sherman
• The Barry and Honey Sherman murder investigation by the numbers