Murder, missteps and the ‘elephant in the room’ in the Barry and Honey Sherman case

Three thousand, four hundred and sixty-one pages. That's the size of the Toronto police search warrant file in the Barry and Honey Sherman murder investigation.

Compiled over some 50 months and submitted to a court, the documents detail elements of an investigation that has so far failed to solve the murders of billionaire generic drug titan Barry and his wife, Honey. Nearly every lead police have chased, every person they have interviewed, every scrap of relevant evidence collected is documented within those pages. It is, in essence, the road map through one of one of Canada's most challenging and most closely watched murder probes.

I've seen about half. I'm arguing in court on behalf of the Toronto Star and the public for the blackout text" to be removed from the rest, hoping it will shed more light on numerous missteps in the four-year-old case. I have also asked the court to unseal information related to what I termed the elephant in the room" - detailed statements by and about three people who by their own admission were probed in the case.

This legal battle is about the principle of open courts, and police accountability.

Justice Leslie Pringle of the Ontario Court of Justice, presiding over the Star's attempts to further unseal the files, has said the Star is providing an important service.

Mr. Donovan wishes to subject the police investigation to public scrutiny, to examine why it is taking so long and to expose if mistakes have been made. This is important and appropriate. Freedom of expression requires that the media be free to criticize and second-guess the police investigation," Pringle wrote in a decision May 25, 2021, one of six rulings she has made in the case. On two occasions, significant portions of the investigative files have been unsealed.

The Shermans were murdered in their Toronto home on Dec. 13, 2017. The documents that have been made public through this court process have allowed us to write about what went wrong in the probe, in the hope that mistakes will not be repeated in future investigations. There was the initial misdiagnosis of murder-suicide, and the crucial investigative time lost when the wrong questions were being asked. Most recently it helped me learn that what the police called their exhaustive canvass" of the neighbourhood missed a synagogue two blocks away on the Shermans' street.

The documents also told me that Toronto police believed almost from the start that the mysterious Walking Man" caught on video around the Sherman home was the killer - but did not seek help from the public until just recently.

Pringle is the judge who has viewed and approved all of these search warrant documents. As is typical with search warrants, she sealed them all, but has allowed some to be unsealed over the past year. Having heard my new arguments, and counter-arguments by Crown attorney Peter Scrutton, Pringle will rule on whether more can be unsealed sometime this spring.

I am not a lawyer. Yet from time to time I, and other Star journalists, go to court to argue cases where the public is prevented from seeing information filed in court. Sometimes our lawyers argue the cases, sometimes reporters do it. Regardless, the Star believes that the open court process is fundamental to our democracy. In the Sherman estate case at the Supreme Court of Canada last year, argued by Toronto Star lawyer Iris Fischer, the court agreed, reaffirming this principle.

When it comes to the Sherman search warrants, this has also involved me cross-examining the police detective who wants to keep everything sealed. I have done that every six months for the past four years with Det. Const. Dennis Yim of the Toronto homicide squad.

The documents are called ITOs." They are the affidavits (information to obtain" a search warrant or production order) that Yim has prepared - 12 separate ones so far - to convince Pringle to give police authority to conduct searches of bank and cellphone records, and some specific locations they have refused to reveal.

Pringle has been tough on the police at times. On several occasions she said no - telling detectives they need more grounds to be allowed to do something so invasive as checking a person's cellphone data, something police hoped would help them identify the Walking Man. Police hoped to catch one of about 300 people they considered a person of interest" communicating by cellphone to the Walking Man in the Sherman area the night of the murders. That search came up empty.

Our court hearings over the past four years were first in person, and now by Zoom. The judge, the Crown and the detective are completely professional and I have developed a great deal of respect for their patience as I take them line by line through more than 3,000 pages.

Some pages are now completely unsealed. Some are completely blacked out. Most have a bit of each - looks a bit like a partially completed crossword puzzle.

In our most recent hearing, a brand-new issue popped up. The court agreed to unseal a four-page section dealing with the Sherman estate - detailing how the four children split everything equally with their parents gone. I was told it appears in numerous" ITOs - but where it is located and the reason it is included remain sealed.

Here's my questioning of Det. Yim on what I believe is a key piece of information that should be unsealed.

Me: Is it normal in a homicide investigation to look first at people who are closest to a murder victim?"

Yim: Yes, I would say. I would say it's typical."

Follow the money, Barry and Honey's closest friends have told me throughout. Barry was a billionaire, and with him and Honey dead, his will left everything to their four children, each receiving their one-quarter share at age 35.

Me: I apologize in advance for being provocative with this next question but you've told us you look at people who are close first, you said that's typical in a murder investigation. Throughout this you've told the court that the estate is embedded in the investigation; we now see that there are parts of the estate that we've now seen unsealed that are in the investigation and you are being so secretive about it that you cannot tell me where (the estate passages) are. And we also see from what you have unsealed that there are only four beneficiaries, the four children of the Shermans."

I pause, watching the detective on camera. Yim is sitting in a plain room at police headquarters, answering my questions under oath.

Me: Is it just not completely obvious that you are investigating the four Sherman children, or one or a number of them?"

Yim: Well, all I can say is the evidence dictates where we go and the evidence or the information that we have dictates who we investigate."

I pressed Yim again, asking him if at any time in the investigation he has looked at any of the children. Previously, I had reminded him of stories the Star had published describing how Jonathon Sherman, Barry and Honey's son, had told me that one of his sisters had been saying that he was somehow involved in the murders.

Yim: I'm not going to discuss who is under investigation or who is not under investigation."

For the record, Jonathon told me in a lengthy interview a year ago that his sister Alexandra's belief that he was somehow involved in the murders is a ridiculous" notion.

One of the issues that has so fascinated me during this process is not just what has been revealed, but what has not been revealed and the lengths the police are going to maintain those seals.

The presence or absence, the positioning could be prejudicial to innocent persons or could identify persons of interest," Yim said.

Yim's comment that day is a frequent theme in these proceedings. There are two primary reasons he has for asking Pringle to maintain seals on certain portions of the file. He does not want anyone to know who are or have been persons of interest" (one rung below a suspect in police terminology). Nor does he want to prejudice" someone by revealing what others have said about them. As the Star has reported, Sherman family and friends have been pointing fingers in all directions for four years.

Here's one example of the sealing and unsealing of certain items. Recently, the court has unsealed numerous descriptions of the crime scene at Old Colony Road (the Sherman home) and photos of Barry's cluttered office, and their cars, Honey's in the driveway, Barry's in the underground garage. Also unsealed were security camera photos (from the Apotex video system in the lobby) of the three builders arriving at Barry's Apotex office for the 5 p.m. meeting the night the Shermans would be killed. For four years they kept sealed one line describing a photo of Barry, Honey and Prime Minister Justin Trudeau found in Barry's office - Yim provided no explanation for why that was sealed in the first place.

But to this day, police refuse to release images of Barry and Honey as they left Apotex to go home that evening. Police say they do not want anyone to know what the Shermans were wearing because they want any future witnesses" to be untainted by information in the public domain. Yim says one day a witness" might come forward and say they saw one of the Shermans that night and police want to compare their description to what the Shermans were wearing to determine if the witness actually saw them.

I countered that it is generally known they were wearing dark coats. (Honey had a blue down vest on under her coat.) Besides, I said, the quality of the photos of the builders in the Apotex lobby is so poor that you can make out their faces but not much else.

Also still under seal are video stills captured by a home security camera across the road from the Shermans' house, which Yim has confirmed show Barry and Honey arriving home at night in their respective vehicles.

Yim and Crown attorney Peter Scrutton both say that to unseal those photos would reveal the Shermans' direction of travel" that evening. In a phrase I borrowed from one of my longtime lawyers at the Star, Bert Bruser, I told the court that's nonsensical." Unless they are trying to keep the photo sealed because it shows someone following the Shermans - or in the car with the Shermans - I argued that they should be released. Yim said again that the presence or absence" of something in a photo is key to their case, and stopped there.

That small issue is just one of hundreds of points Pringle will rule on this spring.

The Star is trying to scrutinize the investigation to see if detectives did their due diligence at every step. While some points may be minor, we have argued that we need to see the complete file to bring more scrutiny to the case.

For example, one section of the ITO states how an extensive canvass of the neighbourhood has failed to reveal any persons who could provide compelling information in relation to the deaths of the Shermans." I heard through a friend that a choir was practising the night of the murders at Temple Emanu-El, a synagogue on the Shermans' street, two blocks from their home. I spoke to the executive director, the rabbi and a choir member who was there Wednesday, Dec. 13, 2017. The police never spoke to any of them, nor did they ask for video.

This is roughly in the area where the Walking Man was seen, and early on, Honey's sister was telling police the killings could have been a religious hate crime." Should police not have visited the synagogue to see if they had heard or seen something? Now, none of the three people I spoke to recalled seeing anything of importance, but there were many others that night who police could have spoken to. The point I made in court was, just how extensive" was this canvass?

Yim's frequent comment about the presence or absence" of information in his ITOs got me thinking. Half of the 3,461 pages are still redacted - sometimes full pages are blacked out, including one redaction of dozens of pages headed: New Information. What might be in there?

And why are most interview statements unsealed, but a handful sealed? Why, for example, is there not one single visible reference to Kerry Winter, Barry's cousin and nemesis for two decades. This was the man who talked openly in the media (the Toronto Star, CBC's The Fifth Estate," the Daily Mail) about his fantasy of murdering Barry Sherman, cutting his head off and rolling it down the sidewalk at Apotex.

Winter and his siblings had a decades-long, acrimonious fight with Barry. He had given the four of them $25 million over the years to support their businesses, but then the siblings sued Barry, claiming they deserved a $1-billion chunk of Apotex, arguing unsuccessfully in court that it was their father whose business set Barry on his meteoric rise. In fact, Barry won a $300,000 cost award against the siblings just before the murders.

Smoke and mirrors," Winter said recently, when I told him his name was nowhere to be found in the unsealed files, and that I believed there was a great deal about him and his case in the ITOs. Winter still believes Barry snapped and the deaths were a murder-suicide.

In my argument before Pringle, I referred to this as one of several elephants in the room" - Winter's animosity to Barry was so public, how could the police not have looked into it? I suggested that redacting everything related to him was unfair and that it might make it seem as though he is a suspect because any reasonable person would expect this name and his statement to police to be in the ITOs.

Remember, these ITOs were filed in court to obtain permission to track the movements of and communication from hundreds of people who knew the Shermans.

I pointed out in court that Winter spoke openly in the media in early 2018 of how lead investigator Det. Sgt. Brandon Price of Toronto homicide interviewed him, how Winter provided his alibi for the night and let police look at his phone. Winter said he also gave his viewpoints on the case and his own belief that it was a murder-suicide.

I also know (because they told me in interviews) that numerous Sherman family members and friends told police about the Winter lawsuit and suggested they check into him. I argued in court that it is my belief that a lot of what remains sealed relates to Winter and two other people. The only small hint of Kerry Winter in the ITOs is a link police have included to a Bloomberg article about Winter and his battle with Sherman in which Winter is quoted saying, I had plenty of opportunity - and motive - to kill Barry." The link is there, but police have sealed the commentary describing why they believe that article is important enough to include it in an ITO.

In a similar fashion, the witness statement given by Barry Sherman's friend and business associate Frank D'Angelo is nowhere to be found. As I told court, D'Angelo also gave a statement to Price early in the investigation. Like the Winter statement, I told court it was my belief D'Angelo's statement is under seal - the second elephant in the room."

Very interesting," D'Angelo says. He says he misses his great friend" every day and remains hopeful police will solve the case.

Unlike Winter, D'Angelo's name has recently been unsealed in one area, a minor comment about one of the businesses he and Barry were involved in. (Barry financially backed D'Angelo for decades.) In another spot in the ITO, there is a newly unsealed statement by Barry's second in command, Jack Kay, who in describing plans for the Sherman funeral tells police the Sherman family will do a private and public funeral service and the children told Jack to make sure that [redacted] does not show up." I pointed out to court that sealing the name of the person made no sense because it has been reported publicly that the Sherman children, particularly Jonathon, did not want D'Angelo at the funeral and asked Kay to deliver the message. D'Angelo confirms this.

As the Star has reported, Barry Sherman was very close with D'Angelo - loved his work ethic, according to Kay. But Sherman's son, Jonathon, often had words with his father (detailed in emails the Star has published), asking him to stop funding D'Angelo's businesses, which Barry refused to do.

I told court that the third elephant in the room" was information related to Jonathon. Parts of Jonathon's two statements to police remain sealed, along with what I told court I believe were statements others have made about him. In my interview with Jonathon a year ago, he said he hopes police looked into him, and all of the Sherman family.

I argued that given that Jonathon, D'Angelo and Winter have spoken openly about their statements to police, and suspicions about them, there is no point in keeping everything sealed. Secrecy, I argued, makes it seem like police have not cleared them.

In the Sherman murder case, and indeed these documents, the elephant in the room is that these three individuals have been considered by the police as persons of interest and we know this because they have spoken publicly about this matter, including providing their alibi for the evening in question," I argued.

Crown attorney Scrutton, who is arguing to keep the remainder of the file sealed, told Pringle:

The Crown disagrees with Mr. Donovan's submissions about the relevance of media coverage speculating on the motives of Kerry Winter, Frank D'Angelo and Jonathan Sherman to commit these crimes. The Crown submits that this does not militate in favour of unsealing in this context."

Justice Pringle will rule on the case in the next few months.

Kevin Donovan can be reached at kdonovan@thestar.ca or 416-312-3503