Today, a year after the founder of generic drug giant Apotex and his wife were slain, the revelation that the financial affairs of one of Canada’s wealthiest couples were not in order when they died is just one of a string of mysteries in the case.

A fear of “kidnapping and violence” prompted the Sherman family to seek — and be granted — a court order completely sealing information on the couple’s estate, including the amount and distribution of assets. The lack of a will by Honey Sherman is just one part of that.

“We don’t know who the beneficiaries are, if there is a will,” Sherman estate lawyer Timothy Youdan told a court hearing in July. “We don’t know if there is no will.” To proceed with the administration of the couple’s estate, Youdan filed a document asking for the “appointment of estate trustee without a will in the estate of Honey Sherman.”

What effect, if any, the lack of a will in Honey Sherman’s case is having on the disposition of one of Canada’s biggest shared personal estates — estimated at $5 billion — is unknown, due to the rare court order, which seals what would normally be a public court file.

In his first of two sealing orders, Ontario Superior Court Justice Sean Dunphy wrote in June that the file contains “confidential materials of potential relevance to the police investigation.” Whether the Toronto police have been provided this information, neither the police or the family will say.

When Dunphy later issued a two-year blanket seal, he said he did so to protect the “privacy and dignity” of the both the late Sherman couple and their loved ones. Dunphy also said he was doing it out of concern that the killers, who have never been caught, would harm someone else. During a hearing where the Star sought access to all or parts of the court file, the Sherman family lawyer warned that the beneficiaries and trustees of their estates could be vulnerable to “violence and kidnapping” if any information in the files was released.

“The willingness of the perpetrator(s) of the crimes to resort to extreme violence to pursue whatever motive existed has been amply demonstrated,” Dunphy said in his August ruling. “The risk of harm is foreseeable and the foreseeable harm is grave.”

Barry, 75, and Honey, 72, were found strangled on Dec. 15, 2017, each with a leather belt looped around their neck and tied to a metre-high railing around their basement pool. According to forensics sources with knowledge of the case, the couple most likely died late on Dec. 13 or early on Dec. 14. While police say the investigation is ongoing, the Star has learned that as of this fall there was only one full-time officer on the case.

A Toronto Star probe has found serious failings with the police investigation.

Recently, the Sherman’s four children announced a $10-million reward for information leading to the “apprehension and prosecution” of the killer or killers. In an unusual step, the family has directed tips to its private investigation team, not the Toronto police homicide squad — an indication of the fractured relationship that has existed since police initially pursued the case as a murder-suicide.

At the cemetery where their parents are buried, the Sherman children recently unveiled a grave marker that reflects the uncertainty of the ongoing investigation — rather than a specific date, it simply notes their deaths as having occurred in “December 2017.”

Although the Sherman estate file is sealed, the Star has determined some information by interviewing sources connected to both the case and the Sherman family. The sources are not named in this story because they were not authorized to provide this information.

While Honey appears not to have had a will, Barry had both a “primary” and a “secondary” will. In Ontario, people who own a private business often have two wills. The primary will includes such things as real estate, vehicles and publicly traded shares — holdings that typically go to “probate” and for which an estate administration tax must be paid to the government. No estate tax has to be paid on anything left in secondary wills, which typically house shares in private companies. In the Sherman case, his company Apotex is privately held, mostly by the Shermans.

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One of the intricacies of estate law is the “simultaneous death” situation, in which spouses die at roughly the same time (car and airplane accidents being the most common examples). In the Sherman case, both were last seen alive on the evening of Dec. 13, 2017: Honey left a meeting at Apotex headquarters with her husband and the architects of a planned Forest Hill home around 6:30 p.m., and Barry left his office at 8:30 p.m. One scenario under investigation by police, sources say, is that Honey arrived home shortly after 7 p.m. and was surprised by an attacker or attackers; the same happened to Barry when he arrived home later, around 9 p.m.

Without access to any of the material filed in court, it is impossible to determine how the Sherman trustees are dealing with the combined estate in the absence of a will from Honey. Four trustees are administering various parts of the estate. Two are family members, and two are businessmen who worked for Barry Sherman for decades.

Sources have told the Star that Barry’s will left everything to Honey if he died first; if she predeceased him, it divided the estimated $5-billion estate and control of Apotex between their four children, aged 28 to 43.

In the hearing before Dunphy, Youdan said simply, “We do not know the order of death.” Due to the sealed file, the Star lacks the information to understand the relevance of this statement. However, death order is significant because, if Barry died first, his estate would flow to Honey, whose lack of a will could complicate how it is dealt with.

(In an email interview this week, Youdan said he was referring in court only “to the facts as known in the public sphere.” He said he was not revealing details about the order of death, the status of wills, or whether or not an individual had a will. He did not elaborate.)

Further complicating the estate situation is that, soon after the deaths, at least one person claimed to be due a sizable payout that was allegedly promised by Honey, according to sources close to the Sherman family. The Star is not identifying this person, who could not immediately be reached for comment.

In court, Dunphy noted that the bulk of the Sherman fortune was dealt with in Barry Sherman’s secondary will. The judge did not quantify the value of the estate in Barry’s primary will, but commented that “for people in that snack bracket, it is walking-around money.”

It is unusual for an estate matter, once filed in court, to be sealed.

As part of its investigation into the Sherman case, the Star has been seeking access to information held in a variety of court files. For example, the Star has perused civil files where Barry Sherman was in litigation with individuals over business deals, and attempted to access search warrant files to scrutinize the police investigation.

In the case of the Shermans’ estate, the Star sought information that would normally be on the public record. But when the Star asked to see the file at a University Avenue courthouse, staff said it was sealed and the Star would need to make an application to try and unseal the documents.

From some initial documents that remain public, the Star has determined that as soon as the Sherman family lawyers filed their application to formally appoint the four individuals as trustees, they asked for the file to be sealed. Dunphy sealed it with a “protective order,” writing in his endorsement that the file contained information “of potential relevance to the police investigation.”

The Star went to court to challenge the sealing order, arguing that courts in Canada are presumptively open and that there was no reason to seal the estate files.

The Star further argued that any harms anticipated by revealing information in the file, such as the amount of money to be divided and who would receive it, were “speculative” and that the names of the four Sherman children and the estate trustees were well known already.

The Sherman family countered with references to an affidavit within the sealed file by a person referred to only as “AB,” who describes the ills that will befall individuals if the file is made public.

AB wrote, “There is a legitimate and ongoing risk to the personal safety and security of (the estate trustees and beneficiaries), including risks of violence and kidnapping, in circumstances where the identity and motivation of the perpetrator(s) of the murders remains a mystery.”

In the court hearing, Dunphy acknowledged that the Sherman family’s “AB” affidavit “made no reference to receipt of warnings or opinions regarding the degree of risk from Toronto Police Service.” Still, Dunphy said that while the concern by the family of harm was “necessarily speculative,” he found that it was “nevertheless reasonable.”

Dunphy did say in his ruling that the “open court principle is a fundamental one.” He was asked in court by the Star if he would consider revealing some but not all of the information in the file, perhaps redacting addresses and telephone numbers of individuals but keeping financial details in. Dunphy said he considered it but found there was “no meaningful part” of the Sherman estate files that could be disclosed.

The Star is appealing.

Toronto police have said their murder investigation is ongoing, but declined to answer questions about its progress.

Over the past year, the Star has found a series of problems with the case, including:

• DNA was not taken from some innocent parties, who were in the Sherman home earlier on the day the couple died, for at least eight months. This is typically done in relation to a crime scene to exclude innocent parties and focus on potential suspects.

• CCTV footage of areas on the outside of Apotex were not viewed by police until at least a month after the murders.

• Police had made a preliminary determination of murder-suicide in the case and did not investigate it as a targeted double homicide until a Star story on Jan. 19 revealed that the family’s hired pathologist had ruled it so. Toronto police had been invited to attend the second autopsies, which were performed by Dr. David Chiasson, but declined.

Kevin Donovan is the Star’s chief investigative reporter based in Toronto. Reach him by email at kdonovan@thestar.ca or follow him on Twitter: @_kevindonovan