On the other is Jonathon’s sister Alexandra, along with her former husband, and a money manager Barry trusted for years to handle the fortune he built up as founder of generic drug giant Apotex.

Woollcombe, Jonathon’s nominee, is asking Ontario’s Superior Court to make changes in the oversight of the Sherman fortune that he says is needed to protect those assets. Meanwhile, Jonathon has asked the court in a separate action to remove two Sherman board members he has accused of breach of trust. Those two board members are also executives of Barry’s holding companies, handpicked by Barry before he and his wife Honey were murdered in 2017.

Unless a settlement is reached before May 25, the financial affairs and squabbles of the notoriously secretive Sherman family will be aired in a Toronto courtroom for the first time.

Justice Sean Dunphy, the judge who will preside over the case, has dealt with the Sherman family before. Back in 2018, when the Sherman estate was going through probate, he agreed to their request to seal the entire file from public view. His ruling was challenged by the Star, and overturned by the Ontario Court of Appeal. The Supreme Court of Canada upheld that decision in 2021, reaffirming the rule of court openness, a decision that is cited frequently in Canadian courts. 

Earlier this year, Dunphy set the table for the new dispute in a ruling that touched on the animosity between the four heirs to the Sherman fortune.

“The tragic murder of Honey and Barry Sherman in 2017 thrust upon their heirs the responsibility of dealing with an indescribable personal tragedy while also attempting to sort through the complex personal and business issues that managing the resulting estate gave rise to,” Dunphy wrote in a February ruling.

“The fact that (the four Sherman children’s) relationship with each other has not been seamlessly harmonious since then is unfortunate, but not at all surprising,” Dunphy said. He told lawyers for the Sherman children and other parties (there are 24 lawyers involved from some of Toronto’s most prestigious law firms) to get prepared for an open court hearing.

It promises to be a rare look behind the curtain of a private company. 

The seeds of this dispute trace back to a time before Barry, 75, and Honey, 70, were found murdered next to their underground pool.

Barry, who often told his late friend Jack Kay that he would live to 120, did not do as much estate planning as his friends wanted him to do.

When he died, Barry left a relatively simple will, leaving his fortune to Honey if he died first. No will for Honey has ever surfaced, although she told a close friend shortly before she was murdered that she had just updated her will.

On Honey’s passing, Barry’s will stipulates that their estate was to be equally divided between their four children — Lauren, Jonathon, Alexandra and Kaelen — when they had reached their 35th birthday. In 2017, Lauren was already over 35, Jonathon was just turning 35, and Alexandra and Kaelen were not yet that age. All four are 35 as of last year. There is no public record of how much they have each received so far.

Sherman was worth billions — estimates range from $4.7 billion to $10 billion, with some of it offshore in the Bahamas. To oversee his fortune, Sherman appointed four people as trustees or executors to his estate — his son Jonathon, Jack Kay, money manager Alex Glasenberg (who was and is the CEO of the Sherman trusts) and Bradley Krawczyk, who at the time was married to his daughter Alexandra. Originally, his three daughters were also trustees, but Barry changed that less than a year before his death.

Then the murders. On a wintry December day in 2017, persons unknown strangled Barry and Honey and posed them in their basement swimming pool room in a seated position on the pool deck. Toronto police say they have “many” persons of interest but are “playing blind” as to where they are in the case.

In emails exchanged between Jonathon and Barry six weeks prior to the murders, Jonathon told his father that he was “the heir apparent.” To which Barry replied, “You are my son and an heir to the empire.”

In the first year following the Sherman murders, Jonathon took charge at Apotex. A year and a day following the murders, he marched his father’s second in command, Jack Kay, out of the Apotex offices. Kay, who died last year, eventually received a multi-million dollar payout to settle what was essentially a wrongful dismissal dispute. Kay had worked for Barry for 35 years. 

As the Star has reported, Jonathon told his sisters that he thought it would be best if he handled their financial affairs, and the financial affairs of the Sherman fortune — the largest portion being Apotex, the generic pharmaceutical company Barry founded in the early 1970s. His sisters fought back against that, sister Alexandra has told the Star. 

Between 2018 and 2021, lawyers’ letters flew back and forth between the siblings. Compounding this acrimony was sister Alexandra’s accusation that Jonathon was somehow involved in the murders, according to Jonathon in an interview with the Star. Jonathon has denied any involvement in the murders. He has personally added a promise of $25 million to the family’s original $10 million reward to catch the killer, and hired a New York lawyer to look for clues. 

The simmering financial dispute between the siblings came to a head in 2021. That’s when all four Sherman siblings agreed to create a seven-person board of directors to oversee the business empire Barry left behind, called Sherfam for “Sherman Family”. Each Sherman sibling nominated one person for the board; Glasenberg and Krawczyk joined them. (Both men have management positions at Sherfam.) 

The four siblings also agreed to appoint an independent chair as the seventh member, choosing Barry Reiter, described in court pleadings as “an experienced director and recognized corporate governance expert.”

The business affairs of Sherfam proceeded relatively smoothly for a few years. The family sold Apotex to an American company, leaving real estate and business investments for the board to manage. A private company, Sherfam is not required to identify any of its holdings to the public. 

What happened next has been pieced together by the Star from legal actions filed by numerous parties. The lawyers involved declined to give interviews, saying the matter is before the court.

In the spring of 2025, what had been a simmering dispute between Jonathon and the pair of Krawczyk and Glasenberg bubbled up. According to pleadings filed by Jonathon, Krawczyk and Glasenberg were trying to kick him out of the largest trust under the umbrella of the seven-person board. A few months later, in July, Jonathon launched his own legal attack, asking a court to remove Krawczyk and Glasenberg from that same trust, citing “breach of trust” and telling the court that they were not acting in “the best interests of the beneficiaries.”

Those competing accusations went nowhere in court. But then a new salvo was fired, this time by Woollcombe, Jonathon’s nominee to the seven-person board. In a legal action begun last summer, Woollcombe accused the Sherman trusts of “oppressive” conduct against him as a board member, saying that certain actions they had taken prevented him from protecting the Sherman assets. A lawyer himself, Woollcombe describes himself as an “experienced director, business advisor and corporate lawyer.” He declined to comment to the Star. 

Woollcombe’s beef, according to court filings, was that a 4-2 majority of the board refused to renew the term of the independent chair, Reiter.

That made Woollcombe concerned that the board would not be able to provide “oversight regarding investments of more than $2 billion recently made or agreed to be made at the direction of the board.” What those investments are, the documents don’t say.

Woollcombe said he needs the assistance of the court to help him continue to act as a director (there is no hint in the documents that he is to be removed), and if that doesn’t happen, there will be “significant harm” to the Sherfam companies. He wants the court to either reinstate Reiter or appoint a new “independent chair,” according to court filings. Woollcombe also takes issue with the longtime Sherman family law firm, Davies Ward Phillips and Vineberg LLP, continuing to provide advice to the Sherman companies’ board. He says they are in a conflict of interest because the firm is also the lawyer of record for Barry and Honey’s estate. Davies has not responded to the Star’s request for comment.

In the only personal allegation levelled in Woollcombe’s pleadings, he has accused fellow board member Glasenberg of carrying out a “scorched-earth litigation strategy” against him, including threats of lawsuits. 

Glasenberg’s lawyer Chris Paliare told the Star this week that his client denies Woollcombe’s allegations, calling them “an extension of Jonathon Sherman’s unfounded allegations made against his fellow trustees” in the suit Jonathon filed last year.

It will be up to Dunphy to sort this out. Dunphy has issued marching orders to the 24 lawyers who are on record in this amalgamated case. They are to conduct all cross-examinations required, exchange documents, and make sure they are ready for a May 25 hearing in his courtroom. 

Dunphy, with a mind to concerns raised in various pleadings about the secrecy of Sherman company dealings, has told all lawyers to be mindful of the Supreme Court of Canada’s open-court ruling in the Star’s Sherman estate challenge.

In a thoughtful comment in his most recent ruling, Dunphy said that this current case is a “symptom and not a cause of the underlying disputes between the beneficiaries of the estate.”

Meanwhile, this December will mark nine years since the Sherman murders. With “many” persons of interest still in the mix, the lone detective working half-time on the case (with the help of AI) says it is impossible for him to say exactly where he is in the investigation. The detective has told the court that his most recent task is reviewing 14,801 electronic files seized in a search warrant in 2022. The Star has determined these are Barry Sherman’s business records seized from the Sherfam offices.

Based on information provided to the court by the detective on how long it takes him to review and categorize each document, the Star estimates he will be finished in just over 30 years.