Barry and Honey Sherman murder probe was kept away from ties to offshore banking and to Edmonton Oilers’ owner

Just before the 2017 murders, Winter and his siblings lost a billion-dollar lawsuit against Sherman and were ordered to pay $300,000 in legal costs. Soon after the Shermans’ bodies were discovered, Winter famously told the Star and media around the world that he had long fantasized about cutting off Barry’s head and rolling it down the sidewalk of Apotex, Barry’s company.

D’Angelo, known for making movies and beer backed by Sherman, was hated by Sherman son Jonathon and others in the Sherman circle, according to family emails obtained by the Star. So despised that the Sherman children asked that D’Angelo not attend the funeral. Jonathon has told the Star he believes D’Angelo was blowing millions of dollars and he relayed his suspicions to police that D’Angelo was involved in the murders.

Both Winter and D’Angelo know that the finger was pointed at them and that all of the information relating to their dealings with Barry has been turned over to the police. Both have been interviewed by police and provided alibis. Both say they had nothing to do with the murders.

“Barry was the closest thing to a brother I ever had,” said D’Angelo. “He helped me achieve all of my dreams.”

Winter said he had nothing to do with the murders — in fact, he believes that the police theory at the start was correct, and that Barry murdered Honey and took his own life. “It’s a coverup,” he has said.

Both men were summoned by homicide detectives in early 2018 and gave lengthy interviews to police. Their statements remain sealed by court order, though both have told the Star they are in favour of them being unsealed.

“I have nothing to hide,” says D’Angelo. During decades of work together, Barry funded numerous movies D’Angelo made, two restaurants and a venture into beer brewing. With Barry gone, and son Jonathon in charge, D’Angelo’s funding was cut off.

Winter was the son of Barry’s uncle, Lou Winter, who gave Barry his start in generic drugs in the 1960s. Kerry Winter and his siblings alleged in various court actions that Barry owed them one-fifth of the value of Apotex — a claim that a court dismissed shortly before the murders.

As the Star reported yesterday, the four executors of Barry and Honey Sherman’s estates met in 2018 to decide what homicide detectives could see and what documents or electronic files the Sherman camp would claim was legally privileged. Legal privilege applies to documents or communication related to legal advice, often in connection with litigation. In murder cases, this issue rarely comes up, but it did in the Sherman probe due to Barry’s extensive business dealings.

A protocol was hammered out between Sherman lawyers and Ontario government lawyers. Police seized the information from Barry’s devices and office — then the Sherman lawyers and executors made the decisions. One internal document shows that a decision was quickly made to “waive any privileges” on the D’Angelo documents found in Barry’s office.

It appears most of the information in the Sherman files involving the Winters siblings was handed over to police. There was discussion by the Sherman camp over one batch of documents but a decision was made to “waive privilege.”

Veteran homicide detectives (not involved in the Sherman case) said that while the issue of legal privilege does crop up occasionally, what happened in the Sherman case was “well beyond the norm.”

The Star, which has been investigating the case for six years, has determined that there remain vast amounts of Barry’s empire that police have never seen — along with numerous email chains between Barry and Honey, their family, and others — some of them revealing deep disputes between children and parents.

A new search warrant police obtained in late 2022 may shed at least some light on Barry’s financial dealings. Det.-Const. Dennis Yim is in the midst of reviewing more than 14,000 electronic files police obtained at an unknown address.

However, the Star has determined there is still a lot of information police do not have. That information may have nothing to do with the case at all, but former homicide investigators interviewed say that police need the full picture.

One batch of documents police have never seen relates to one of Barry’s biggest investments — with Darryl Katz of Edmonton. Katz is well known as the owner of the Edmonton Oilers and, until 2016, Rexall Drugs.

Documents the Star has seen show Barry had a significant investment (more than 50 per cent) in the Katz drug empire. Katz sold Rexall to an American company, McKesson, in 2016 for about $3 billion, and Barry’s investment was paid back.

All information related to this transaction has been kept from police, according to sources and documents. The Sherman executors determined that it was all “privileged.”

Reached by the Star, Katz said he did not want to comment on the case, beyond saying that “Barry was a good friend of mine and I greatly appreciate the work you have done regarding the murders. The matter must be solved.”

Asked about Barry’s investment in the Katz companies, Katz said “the information you have been given about my business relationship with Barry is incorrect.” He did not specify what was incorrect. The Star has interviewed numerous leaders in the Canadian pharmaceutical world who all say it is an “open secret” that Barry Sherman invested with Katz — though this information has been kept from the public domain for years.

The Star has learned that another section of Barry’s financial life that police have not penetrated is his many offshore holdings in the Bahamas. Trusts holding Barry’s money in the Bahamas include Wasanda Enterprises and the Harvey Rubenstein Settlement, the latter one Barry cheekily named using the real name of a Toronto stockbroker who Barry said defrauded him back in his early days.

Sherman sources say that Barry used his Bahamian cash to pay executive bonuses, fund real-estate deals and invest in new companies. It’s unclear if taxes were paid on what amounts to, sources say, about $2 billion in funds sheltered in tax havens like the Bahamas. Both of the above Bahamian trusts are listed in either the Panama Papers or the Pandora Papers, two major dumps of offshore holding records made public by the International Consortium of Investigative Journalists.

Documents and sources indicate that some minor files related to the Rubenstein trust were handed over to the police, but the bulk of the trust information remains housed in a nondescript brown brick building just north of Toronto — the headquarters of Sherfam, the Sherman family’s holding company. The building beside it houses Hour Investments, Sherman son Jonathon’s personal holding company.

Sherfam, to this day, is run by Alex Glasenberg, the banker hand-picked by Barry years ago to manage his fortune.

The Star has asked Glasenberg if the most recent Toronto Police search warrant in the Sherman case (which retrieved more than 14,000 business records) was served on Sherfam. Glasenberg has not responded to the Star’s questions.

What is clear from the Star’s comparison of various documents in the Sherman case is that homicide detectives searching for the truth have run up against numerous brick walls.

In just one example, Glasenberg told detectives during his interview on Dec. 29, 2017 that, to the best of his knowledge, “Barry does not owe anyone any money.”

Yet just two months before the murders, Glasenberg sent a stiffly worded email to Barry warning him that his company was in dire straits due to Barry’s financial decisions. Glasenberg told Barry that his behaviour would cause the bank to “call the loan immediately.” Apotex, he said, needed to address its problems. “The company is insolvent and will have a going concern note.”

Barry responded there was no need to worry about Apotex as, through Sherfam, he had plenty of cash to cover any deficit. Plus, Barry said, he was expecting to win several lawsuits over the next few years, with payouts of up to $1 billion.

Meanwhile, the homicide probe continues. In addition to the initial finger-pointing by the Sherman family, the Star has learned from its ongoing battles in court about the murder case that many of the 250 people interviewed by police have given at least five suggested “persons of interest” to detectives. While there has certainly been some overlap, it appears that detectives have a list of dozens and dozens of potential suspects.

During cross-examination as part of the Star’s challenge of the search warrant sealing orders, Det.-Const. Yim said that to this day police have not “cleared” a single individual from this list.

Tom Curry, a lawyer representing Jonathon Sherman, contacted the Star Thursday night regarding questions the Star had sent.

“Jonathon Sherman mourns the loss of his parents on the sixth anniversary of their deaths and misses them dearly. He has and always will be fully cooperative and transparent with the Toronto Police Service’s investigation of their murders and will continue to support their efforts to find the person, or persons, responsible for these terrible crimes,” Curry said.

Meanwhile, Chantelle Cseh, a lawyer speaking on behalf of “the Estate Trustees” told the Star Thursday that “the Estate Trustees have at all times cooperated fully with the TPS in its investigation” and that, to the trustees’ knowledge, “there are no pending or outstanding requests for information from the (Toronto Police) that remain unanswered, in whole or in part. Neither Cseh or the trustees responded to specific questions about information the Star’s sources say has not been provided to police.