Police investigating Barry and Honey Sherman’s murders accepted odd limits sought by executors

The lone full-time detective on the case, Yim recently remarked that his job is never-ending.

“Sometimes it feels like you’re chopping the head off a mythical hydra and two more heads will grow back,” Yim recently told Justice David Porter of the Ontario Court of Justice, who next year will rule on whether the Toronto Star gets access to more of the police files detailing the Sherman case. “You do one (investigative) action and that action spurs two more actions.”

On that day one year ago, Yim carried with him a search warrant authorized the day before by Justice Leslie Pringle, one of her last acts before retiring from the bench. Pringle handled all of the Sherman warrants since day one.

When Yim arrived at the target office, the interchange took less than five minutes. A person handed over a computer storage device packed with 14,801 electronic files. This was not a true search. This was a handover agreed upon through advance discussion.

As a Toronto Star investigation shows, this is typical of how police have treated the Sherman business interests — carefully, with kid gloves. Members of the Sherman family, lawyers, and executors of the Sherman estate have determined what police can and cannot see in one of the highest-profile murder cases in Canadian history.

“It’s absolutely ridiculous,” said one investigator with knowledge of the case. “How on earth can this be solved without knowing absolutely everything?”

For example, way back at the start of the investigation, the Sherman camp quickly gave police the files on Barry’s deals with one businessman in particular, and Barry’s acrimonious dispute with four members of his own family.

Not so with Barry’s code-named offshore trusts and certain megadeals, including one valued at well over a billion dollars.

To this day, police do not have the full picture of Barry Sherman’s $10-billion empire.

For the past six years, the Star has been arguing in court for more scrutiny on a police investigation that went off the rails from day one — when Barry and Honey’s bodies were discovered. Toronto homicide detectives and a forensic pathologist initially theorized it was murder-suicide, until the Star published details of a second set of autopsies revealing that both Shermans had been tied at the wrists before they were killed, and thin ligatures similar to nylon zip ties were used to strangle them. No ties or bindings were found at the scene.

Now, Yim is mired in what police say is a “circumstantial” case — meaning there is no direct forensic or other evidence pointing to the identity of the killers.

This two-part series looks at how the police attacked the case: what they did, tried to do, and failed to do.

Today: Following the money

Mary Shechtman, Honey’s sister, headed to a Toronto police station on the evening of Dec. 15, 2017, the day the bodies were found.

“I was a mess, obviously, but I wanted to tell the police what I knew,” Shechtman recalls. She and her sister were best friends and Barry was like a brother.

Earlier that day, Shechtman was in Florida when she received the terrible news. It came in a phone call from the realtor who stumbled upon the couple’s corpses in their basement swimming-pool room, posed in a semi-seated position held upright by leather belts tied around their necks. Shechtman immediately chartered a plane home (a $20,000-plus expense to Sherman company Apotex that would quickly anger the Sherman children) and made it to Sherman daughter Alexandra’s house by the early evening.

Shechtman was there when homicide Det. Jeff Tavares arrived to speak with the family, but he provided barest of details and left quickly. Daughter Alexandra recalls being angry that Tavares “never even took off his coat.”

Shechtman decided to follow the detective to 33 Division, a North Toronto police station where the fledgling Sherman probe was centred. Tavares took Shechtman into an interview room and turned on a tape recorder. The whispers were starting that evening and Shechtman wanted police to know two things. First, murder-suicide was a ridiculous theory. Second, they needed to follow the money.

“Everyone wanted to get near Barry and Honey because of their wealth,” Shechtman told police, according to her interview statement.

While Shechtman did muse that religion might be a motive (she told the detective that Honey and Barry were strong supporters of Israel and Honey had recently attended a lecture “about stopping money from getting into Muslim fundamentalists’ hands”) she proceeded to give police a mini-tutorial on the dynamics of family and business associates.

She said the Shermans had wildly different parenting styles. Honey was the “mean one,” who was tough on the kids, wanting them to work hard. Barry lavished the children with money, beginning with $1 million when each turned 21, and much more to the two older children, Lauren and Jonathon, in later years.

Shechtman then gave police the first inkling they would have of the spiderweb of financial dealings they would have to unravel. The billionaire founder of Apotex was involved in a lot more than generic drugs. As one example (described in unsealed documents), she told them of Barry’s recently concluded multimillion-dollar arrangement with a young man named Andrew Liss, the former boyfriend of Jonathon.

That prompted police to reach out to Liss to get his side of the story.

In his interview, Liss told police that several years before, he and his then-boyfriend Jonathon had approached Barry with some business ideas. Barry liked one. A deal was struck where, as Liss later detailed to homicide detectives, Barry provided $50 million for Liss to build and sell homes. The caveat, according to Liss, was that Jonathon could not be involved (Barry wanted Jonathon to work at Apotex, Liss said).

The deal came crashing down in August 2016. Liss, as it turned out, knew nothing about building and selling homes. Barry stepped in and sold two homes that were being worked on by Liss. “I lost millions,” Barry told Liss.

For the next year, Barry paid Liss a “monthly stipend” (the police documents do not say how much). Those payments ended in July 2017. Liss and Jonathon had long since broken up (Jonathon had married Fred Mercure), but remained friends. Liss told police he felt “betrayed” at the way he was treated by Barry, having thought of the Sherman patriarch as a mentor and the Shermans as “family.” Honey, he told police, never liked him. Liss said Honey thought “he made Jonathon gay,” a sentiment Liss said was shared by his own mother.

Liss, who now lives in a countryside villa in Portugal and travels the world as “ThePamperedNomad” according to his Instagram page, did not respond to a request for an interview for this story. Previously, he told the Star, “Jon and I are on amicable terms, and like back then, we just want what’s best for each other.”

This story of a Barry Sherman deal is not unique in the partially unsealed police documents — now approaching 4,000 pages — filed in support of various search warrants and production orders.

There was the Barry-backed plan to get Apotex products into American nursing homes, an idea from an old business acquaintance. Then there was Sherman’s backing of Stephen Mernick in an apple juice venture (which then switched to a product designed to reduce cow flatulence, a contributor to greenhouse gas) that came crashing down.

As Alex Glasenberg, who ran Barry’s private investment firm Sherfam, told police: “There are 20 or 30 small companies that are investments with Sherfam.”

Given that police say in their search-warrant documents that there is a “financial” motive, Barry’s holdings were key to the probe. But figuring out just what Barry had — now and in the past — proved to be a big problem.

It began almost immediately after the Sherman bodies were discovered. As police do in a case of suspicious death, they seized Barry and Honey’s electronic devices from their home at Old Colony Rd. Two days later, they went to Barry’s office at Apotex and seized his desktop computer.

Before they could examine it, however, police received a sharply worded letter from Jessica Kimmel of the law firm Goodmans. She said that the security chief at Apotex had no authority to permit the desktop seizure, and that Goodmans, on behalf of Apotex and Sherfam, was asserting privilege. That led to a negotiation between lawyers from Ontario’s attorney general and Apotex, resulting in a very unusual protocol: Goodmans, on behalf of Apotex (owned, after their parents’ deaths, by the four Sherman children) would decide what police could and could not see.

Goodmans lawyers wrote that while they wanted to fully co-operate with the police investigation, they were concerned that if certain privileged information was released to police it “could result in significant financial harm to the company.”

With Barry and Honey gone, it fell to the executors of the Sherman estate to make these decisions. At the time, they were Glasenberg, Jonathon Sherman, Alexandra’s husband Brad Krawczyk, and Jack Kay, one of Barry’s best friends and his second in command at Apotex.

In the three months that followed the discovery of the bodies, the Sherman camp, including the executors and Sherman lawyers, made a decision on what police could get.

The Star does not know the entirety of the decisions made but has confirmed the following:

“Give them the D’Angelo stuff and the Winter stuff,” was how one insider recalled those deliberations, a reference to Barry’s investments with businessman Frank D’Angelo and Barry’s long-standing dispute with Kerry Winter and his siblings. The Winters had sued Barry for $1 billion, and just before the murders a judge ruled they had no case — ending the acrimonious lawsuit.

Even if there were elements that were legally privileged, it was decided that privilege would be waived and this information should be handed over to police, according to interviews and documents.

However, other information was held back, including some of the information related to Barry’s offshore holdings in the Bahamas and documents that detailed one of Barry’s biggest investments — in Edmonton businessman Darryl Katz’s empire. Barry had provided funding that helped Katz grow Rexall Drugs.

Tomorrow: Keeping Secrets