Barry Sherman’s son says his father asked him to repay tens of millions of dollars, two weeks before murders, but Barry was ‘all in’ with son’s business

The road into Jonathon Sherman's 100-acre compound winds through a forest. A yellow smiley face tacked to a tree warns visitors that cameras are watching. Afraid for his life following the 2017 killings of his parents, Barry and Honey Sherman, Jonathon also employs a permanent detail of security guards who live in one of the houses on the rolling property.

Come alone, Jonathon told me.

In a back and forth email exchange in December leading up to our interview, the 37-year old businessman explained his desire to provide context" to his father's request - two weeks before his death - that Jonathon and business partner Adam Paulin pay back between $50 million and $60 million that Barry had loaned them. His father, Jonathon said, was in a difficult financial situation but vowed to restart the flow of cash down the road.

I'm not going to kill my dad because he needs $50 million to get through a crisis," Jonathon will later say over the course of a five-hour chat, confronting suggestions by some that he was involved.

Stepping out of my car on a snowy day in late December I see nobody about. It's a gloomy afternoon, but there are no lights on in the log cabin where the road dead ends. To one side, a long, rectangular garage. The metallic rasp of a door latch breaks the silence and a man steps out, wearing jeans, a hoodie and a coat.

I had never met Jonathon Sherman before, but I recognize him from the video of his eulogy at his mother and father's funeral.

Just working on one of my COVID projects," Sherman says, then retraces his steps. I follow. Inside the garage I pass a silver Tesla, and in the centre of the workspace a beautiful wooden canoe, upside down on a stand. Sherman explains he has never built anything like this before. He shows me long, thin tongue and groove slats that he has glued, one by one, framing the elegantly shaped boat. Next he will sand the joints, and apply multiple coats of fibreglass. It is for his cottage and marina on Chandos Lake northeast of Peterborough where, as I reported some time ago, he once told his father he and Paulin wanted $150 million to buy one quarter of the cottages. That was the same time that Jonathon, angry with how his father was spending money on other enterprises, suggested to his three sisters that Barry was incompetent and unable to manage the family fortune he had built.

I walk around the chilly workshop. In a box there are clay target discs for another of his passions, skeet shooting. Sherman says he is a collector, has 15 guns - many of them antique, lever action cowboy" classics - and a shooting range in the forest.

It is noon on Dec. 19, 2020, just over three years from the day that Barry, 75, and Honey, 70, were found dead of ligature neck compression" in their north Toronto home. Toronto police homicide detectives say the case is active and ongoing and that they have numerous persons of interest and a theory" of what happened. Who those people are, and what the theory is, police will not say.

I have been trying to speak to Jonathon Sherman for a long time and he has granted me this opportunity because, he says, he is tired of people talking behind his back, speculating that he had something to do with the killings. Most vexing to him, he says, is that his sister Alex thinks he was involved, which has created a rift he believes will never heal.

I want to arm you with the truth," he says. Over the afternoon he will open up about many issues, promising me he will never be inconsistent."

Sherman motions to two black folding chairs, two metres apart, between the Tesla and the canoe. We sit. Sherman has referred to himself in an email as the heir apparent" to his father's fortune, estimated to be worth between $5 billion and $10 billion. Yet the power tools lying around are not even remotely top of the line. The Tesla is a 2013 model. It bothered him, he said, when I wrote in my book on the Sherman killings that he owned a high-end electric vehicle and flew first class. He said he purchased the car used, years ago, because I hate paying for gas." As to flights, he said that he flies economy in North America, business class internationally, similar to the rest of his family. He maintains he is as frugal as was his thrifty father, who drove rusty old cars and ate at Swiss Chalet.

We are in this garage because in early December I had reached out with new questions about his financial relationship with his father leading up to the killings. I had been told by several sources that in late 2017, Barry Sherman's company, the generic drug maker Apotex, was experiencing financial difficulties. That was confirmed by a recent release of police search warrant documents following a court challenge by the Toronto Star, which revealed Apotex had gone through a round of layoffs and was facing another.

Ever the gambler in business, Barry had lost a drug patent case in the summer of 2017 and Apotex was likely going to have to pay $580 million to a rival company in January 2018. My sources told me Barry had little cash liquidity and was scrambling for ways to pay. The sources said Barry wanted Jonathon and his business partner to help by putting mortgages on their chain of nine self storage properties, all purchased with interest-free loans from Barry.

Jonathon responded to me over email, confirming some of what I had put to him. But he stressed his father was committed to future funding when his financial picture improved.

In short, my father was always very supportive of me and my businesses, including throughout 2017," Jonathon wrote me on Dec. 12, 2020. He did have his moments where he had more available cash for investing, and sometimes less, and we had mature conversations about this. This is what billionaires do with their sons."

Barry Sherman had provided at least $125 million to Jonathon and Paulin over the years in the form of interest-free loans registered on title to their storage company, Green Storage, along with money for homes and a cottage. My own review of public land title documents suggested that more than $200 million was made available by Barry, but Jonathon said that he and Paulin only ever needed $125 million of that amount.

In our interview, Jonathon spoke highly of his relationship with his father, and said everything" he and his business partner did was made possible with money his father loaned them from Sherfam, the family holding company. He said his father was all in with Adam and me" in the storage business.

Leading up to the interview, Jonathon forwarded a series of emails he exchanged with his father in the six months before the killings. He said the chain begins in July because that is when it became clear Apotex might have to pay out the massive judgment.

On July 27, 2017, Barry writes to Jonathon and Paulin: We are presently unsure what are (sic) liquidity situation will be over the next six months so I am reluctant to have (the family holding company) Sherfam advance more to you in the short term." Barry adds that Jonathon and Paulin should consider borrowing from banks.

On July 27, Jonathon replies to Barry, copying Paulin: OK, good to know. Thanks." Jonathon then teases his notoriously grammatically correct father for typing are" instead of our." In our garage interview, Jonathon tells me he always enjoyed poking" his father, teasing him.

On Nov. 16, Barry writes to Jonathon and Paulin, copying Alex Glasenberg, Sherfam's chief financial officer. Subject line: Arranging mortgages. We might have to pay the 580 million judgment in January," Barry writes. We thus need to take steps to improve liquidity, in case needed. I thus request that you discuss with Alex and arrange first mortgages to enable repaying 50-60 million to (Sherfam) if possible. Please do within weeks." Barry adds, I am certain we will be able to advance further substantial funds to you, if wanted for further investments, beginning in 2019."

On Nov. 26, Paulin writes to Barry, copying Jonathon. Subject line: lunch tomorrow. Hi Barry, Hope all is well. Any chance you are free to get a quick lunch with Jon and me? 12 or 12:30 would work." Jonathon, in our interview, said Paulin often suggested they have lunch with Barry, and would send the email. Jonathon and Paulin worked out of free space in the Apotex building, just down the hall from Barry's office.

An hour later, Barry replies to Adam, copying Jonathon. Okay for lunch."

On Nov. 28, the day after the lunch, Paulin writes to Glasenberg, copying Barry and Jonathon. Subject: Short term cash needs. Please see attached a breakdown of our immediate cash needs. Barry has agreed to cover us with these needs." Paulin and Jonathon were requesting $6.2 million by Dec. 15 and another unspecified amount no later than Jan. 15." In my interview with Jonathon, he said they needed this money to fund plans already in the works to build out" some of their storage facilities.

Three minutes later, Barry writes back: Adam: As discussed, you have to take steps immediately to arrange mortgages (to repay the $50-60 million). What will you do and when?"

Paulin replies to Barry, copying Glasenberg and Jonathon: Hi Barry, Yes, we are restarting these conversations with the banks to get this sorted out as soon as possible." Adam says it will take time and money" to get appraisals" and arrange the bank mortgages, particularly as it is the holiday season, adding the requested ($6.2 million) funds should get us through until financing is available."

Barry replies to Paulin, copying to Jonathon and Glasenberg: Ok but please do asap in case needed."

Two days later, Jonathon and his husband, Fred Mercure, flew to Japan for a vacation. Jonathon says he believes Paulin had conversations with two banks regarding the mortgages. While in Japan, he said, he started learning and trading" cryptocurrency and put the whole matter of the mortgages out of his mind. He said there were no more emails about the funding issue. He and Mercure would return home on Dec. 12, in the evening.

I suggested there were gaps" in the email chain he provided, but he said there were none.

The Star has obtained one additional email chain from that fall which reveals an acrimonious exchange between Barry and Jonathon two weeks prior to Barry's first request for the payback. The subject of the email chain is a potential meeting to discuss the challenges of the various family businesses Barry runs, particularly Apotex.

This email highlights one of the sticking points between father and son, friends of the late Barry Sherman say - Jonathon's insistence that Paulin be present at any business discussions, whether about Green Storage, Apotex or Barry's many other business interests.

On Oct. 27, 2017, Barry writes to Jonathon to discuss a meeting about Apotex and his other business interests. I don't want to meet with you and Adam," he says. You are my son." Jonathon responds that he wants to bring Paulin to the meeting, noting that Barry's second in command at Apotex, Jack Kay, will be present. In his email, Jonathon refers to himself as the heir apparent" to the Sherman fortune. Barry replies that yes, you are my son and heir to the empire" but he complains of Jonathon's unwillingness and apparent disinterest" over the years in the Apotex business. Barry adds that Jonathon's hostility persists," but there is no explanation as to what the Apotex founder is referring to. Jonathon writes that if they have the meeting, it will be with Adam present."

Father and son also exchange barbs in their emails over their approach to business. Jonathon writes that everything" he is doing in his own businesses is to build a safe and stable financial base for future generations of Shermans." Barry shoots back that he has been doing that for fifty years with considerable degree of success despite great obstacles."

Jonathon told me the lunch proposed in October never happened, although they did have one in late November with Paulin present to discuss the short-term cash needs of Green Storage, along with Barry's request for the repayment of the $50 million to $60 million. I ask Jonathon why it was so important for him to bring his partner to a family business meeting, given that his father did not seem to like that idea. Jonathon says it may be a confidence" issue with him - he does not like doing things on his own. Two years previous, Jonathon had written an email to his father suggesting that he and Paulin could play a role in succession" relating to the Sherman holdings.

Paulin, who has not responded to interview requests from the Star, has been Jonathon's close friend since they met at Camp Winnebagoe summer camp. Paulin's family founded the H. Paulin & Co hardware company in 1920, a top retailer of hardware to chains like Home Depot. Jonathon says that, like him, Paulin had no interest in his family's business. Paulin is a graduate of the Ivey business school at Western University in London, Ont., and Jonathon - who has an engineering education from Columbia in New York - says he relies on Paulin's financial background to support their business endeavours.

A couple of hours into our interview, there is a knock on the side door of the garage. Jonathon gets up. It is one of his security team doing a health check" to see if Jonathon is OK.

Yup, all good," Jonathon says, returning to his seat. When their parents were killed, the Sherman children hired security guards who had previously worked for Bank Hapoalim in Israel. A detail was assigned to all four children, and as well as Apotex executives including Jack Kay. Kay lost his security detail when Jonathon fired him, a year and a day after Barry and Honey were killed. To this day, the security detail is never more than a few metres from Jonathon, his sister Alex and Alex's husband, Brad, whenever they leave their homes. I do not know if the same applies to siblings Kaelen and Lauren, who have not replied to interview requests.

The log cabin beside the garage, Jonathon explains, was the home he and his husband originally lived in. With two children by surrogacy (Barry funded the process in late 2017, paying $329,286 to a U.S. company on Jonathon and mercure's behalf) the couple needed more room and have moved to a larger house nearby. At Jonathon's request, the Star is not identifying where they live, other than that it is in the GTA.

Our conversation continues. I tell him that no bank mortgages were registered on his storage properties in late November or early December 2017, as his father had requested. Jonathon said they did start conversations with the banks" but due to the deaths of his parents and the eventual division of the multibillion dollar Sherman estate - which was divided equally among the four siblings - the financing was not necessary. The $580 million legal judgment against Apotex was reduced during a negotiation and later paid, Jonathon told me.

As to the $125 million in interest-free loans his father had advanced his company over the years, Jonathon said he paid that money back to the Sherman estate from his first dispersal" of funds from the estate. (The money is being released to the four children in stages, although much of the fortune is tied up in Apotex which remains for sale.) Every dollar borrowed has been returned," he says.

As to the request from his father to repay the $50 million to $60 million, Jonathon tells me that my questions are making a lot more of that request" than he did at the time. We never really saw it as a threat," Jonathon says. He says a shareholder agreement existed between father and son that said we never have to give you back any money."

Through the garage windows, I can see the snow has picked up. We move to a new topic, the deaths of his parents and the sometimes duelling police and private investigations.

It was just before noon on Dec. 15, 2017, Jonathon says, as he and Mercure were pulling into the driveway of the new cottage on Chandos Lake when his aunt, Mary Shechtman, called from Florida. She had just heard from Elise Stern, the Shermans' realtor, who had discovered Barry and Honey's bodies in the basement pool room of their home on Old Colony Road. Your parents have been murdered,'" he says Shectman told him, adding that she was slightly hysterical." Jonathon says he called his older sister Lauren, who was vacationing in Mexico, before he and Mercure drove back to Toronto, where the family gathered at sister Alex's house in Forest Hill.

Within hours, the family heard rumours that police were considering the deaths a double suicide or a murder-suicide, a fact born out by search warrant documents unsealed by a Toronto judge.

Jonathon says it was he who pushed for a private investigation team to get an independent pathologist to do a second set of autopsies. (The four Sherman estate trustees, including Jonathon, had retained criminal lawyer Brian Greenspan to co-ordinate a private probe.) Jonathon says his only hope was to show that their parents did not have a terminal illness, which might have explained the early police theory. He was pleased when the private pathologist proved" it was a double homicide. When the Star published the results of the second autopsies in January, Toronto detectives interviewed the family's pathologist, and announced it was a targeted" double murder a few days later.

He credits himself for the achievements of the private investigation, saying that without his input, this would have been wrapped up and done with as a suicide."

While he, his sister Alex and her husband Brad were allied at the start of the private probe - having regular meetings together with Greenspan and private detective Tom Klatt - Jonathon says that at some point, Alex started thinking he was somehow involved in the murders. Eventually, she hired criminal lawyer John Rosen to push Greenspan to end his probe and give everything it had collected to the police. That happened in late 2019 and Toronto police say they are still going over 20 gigabytes of information compiled by the private investigators.

Jonathon says he and Alex, who are just three years apart in age, were always close growing up and he is upset that they no longer speak. He says one of his siblings has told him that Alex thinks he carries a gun at all times and is going to pull it out" and shoot her in front of everybody."

(The Star has revealed that there is a major rift between Jonathon and his three sisters, in part over a dispute between Jonathon and Alex over how Sherman charitable dollars are spent).

Jonathon says claims that he would hurt anyone are unfounded and he always treats people with respect."

As to his own relationship with his mother and father, he says it was generally good. Jonathon says that had he been a straight boy," the his relationship with his mother would have been perfect. His being gay was something that upset Honey in earlier days, he says, but she and Barry made his husband feel welcome." He says Barry, whose best friend and first business partner from the 1960s is gay, was more accepting, but once told him that his would be a harder life." The last email Jonathon says he sent his father - on Dec. 14, 2017, when police believe Barry and Honey were already dead - was to invite him to a Christmas party at his forested compound with Mercure and Mercure's family.

With the Greenspan probe shelved by late 2019, Jonathon says he launched his own private investigation led by Robert Seiden a lawyer and former prosecutor from the Manhattan District Attorney's Office who now runs the U.S.-based company called Confidential Global Investigations. He says he hired Seiden because of Seiden's personal history - he pursued a law career after his brother, an innocent bystander, was killed during a mob hit.

As part of his investigation team, Seiden has hired a former Toronto police homicide detective who has good" relations with the Toronto force, Jonathon told me.

When Jonathon gets information, he says, he passes it on to the police. Recently, the lead detective on the Sherman case, Det. Sgt. Brandon Price, visited Jonathon to personally receive a package of information he said he has uncovered.

Our conversation bounces back and forth. It is now dark outside. We are moving through many of the questions that I have asked him by letter and email over the years. Jonathon explains that he always wanted to respond, but felt that it was not the right time until now.

I ask about his emailed suggestion to his sisters in 2015 that their father was incompetent. According to my sources, as well as emails I obtained, this was because Jonathon was concerned that Barry was wasting millions of dollars on his friend Frank D'Angelo, a Toronto juice magnate and filmmaker whom Barry had bankrolled for years.

Jonathon says telling his sisters their father was incompetent was just a figure of speech," and that Barry had brushed off" the suggestion. Life went on, he says, because his father knew he was never going to try and have him declared incompetent." As with other teasing he had done, Jonathon said he was just trying to poke him" over the D'Angelo funding from time to time.

The day before he made that suggestion to his sisters, Jonathon sent an email to Barry seeking $150 million to purchase one quarter of the cottages on Chandos Lake, plus an additional $100 million to expand Green Storage. Jonathon says this was not a real request for money, but rather another poke" at his father for his continued funding of D'Angelo, suggesting the money would be better spent on him.

I put it to Jonathon that various Sherman family members are no longer speaking with each other, and ask about Mary Shechtman, Honey's sister and best friend, who was ostracized by the four siblings soon after the killings when she claimed that Honey had promised her $300 million. Barry had given Shechtman a storage locker at Green Storage free of charge. Jonathon acknowledges that his management team had questioned the free space and evicted her - Jonathon was present last fall on the day that she moved out of the unit in Ajax. I suggest that was harsh and Jonathon replies that there has been a lot of hardship lately."

I also ask Jonathon about his whereabouts the week of his parents' deaths, particularly the Wednesday evening. In our email exchange in December, Jonathon had shared a photo he took of his hand and a note with the time code of 7:17 p.m. Wednesday, December 13, 2017, and the location of his home visible on the smartphone photo. Police have said the Shermans were killed that evening, likely between 9 p.m. and midnight.

Jonathon says he snapped the photo that evening to have a record of a seed code" for his cryptocurrency account and that the hand in the photo is his. He says he also has a photo on his phone taken the next morning at 8:30 a.m., and the location is at his home.

I suggest to him that a photo of his hand taken at 7:17 p.m. at his family compound outside Toronto does not necessarily mean he could not have gone to his parents' house later that night. Jonathon agrees, but says he has always assumed that whoever killed his parents hired someone else."

In the police search warrant documents recently made public, Jonathon is quoted by a detective saying during his interview soon after the killings that there were people who had a grudge" against his parents and a reason to hurt them." Who those people are is blacked out by a judge's order. He says he has given his thoughts on his suspicions to detectives.

On the issue of suspicions in general, Jonathon acknowledges that not answering certain questions posed by the Star over the years, and the issue of the repayment request from his father might be seen as suspicious." But he says, with a billionaire" you will always find things that are suspicious."

I don't know anyone who can plan a murder in three weeks, but I can tell you I was not involved," Jonathon says.

He says Detective Sgt. Brandon Price, who leads the homicide probe, is very professional" and when they spoke recently Price did not reveal what direction police were focusing their efforts on. I tell Jonathon that one of Price's detectives told a court hearing that the estate of Barry and Honey Sherman - who receives and does not receive money in accordance with Barry's will - is embedded" in the police investigation. I ask if that is an indication that detectives at some point looked to see if family was involved. I would hope they have looked at all the family," Jonathon tells me.

He says that he does not put much stock" in what people think about him. I only ever do what I think is right." I point out how very Barry Sherman that is of you."

You could argue that," he replies.

Later that evening, when I am home, I send Jonathon an email thanking him for meeting with me. He replies:

Ok. I just updated (Det. Sgt. Brandon) Price on our conversation." When I tell him I am surprised he did that, he writes back, I kept the police informed because I maintain transparency with them."

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