Winter dove into the lasagna. He’s fifty-five years old, with dark wavy hair swept back off his forehead. He ate quickly, encouraging me to do the same. Winter speaks with a buttery smooth voice, and he talks in run-on sentences. In another world, I could imagine him being a late-night talk radio host, always with one more story to tell in a stream of chat that, on this day, flows from Sherman to drugs to his days growing up and back to Sherman.
Having heard the news of the bodies being discovered, Winter said it brought to mind his long-standing fear that his brother Jeffrey might one day “go off the deep end” and kill Sherman. Jeffrey had struggled with mental health issues since he was a teenager and can be difficult to manage. In fact, Winter said, he mentioned his concern about Jeffrey to someone just two days before he heard about the deaths. With all that rumbling around in Winter’s head, he began panicked attempts to reach Jeffrey, who lives a reclusive life in Mississauga, just west of Toronto. When he heard radio reports that police were at a home in Forest Hill, near where their adoptive parents, the Barkins, lived, he feared that police were there to arrest his brother. Unlike Winter, Jeffrey Barkin had remained in touch with his adoptive parents. (Police were actually in Forest Hill to meet with the Shermans’ adult children at the home of daughter Alex Sherman.)
Winter said he kept calling. Finally, Jeffrey picked up the phone at his home.
“Jeffrey, Jeffrey, are you okay?” Winter said he asked.
“Yes,” Barkin responded, “why?”
“Where have you been?”
“Well, I’ve been about,” Barkin replied. “What’s going on?” When Winter mimicked his brother’s response, he did it with a slow, deep drawl.
“Have you heard the news about Barry and Honey?”
“Yes.”
“Did you do it?”
“Hell, no. I can’t believe you would think I’d do something like that.”
Winter said he hung up the phone, and a few minutes later his girlfriend called.
“Kerry,” she said. “Tell me the truth. Did you do it?”
“I said no,” Winter told me.
“But Kerry, you always talked about doing it,” his girlfriend said.
* * *
—
The anger between the brothers and their cousin Barry has deep roots that twist and tangle like old trees growing too close together. The roots spread out into a series of family and business decisions that reach back fifty years into the 1960s. The four sons of Lou and Beverley Winter are, from oldest to youngest, Tim, Jeffrey, Kerry, and Dana. Tim had been adopted when the Winters believed they were unable to have children. Then, soon after baby Tim was brought home, Beverley became pregnant. Three boys were born, one each year, beginning in 1960. Their father, Lou, was the younger brother of Barry Sherman’s mother. A university-educated chemist, Lou founded Empire Laboratories in the late 1950s and hired young Barry to do odd jobs when he was in high school. When Lou died suddenly of an aneurysm and seventeen days later Beverley passed away after a lengthy battle with cancer, the four boys were left without parents.
According to an account in Toronto Life magazine in 2008, Beverley, who had converted to Judaism when she married Lou, had stipulated that her own family could not take in the boys. She wanted her children raised as Jews. Kerry Winter says that his mother, on her deathbed, called in the trustees dealing with the family business and “added a codicil to her will where she clearly stated she did not want any family members from her side or my father’s side coming forward to adopt me and my three brothers.” Beverley’s brother Wayne Rockcliffe told Toronto Life that he and his wife would have been happy to raise the boys, but he believes his sister did not want “us to have what was hers,” a reference either to the actual children or to the inheritance that would come from her late husband’s generic drug business. Beverley’s rabbi found a local Jewish family, the Barkins, who legally adopted the four boys and were given access to funds from the business operations and the eventual sale of Empire to Sherman and Joel Ulster. Dr. Martin Barkin was a well-known Toronto urologist who would go on to become deputy minister of health in the Ontario government and president of Sunnybrook Health Sciences Centre. His wife, Carol, was a schoolteacher.
Rockcliffe, who had a successful career as a chartered accountant, tried to help the Winter boys from afar. He made the calls to get his nephew Kerry into a prestigious boys’ school after he had spent time in a juvenile facility in west-end Toronto on drug charges. “I got thrown out of the house at fifteen and landed in jail at sixteen on trafficking charges. I was selling drugs at the time,” Kerry Winter recalls. Meanwhile, there was little connection between Barry Sherman and the four boys as they grew. In answers provided during an examination for discovery as part of the litigation between them years later, Sherman stated that he did visit them when he could, but that he stopped because he sensed from the Barkins that they thought he was interfering in the boys’ upbringing. Sherman was twenty years old when the Winter (now Barkin) boys were toddlers and was just finishing university in the United States when his uncle died. This was the period when Sherman would make his first foray into the generic world with his purchase, in partnership with Joel Ulster, of his uncle Lou’s company, Empire Laboratories. Sherman and Ulster sold Empire to an American firm several years later and Sherman founded Apotex. These points on the timeline—purchasing Empire and selling Empire—would eventually be critical in the two lawsuits launched by the cousins.
As the four boys were growing up, the relationship between them and their adoptive parents was fraught with tension. A split developed that many years later would be displayed publicly in Martin Barkin’s obituary. He is described as the “loving father” of Tim and Jeffrey, and Kerry and Dana are not mentioned. From a young age, Dana and Kerry would revert to using the name Winter to demonstrate their displeasure with the sometimes caustic attitude of their prominent father. In an interview, Kerry Winter has said that he and Dana were subjected to corporal punishment—spanking and a belt—by Barkin. “Dana and I were regularly beaten, a lot of physical abuse,” Kerry says. “Emotional and physical abuse to the point that I am still seeing a psychiatrist and I am 57.” There is no independent confirmation of this, and, as noted, Martin Barkin has since passed away. In an interview by text message, Jeffrey Barkin acknowledged that he and Kerry had very different relationships with their father but would not go into details. When Dana and Kerry moved out, Jeffrey and Tim stuck with the Barkins. Though Dana and Kerry, with their early struggles with addiction, could not have been easy children to manage, there are many accounts from people who were Barkin’s colleagues that describe him as having a difficult temperament. Barkin, who had a key role in developing Ontario’s health policy in the 1980s and beyond, was well known for his belief that his way was the only way. As one senior official in the Ontario Medical Association, which represents doctors, put it, “The biggest knock against Martin that I am aware of is that he really does not want to listen to anybody else.”
Kerry and Dana fell out of touch with their adoptive parents after they moved out, and life settled down at the Barkins’ Forest Hill home. Tim (his first name is Paul, but he goes by his middle name), the eldest, who was adopted twice, first by the Winters, then the Barkins, developed an interest in cooking and worked towards being a chef. He is an outlier among the four, seemingly not affected by any demons. Jeffrey had “mental health issues” and “emotional problems,” according to statements in the court case between the cousins and Barry Sherman. Those statements were made, respectively, by Kerry Winter and Barry Sherman. At one point, his sister-in-law Julia (Dana’s wife) filed an affidavit saying Jeffrey was “under disability” during the case. Kerry openly says his brother Jeffrey was “bipolar” and struggled in early adulthood, but maintained a good relationship with his parents. (Jeffrey told me he preferred not to answer questions about his past.)
By various accounts
in court papers, and as stated by Kerry in interviews, none of the four young men had contact with Barry or Honey Sherman until a mutual acquaintance brought Dana and Barry together in the late 1980s. Sherman had learned from the friend that Dana was mired in a cycle of drug addiction and stints in treatment centres and agreed to meet his cousin at Apotex. Sherman’s belief was that a good job and hard work could cure all ills. He hired Dana to work in the production plant, but within a month he heard that Dana was dealing drugs to other workers at Apotex. Sherman’s next plan involved Dana working outdoors at his latest venture: Deerhurst Resort, in Ontario’s cottage country.
Sherman had purchased the Muskoka resort in anticipation of the Ontario government awarding its second casino licence. There was already a flourishing casino in Windsor, across the US border from Detroit, and the well-connected Sherman had picked up the political rumour that Ontario was considering awarding a second licence to a First Nations group that would have ties to a municipality north of Toronto. He set about renovating the tired resort and building a world-class eighteen-hole golf course on the property, and began looking for a First Nations group that would lend its name to the project.
Fred Steiner recalls going up to Deerhurst as Sherman’s guest and asking Sherman what he thought about his new course, completed the year before. “Haven’t seen it,” Sherman said.
Steiner insisted on taking a golf cart and a club and dragging Sherman out to one of the shorter holes to see if Steiner could launch a ball perfectly onto the green. Along the way they passed Dana Winter, who was chatting with some of the female guests. Women who knew Dana, including Sherman friend Bryna Steiner, describe him as having “movie-star looks.” He had blond hair, sharp, almost perfect features, and was a charmer. Within a year, Dana was dismissed from the resort because the handsome and charismatic man was sleeping with the female guests and, according to Sherman in an allegation he made at a court proceeding, dealing drugs again.
By the early 1990s, the pattern was set. The three young men, Jeffrey, Kerry, and Dana, would come to Sherman with their plans and he would bankroll them. Tim never did. It is unclear exactly how much the three cousins received from Sherman, but a conservative estimate, based on court records from what would become protracted litigation, suggests that Sherman gave them a total of $15 million. That money went to fund business ventures: Kerry in construction; Jeffrey in several businesses, including sport travel booking and custom music CDs; and Dana in retailing items of jewellery. Court and property records show that Sherman funded their purchases of homes, cottages, and cars. Honey Sherman was not pleased with this and objected to her husband giving money to the cousins, but Sherman said he had an obligation to help his late mother’s family.
In answers he provided under oath as part of the cousins’ lawsuit the year before Sherman died, with Kerry Winter in the room, Sherman was asked by the cousins’ lawyer, Brad Teplitsky, if over the years he was interested in protecting his cousins’ interests. Sherman replied, “To some extent, I’m interested in protecting the interests of all human beings.”
Asked for his theory on why Dana, Kerry, and Jeffrey were troubled, Sherman appeared to blame them, and possibly their parents and the Barkins, for their ways. “The proof’s in the pudding,” Sherman said twice during the proceeding, but he did not elaborate other than to say that when he became involved again in their lives in the late 1980s the “boys were in trouble.” Drugs, for Dana and Kerry, were the big problem; both were heavily addicted to cocaine and heroin. Jeffrey was not a drug addict, but he was under treatment for mental health issues for many years. At separate points in the protracted litigation between Sherman and his middle-aged cousins, both Jeffrey and Kerry were the subject of motions in court to have litigation guardians appointed because there was a concern that they were unfit to represent themselves. Ultimately, they both continued to represent themselves.
By the early 1990s, Dana’s life had begun to blow up in a spectacular manner. With Sherman’s support after he lost his job at Deerhurst, Dana moved to western Canada to attend a drug rehabilitation program. Out of rehab, he met Julia Zwicker in a small town in Northern British Columbia. They married and had two children. During that time, Dana stepped back into the underworld and got more deeply involved than he had been in Ontario. The man with the movie-star good looks became embroiled in a case that would leave one man dead and Dana and another man facing murder charges over a targeted killing. In 1994, the body of Landis Heal was found in the woods in Northern BC, shot once through the head with a 45-calibre handgun. Police believed that a man named Tim McCreery killed Heal to settle a drug debt McCreery had with Dana Winter. Winter, police alleged, wanted Heal killed for “ratting” him out to the police over an earlier drug deal. Detectives used what, in police vernacular, is called the Mr. Big ruse and pretended they were fellow drug dealers who wanted to get into business with McCreery. In time, McCreery opened up about the killing to his new “friends,” men who were actually undercover detectives. Then McCreery implicated Dana Winter. To assist his cousin, Sherman flew out to BC to hire a criminal defence attorney and put up the $100,000 bond to get his cousin out on bail. Dana thanked Sherman and then disappeared onto the streets of Vancouver.
Dana “was dead a couple of weeks later from an overdose,” Sherman recalled in his examination for discovery. The trigger man on the case, McCreery, was sentenced to life in prison.
* * *
—
Now there were three cousins: Tim, Kerry, and Jeffrey. Tim continued his work as a young chef in Toronto. Jeffrey, while at university, had begun to take a strong interest in his own roots and what happened to the generic drug business Lou Winter had founded many years before. Just exactly what had happened to Empire Laboratories? Jeffrey wondered. Was it possible he and his siblings had some pot of gold that was just lying there for the taking? He and his brothers were aware that Royal Trust had been appointed the estate trustee and that Barry Sherman had purchased Empire, but little else was known. Jeffrey’s private investigations would end up playing a pivotal role in what was to dominate all of their lives for the next two decades. But it was Kerry who was struggling the most. A drug habit that had begun in high school intensified when he became an adult. Cocaine and heroin were his drugs of choice. Kerry says he got hooked on those drugs while backpacking through Peru following a failed attempt to complete a master’s at San Diego State University. Kerry had received an undergraduate degree in London, England at Richmond College and said he was able to manage his addiction during that four-year stretch. But it was when he started travelling in South America and Asia that he began using heavily. “I was a full-blown crack-head. I started using coke in Peru. I put a form called ‘paste’ in a cigarette and smoked it.”
Back in Canada, Kerry Winter began visiting Sherman at Apotex. People who worked in the office in those days, in the late 1990s and early 2000s, recall that Winter was allowed access to the Apotex inner sanctum. One day they were chatting and Sherman said, “Kerry, do you know why I like when you come up and see me? You are so euphoric. You make me laugh.”
Winter was often on drugs when he visited Sherman, he said, and his cousin seemed well aware of that and would accuse Winter of being high. As he had done with Dana, Sherman gave Kerry a job. Winter recalled Sherman handing him a pair of boots and telling him he could work in the stockroom, and if he was not clean of drugs in ninety days, Sherman would pay for him to enter a drug rehab program. Winter had reservations about rehab. He had seen Dana go through two Sherman-funded one-month rehab stints, each costing $20,000, and to him it seemed like a “revolving door.” He took the boots and worked as an order picker in the Apotex logistics warehouse, driving up and down the giant shelves filling orders for customers.
“On the ninetieth day, I walked into Barry’s office and dropped the boots on the floor,” Winter said.
Sherman looked up from pages on his desk. “Are you going to treatment?�
��
“No, Barry. I am clean.”
Winter said that Sherman later attended a ceremony at his Cocaine Anonymous group, where Kerry received a medallion celebrating one year of sobriety. Sherman stood up and told the room of addicts how proud he was of his cousin.
“There is a long history where Barry was really good to me,” Winter said.
Back in the diner, a server cleared our plates, and I could see she was taking a little extra time. Recounting his memories of conversations with Sherman, Winter became more and more animated, waving his hands, tapping them on the table. Winter spoke loudly and forcefully as he described his more critical thoughts on his late cousin. He could be heard at nearby tables and had caught the interest of other diners. One man fumbled with his phone, leaning a little closer while pretending not to listen. Winter’s negative comments about Sherman were in complete contrast to the feelings that friends Fred Steiner, Joel Ulster, Jack Kay, Frank D’Angelo, and others repeatedly expressed about him.
“Here are my feelings about Barry. I am not going to call him a serial killer, a sociopath, a pathological liar. That’s for shrinks. I’m not a psychiatrist. I am just a recovering drug addict trying to get through a day. But I can say this: that his idea of friendship, love, honour, loyalty, things that bind people, was a foreign concept. This was a man I don’t think had any friends.”
Winter said that he and Sherman had lengthy chats about life whenever he dropped by Apotex. He said Sherman had a fascination for Winter’s involvement in illicit drugs. Among the questions he recalled being asked by Sherman: “What’s it like to take drugs? What’s that rush like? What’s it like to shoot heroin?”
The Billionaire Murders Page 15