THE BLACKJACK TABLE IN THE CASINO on the Las Vegas strip had an opening. Fred Steiner motioned for Barry Sherman to join him, and they squeezed in between two other gamblers. “Barry, let me show you this game.” Honey and Bryna were off wandering around the strip, and they had all planned to meet up later in the afternoon.
Sherman put down a $10 bet and promptly lost. Steiner, who loved to wager on cards and was just getting started, saw his friend back away from the table.
“Where are you going?”
“That’s it,” Sherman said over his shoulder, walking off. “I gamble every day in business. What do I need this game for?”
To Steiner’s knowledge, his friend never gambled again on that three-day trip to Vegas in 1982, nor did he ever bet on cards again. Sherman saw no point in risking a few dollars for a possible reward in a game of chance. Yet when it came to his business outside the pharmaceutical world, he would happily gamble millions of dollars if he had a hunch he was right. That pattern would continue for his entire life. In an email to his son Jonathon in April 2015 explaining why he chose some investments (money to Frank D’Angelo in particular) and not others, Sherman wrote, “I cannot debate this with you. There are no equations used for an analysis. It is simply a judgment call, implicitly based on intuition as to the expectations.”
Close friends like Steiner, Jack Kay, and Ed Sonshine, and his entire family, were well aware that away from Apotex, Sherman carried on a high-stakes game with a cast of characters strikingly different from the buttoned-down scientists and bureaucrats he spent most of his life with. Many were larger-than-life individuals who, for one reason or another, had trouble finding more traditional backers. And among these characters, no one was more different from Sherman than Frank D’Angelo.
Sherman once described D’Angelo as being similar to a worn version of a famous movie actor. That was on the occasion when one of his in-laws, who did not like D’Angelo, called him at Apotex to say that “Frank D’Angelo is at a store right now buying a hundred-thousand-dollar Breitling watch with your money.” At the time, D’Angelo happened to be sitting on the other side of Sherman’s desk at Apotex. Smiling at D’Angelo, Sherman leaned back in his chair and said to his in-law, “You mean the guy who looks like a bad version of John Travolta? Frank D’Angelo? You don’t have to worry. Frank is in my office and not buying a watch.”
It is difficult for many of Sherman’s friends to fathom what the billionaire scientist saw in D’Angelo. He is a streetwise entrepreneur with Sicilian-Italian roots who purposefully puts on the air of a comic-book gangster but in reality is a singer, songwriter, talk-show host, actor, movie producer, restaurateur, former beer baron, hockey goalie, and apple juice maker, to name a few of his activities. Since he started out in the fruit and vegetable business with his father out of high school, D’Angelo has ridden a financial rollercoaster for his entire life. While he may not have the Midas touch, he has made a great deal of luck over the years simply by working hard and being in the right place at the right time. As a hockey-crazed kid, he was at a game in the Boston Garden when Bruins captain Phil Esposito spotted him outside the dressing room, freezing in the cold of the arena and hoping for an autograph. Esposito, who would later become friends with D’Angelo, took the eleven-year-old into the dressing room to meet Bobby Orr and Derek Sanderson. The movies D’Angelo makes, which Sherman bankrolled and executive produced, all feature different but equally rumpled versions of D’Angelo, who, of course, stars in each movie. He’s the everyman, the tough guy, the guy with the whole world against him who comes through in the end.
D’Angelo was the first person with any real knowledge of key events who agreed to speak to me when I began investigating the deaths of the Shermans. It took a while to believe that he was not inventing his friendship with the late billionaire. D’Angelo told me, and many others, that he loved Sherman like a brother and that the sentiment was returned. However, others, including Joel Ulster, suggest that Sherman treated D’Angelo more like a son. When I met with Jack Kay for the first of two lengthy interviews with him, I asked him if it was true that Sherman and D’Angelo were pals. All true, Kay said. I asked what Sherman saw in D’Angelo. “Frank is a character’s character. What’s not to like?” Kay said. “And Frank is an idea-a-second guy, and he works his ass off. Barry liked people who had ideas but didn’t have the wherewithal to bring those ideas to fruition.”
There were many business outsiders who gained Sherman’s attention over the years, but none with D’Angelo’s charm, which may have been one of the reasons he and Sherman were friends for more than fifteen years. “Frank was very different from the people Barry related to in his business life and his personal life,” Jack Kay told me. While Kay’s practice was to play the devil’s advocate with Sherman, “Frank knew how to stroke Barry the right way…I would tell Barry he was stupid and full of shit. Frank would tell Barry he was fantastic.”
It began in 2001, when D’Angelo’s company, D’Angelo Brands, which produced and packaged apple juice and other products, was unable to get a steady supply of the crushed and filtered apple juice necessary to build market share. It occurred to D’Angelo that maybe he needed his own processing plant. A friend told D’Angelo that a very wealthy man named Dr. Barry Sherman owned a bankrupt plant in Tiverton, a community in Bruce County, Ontario. Due to its proximity to the Bruce Nuclear Generating Station and a special deal provided by the power facility, the processing plant was powered by free electricity. In one of his earlier gambles, Sherman had financially propped up a former friend who had a plan to make juice and beer at the factory. The businessman (who Sherman eventually sued successfully) also had a scheme to make a product that could be fed to cows to reduce bovine belching and flatulence, major contributors to global warming. Those plans had come crashing down, and now Sherman’s money managers were planning to break up the state-of-the-art machinery and sell it off. D’Angelo got an audience with Sherman and his money managers and presented his plan. He would purchase the processing plant for $5 million (which he did not have) and pay Sherman by selling the beer-brewing equipment, which was brand new and had barely been used.
“Let me get this straight,” said Sherman’s brother-in-law, Mike Florence, who was one of his money managers. “You are going to use our money to pay us?”
Florence was visibly angry, D’Angelo recalls, but Sherman raised his hand. “If you can pull it off, why not?”
D’Angelo says Sherman was so impressed, he suggested instead that they be partners. “Go ahead, run with it,” Sherman said, according to D’Angelo.
The processing plant solved D’Angelo’s apple juice problem, and when he took a closer look at the entire production facility he wound up convincing Sherman that they should also become beer barons. The first order of business was travelling to Europe to find the perfect beer recipe, which D’Angelo, a wine drinker, says he did by stopping at the first place he saw on a highway in Belgium. Sherman paid off D’Angelo’s $50,000 credit card bill so that Ontario’s latest beer maker could afford his plane ticket. Out of the Tiverton plant eventually came Steelback beer and some innovative products: plastic beer bottles, lemon-infused beer, and the first “tall boy” cans. Steelback struggled to find a foothold in the competitive Ontario beer market, though it did win gold, silver, and bronze medals in 2007 in several categories at the Ontario Brewing Awards. At the same time, also with Sherman’s financial backing, D’Angelo produced an energy drink called Cheetah Power Surge. He hired as his pitchman disgraced Canadian sprinter Ben Johnson, who in the commercial used the tacky line “I Cheetah all the time.” Friends of Honey Sherman recall her pointing to the canned drink in a store and saying, “That’s one of ours.” One day, D’Angelo had a dozen cases dropped off at Apotex and they sat in the executive hallway for days before they were distributed among staff.
Meanwhile, Sherman and his financial managers at the family holding company noticed that debts were piling up at the brewery and other D’Angelo businesses that Sherman was backing. One problem was that sales revenue was not keeping up with the ever-growing number of events that D’Angelo, with Sherman’s support, was sponsoring around the province. D’Angelo’s hope was that all Ontario Junior Hockey League arenas would one day be Steelback arenas. One hefty sponsorship that racked up the bills was Toronto’s major Grand Prix race car event in July 2007, dubbed the Steelback Grand Prix. During the race, where a big section of Toronto’s lakefront road system is shut down for several days, Sherman was spotted by Toronto businessman Paul Godfrey. Godfrey, a former Toronto politician and well-known financier, who is often at such events, recalled how out of place Sherman was among the grease pits and the noise. “Oh, D’Angelo got me involved,” Sherman explained to Godfrey over the roar of high-octane-powered cars zipping by on the other side of the safety fence.
Later that year, two things happened that would unsettle D’Angelo’s world for a short time. Sherman called him in and told him that he was sorry, but his twenty-five-year-old son, Jonathon, a recent engineering graduate of Columbia University, in New York, was taking over Steelback Brewery after a short stint at Apotex. Not long after, the Shermans put Steelback and some of the other D’Angelo initiatives into creditor protection with a plan to restructure. According to the financial papers filed in court during this time, D’Angelo’s companies were $100 million in debt to Sherman, plus $20 million in interest. While D’Angelo maintains to this day that the restructuring papers paint an unnecessarily bleak picture of his finances, he agreed to take a step back. Sherman provided him with a monthly allowance (D’Angelo will not say how much) to keep him afloat.
“I left there destroyed,” D’Angelo says of this period of his life. “But the man was so good to me, I trusted him, and he looked after me.”
D’Angelo continued to operate the downtown restaurant that Sherman also backed, the Forget About It Supper Club, on King Street, in Toronto’s theatre district. Jonathon restructured the brewery, reducing the number of beer brands drastically, won a few awards himself, and then the company closed up in 2010. With the brewery closed, and Jonathon moving on to other ventures, Sherman gave D’Angelo back control of many of the assets, including his juice plant, and the two men continued as if nothing had happened. Jack Kay watched this all unfold. “I didn’t agree with Barry as to the amount of money he invested with Frank. I said, ‘I don’t think we will see any return.’ But Barry said Frank is one hard-working guy,” Kay tells me.
Today, D’Angelo Brands produces a number of products, including AriZona iced tea and related beverages. At D’Angelo’s annual company Christmas lunch at his Mamma D’s restaurant (with dishes made according to recipes D’Angelo created), adjacent to the soft drink and juice plant he has in Mississauga, Sherman was always seated beside D’Angelo. Sherman would miss the 2017 lunch, held the day before the Wednesday when the Shermans were most likely killed, because he had a scheduled meeting he could not miss.
Just as Paul Godfrey was surprised to learn that generic drug titan Barry Sherman was backing a beer company which in turn was sponsoring a car race, others would be surprised to learn that the seed money behind movies like Sicilian Vampire and The Neighborhood came from the Apotex owner. Sherman shared the executive producer role with D’Angelo on all movies, though Sherman’s contribution was mainly financial.
“When Frank came up with a new script, I would come in in the morning and Barry would have put it on my desk,” Kay says, smiling. “I even had the Vampire poster here for a while.” The formula for the movies was simple, and they were all shot at breathless speed in a week. Beginning in 2013, D’Angelo’s company In Your Ear Productions turned out one or two movies a year. Each featured an actor who was no longer Hollywood A-list but was still a draw, among them Daniel Baldwin, who is in most of them along with Michael Pare, Paul Sorvino, the late Robert Loggia, the late Margot Kidder, and James Caan. Hockey legend Phil Esposito has been in two. D’Angelo said Sherman loved the concept of a movie made quickly and on the cheap though with good production values. As someone who turned out products that had expiration dates, Sherman liked that “our movies had no shelf life,” says D’Angelo. In the last few years, the movies (some had theatrical showings but most went straight to DVD) have started to make money through licensing to Fox and Amazon. Sherman also liked the fact that the Canadian government gave him a hefty tax credit because of the movies’ high Canadian content. Sherman’s only constant criticism was the vulgar language in the scripts. D’Angelo says he patiently told his financial patron, “That’s how people on the street talk.” Jonathon Sherman, however, was not a fan. In a 2015 email exchange between father and son, Jonathon expressed dismay that Barry was continuing to fund D’Angelo, and makes the claim (which D’Angelo vigorously disputes) that over the years $250 million had been advanced to D’Angelo with little return. Jonathon writes, “In the past I have been accused of petulance for asking tough questions, and there has been much frustration for both of us. Years ago I did stop asking about Frank because of the strain it caused on our relationship, and left it alone. I am only asking again now because for the past couple of years ‘cash is tight.’ I have been turning down great investment opportunities, and Frank continues to burn cash at the same rate.” Barry responded by defending D’Angelo, pointing out that “major actors in Hollywood take him seriously” and that D’Angelo was producing films with “value in excess of cost.” Barry included a link to a movie trailer for Sicilian Vampire.
If there is any doubt about the closeness between the streetwise D’Angelo and the nerdy Sherman, their camaraderie is on display in many photos. Dinner parties were held to celebrate each new movie release, and in one photo, a smiling Barry is seated across from such notable actors as Robert Loggia and Tony Rosato. The photo was taken at the dinner celebrating the 2013 premiere of Real Gangsters. To the left of Barry is Frank D’Angelo; to Barry’s right is Honey. Though Sherman went to D’Angelo’s events, D’Angelo was rarely invited to Sherman family events due to the bad blood with Jonathon over the brewery business. D’Angelo was not at the Sherman funeral, at the request of the Sherman children, who asked Jack Kay to deliver the message. Kay did, and promised D’Angelo he would go with him to the gravesite later on, which he did.
In the weeks immediately after Barry and Honey died, family openly floated the idea that D’Angelo was either the killer, or that some financial deal he and Barry were involved in led to the attack. D’Angelo scoffs at this idea. “First, Barry was like a brother to me. I loved him. Second, why would I kill the person who has supported me and given so much?” Insiders have told me that since Barry Sherman died, D’Angelo has had his funding cut off. Over the life of my investigation, D’Angelo was one of several people who frequently touched base, often helping me gain access to good friends of Barry Sherman who otherwise would not have spoken to me. He, like the Sherman children, had his own theories and he was never shy to relate them. As I did with many people, I asked D’Angelo where he was on the Wednesday night the Shermans died and on the Friday when the bodies were discovered. At the time, D’Angelo and his partner, Gemma, had between them two houses, one in Stouffville, north of Toronto, and one in Kleinburg, northwest of Toronto. Gemma works in the office with D’Angelo at the Mississauga plant. On the morning of Wednesday, December 13, 2017, D’Angelo said he and Gemma were at the Stouffville house and he left early to play his regular hockey game with friends in Toronto. He left the rink, went to work at his Mississauga plant, and at the end of the day, the couple went home to Stouffville. Gemma, who was pregnant at the time (the couple now has twins) said that Wednesday night she and D’Angelo were at home together watching television. The next day, Thursday, Gemma went to work and D’Angelo worked from home in Stouffville, co-hosting a web-based sports radio show. On the Friday, they drove up to Collingwood, two hours northwest of the city, and Gemma, in the passenger seat, got the news of the Sherman deaths on her phone. Gemma, who had met Barry Sherman many times at the annual Christmas party and at meetings with D’Angelo, said the rumpled billionaire reminds her of another well-known tycoon. “There’s always a social media post of Bill Gates standing in line for a taco. I will see that and say, ‘That’s Barry’. You never knew what he had.” Both D’Angelo and Gemma were interviewed by Toronto homicide detectives and gave the same account they provided me.
There was only one Frank D’Angelo in Sherman’s life, but he backed many others on short-term ventures as diverse as a dating app and a condominium tower. As Jack Kay explains, when one is a billionaire, people will drop by the office with a pitch, a scheme, an idea. Quite often, those people ended up in court being sued by Sherman. And these actions—often involving relatively small sums of money—contributed to the belief that Sherman was overly litigious. “You hit Barry Sherman with a fly swatter, he’s coming after you with a fucking sledgehammer,” D’Angelo says.
Sometimes Sherman ended up on top; sometimes he lost millions. But he always kept fighting. “Barry’s not a quitter,” says D’Angelo. “Barry’s not a type of guy who would swim halfway across Lake Ontario, get tired, and swim back. He’s going to fucking make it all the way.”
Sherman’s ventures were run out of his family holding company, Sherfam Inc., incorporated in 1991. Headquartered a kilometre from Apotex, on the second floor of an ugly three-storey brown-brick building populated by insurance companies and law firms, Sherfam did not look like a multi-billion-dollar enterprise. While Sherfam’s accounting functions were run out of the building, under the watchful eye of South African–born Alex Glasenberg, the Sherfam chief financial officer, Sherman rarely set foot in it. Those who wanted an audience visited him at Apotex.
Pitchmen typically got in to see Sherman because of some previous connection, through social circles, a chance meeting, or, quite often, Toronto’s Jewish community. The person would book an appointment and, on a day when Sherman had a few spare minutes, find themselves sitting across the cluttered desk from the billionaire. That’s the way it had been with D’Angelo years before. By all accounts, Sherman had a remarkably short attention span unless something interested him. It was not unusual for him simply to get up and walk away during a conversation if he was bored. Kay says that when someone showed up with a “good story” but not one Sherman was captivated by, the easiest way to get the man out of his office was “to write him a cheque.”
“Or, if there was more substance, Barry would say, ‘Go see Jack,’ and I would take it from there,” Kay says. Though second in command at Apotex, Kay was often called upon by Sherman to assist with his Sherfam investment plans. Kay and Glasenberg were typically not in agreement with these pitches for get-rich-quick schemes. Sherman was already wealthy, so why take on the headache of a scheme that did not look good on paper? Over the years, Kay would sometimes get very upset with Sherman. He would go home and discuss it with his wife (he remarried after he joined Apotex), suggesting to her that if this kept up he would have to leave Apotex.
“My wife and I had the discussion, and [at dinner with the Shermans] my wife would say, ‘Barry, you are going to force Jack to resign,’ ” Kay recalls. He never did, of course. “Once Barry made the decision, whether I agreed or not, he was the owner and the decision-maker. My job was to operationalize it, whether I agreed or not.”
In 1985, ten years after Sherman started Apotex, an investment scheme involving high-end yachts caught his interest. He was a long way from being a billionaire then, but he had made a few million dollars and he hated paying taxes (which his Conservative friends found odd, since Sherman was a lifelong Liberal, a party historically known for funding big government initiatives through increasingly higher taxes). Sherman was always on the lookout for a way to avoid paying taxes. In later years, he had his accountants create a labyrinth of companies, registered in Panama and other tax haven jurisdictions, to shield Apotex profits. But in the 1980s, he was attracted to ready-made schemes, and that led him to the yachts. Einar Bellfield, a Norwegian man a judge would years later describe as suave and intelligent, set up a tax shelter that promised to reduce taxes payable for wealthy businessmen. Bellfield used tax accountants and lawyers to peddle the concept, and one of them made a successful pitch to Sherman. Fantaseas, also known as Overseas Credit and Guarantee Corp. (OCGC), was raising money to build a fleet of luxury catamarans to sail the Mediterranean and Caribbean. The plan was to build or purchase a fleet of seventy-five boats and lease them to short- and long-term customers. Investors were “loaned” money by OCGC to buy into the scheme and were to make monthly interest payments on the loan. The interest payments and any losses the investors incurred could be deducted from their annual income tax payments to the Canadian government.
In addition to Sherman, more than six hundred others eventually invested in the tax scheme, including Michael Bregman, founder of Marvellous Mmmuffins and the man who purchased and took Canadian coffee chain Second Cup public. This big group of investors, many from the highest echelons of the Canadian business elite, were lured in by lawyers and accountants who received hefty commissions for securing seed money. Some of the glitzy Fantaseas promotional events were held at Toronto’s Casa Loma, a Gothic revival style mansion located in midtown. Working out of the den of his condominium, Bellfield, his wife, and a partner created an impressive series of brochures that depicted the fleet of yachts, complete with gleaming state rooms and with glamorous names like The Great Gatsby, Elegance, Garbo, Gable, and Casablanca. Each year for the next five years, Bellfield and his small team would send out detailed statements to investors describing the growing fleet, with some boats purchased and the majority being built from scratch in shipyards around the world. So specific were the documents that they described the purchase of plush interior supplies right down to linen tablecloths. As to paid charters, many had already been booked, the investors were told.
What no one realized, or apparently did not turn up through the due diligence one would expect of shrewd investors, was that Bellfield was a charming fraud. He had just been discharged from bankruptcy in Canada and was facing fraud charges over some other schemes, and the entire corporate web that attracted Sherman and others was a sham. Only two yachts were ever acquired, and each was sold almost immediately. Fantaseas was a complete fabrication, as investigators and a criminal court eventually found. Bellfield was sentenced to a decade in prison and ordered to pay a $1-million fine, punishments that were unusually harsh compared to other white-collar prosecutions in Canada. In the case files, federal investigators detail how the scheme deprived the Canadian government of several million dollars of tax revenue and deprived investors of much more.
The real pain for investors, including Sherman, came when Canadian tax authorities reassessed years of tax returns and found that the losses the investors had been claiming to reduce their payable income tax were, like the yachts, a mirage. Since there were no yachts, there could be no losses. One of Bellfield’s pitches was that since seagoing yachts depreciate quickly in value, the investors would be able to record the depreciation as a loss. No boats, no depreciation, said the taxmen—and they were right.
Caught with their financial pants down, most of the six hundred plus investors made a deal with the Canadian tax authorities and settled. Not Sherman. He kept fighting for several years, though he too eventually cut a deal. He agreed that his deductions should be disallowed, and as part of the settlement agreement the amount he owed was reduced. But Sherman sued Orenstein and Partners, the accountants Bellfield used to prepare financial statements for his scheme. Sherman claimed that the accountants were negligent in not providing a warning in their reviews that Bellfield’s company was not a “going concern.” Sherman felt that the accountants should have suspected a scam and wanted Orenstein to reimburse him for the $634,996 he had paid in interest during the four years of the swindle. Sherman lost in the lower court, however, and lost again at the Ontario Court of Appeal.
It is quite likely that to do battle with Revenue Canada for several years, and with Orenstein and Partners for more than a decade, Sherman incurred legal expenses greater than the amount he was seeking. In his ruling, writing for a unanimous decision of three appeal court judges, Justice John Laskin wrote that the judge whose ruling they upheld had made a keen observation about the Apotex founder after seeing him testify for two days on the witness stand: “[Justice Maurice Cullity] was left with the impression of a man with too many businesses and other responsibilities and interests to pay much attention to his investments once he had made them.”
That Barry Sherman rubbed shoulders with a fraudster was not at all unusual. Around the same time as the yacht scheme, Sherman provided investment funds to Harvey Rubenstein, a shady Toronto stockbroker who would later be convicted of fraud in Canada and the United States. Jailed in Oregon and awaiting trial, Rubenstein telephoned Sherman in Toronto and persuaded the man he had already duped out of more than one million dollars to advance him $100,000 bail money. As Sherman said in a deposition as part of his attempt to recoup some of the money Rubenstein owed him, he saw no point in having the man “languish” in jail. Sherman eventually sued Rubenstein in an unsuccessful attempt to get the bail money back.
Fred Steiner says he was completely unaware of all these private side deals in which his friend was involved. “He never discussed them,” says Steiner. “As good and as close a friend as I am, I can’t tell you about his outside deals.” In retrospect, Steiner, who with Sherman’s help built a very stable coffee service business, says he thinks his friend resisted sharing information about his more unusual deals because he was worried that he would meet with disapproval. “I think he felt that I was so legit, he did not want to burden me with anything that was off the wall. I think he did not want to involve me with anything that I might object to. I also think he did not want to be questioned or criticized. And I would have criticized him.”
Steiner did become aware of one of Sherman’s private deals. Several months before the Shermans’ deaths, a mutual acquaintance told Steiner that Barry had made a substantial investment in the development of The One, a retail and condominium tower at 1 Bloor Street West in Toronto, on the southwest corner of Yonge and Bloor Streets, arguably the city’s most high-profile intersection. Every city seems to have at least one of these troublesome sites: a choice location for all sorts of reasons, but one where developers struggle to get financed and the project built. Developer Sam Mizrahi had been trying to construct a colossal project for several years but had trouble securing financial backers. In mid-2017, a real estate investment trust that was backing the property had withdrawn financing, and Sherman and other lenders, including an Ontario paving company and a firm based in China, agreed to help out. In late August, Sherman advanced $61 million to Mizrahi in a mortgage at the high rate of 13 percent interest. Other investors, apparently assembled with the help of Sherman, provided hundreds of millions of dollars more, and construction on the eighty-five-floor skyscraper, destined to become the tallest structure in Canada, broke ground. Associates of Sherman told me that the interest rate on his contribution was really only 8 percent, not the 13 percent recorded on the mortgage documents. They said Sherman, to help Mizrahi out, signed documents stating that if the deal went smoothly, he would make adjustments in the money owed so that Mizrahi paid the lower interest rate. For reasons that remain mysterious, Sherman told friends he wanted the public to know he was charging a high rate, yet in fact he was taking much less. No matter the rate, why did Sherman bail out Mizrahi?
“Barry did not want Sam to lose the project,” Jack Kay explains.
Born in Iran to Jewish parents, Mizrahi is yet another colourful character in Sherman’s life. Mizrahi’s previous business was a luxury Toronto dry cleaner named Dove Cleaners, which Mizrahi exited around the time it was having financial difficulties and restructuring. He then got into the real estate development business. In recent years, Mizrahi claimed in a lawsuit that some fellow Iranian businessmen in Toronto had threatened to kill him. As a result, Mizrahi told reporters in Toronto that he had gone into hiding for a time. I interviewed those Iranian businessmen, and they said Mizrahi’s claims were “ridiculous.” Both sides are locked in a multi-million-dollar dispute over a series of development properties near the 1 Bloor West development. (Mizrahi declined three requests to speak to me about his business association with Barry Sherman and his friendship with both Shermans.)
Sherman continued to deal with the aftermath of investments gone wrong until the day he died. On Wednesday, December 13, his lawyers filed documents in court requesting an early trial date in a case that involved, of all things, a trivia app for smartphones. Steiner and other friends, when asked about this particular side deal, shook their heads and said Sherman never mentioned that one either. The trivia app deal started the way most of them did. Somebody Sherman knew needed assistance. An old friend, Myron Gottlieb, had approached Sherman in 2015 looking for help. Gottlieb, along with Toronto theatre impresario Garth Drabinsky, had been convicted of two counts of fraud for their role in a scheme to falsify financial statements at their production company, Livent Inc., the firm behind the Toronto production of The Phantom of the Opera and so many other big hits. Investors lost an estimated $500 million when Livent went under. Gottlieb was sentenced to four years in prison for his role and released on day parole in 2013 after serving eleven months. While in prison at Ontario’s “country club” Beaver Creek Institution (located in cottage country and the usual destination for non-violent white-collar offenders), Gottlieb became friends with convicted fraudster Shaun Rootenberg, a flamboyant and fast-talking con man. Once out of jail, Rootenberg began developing Trivia for Good, a smart phone app. Promotional materials for the company stated that the app would generate revenue by pushing advertisements to the user. Rootenberg needed investors, so he first enlisted Gottlieb, who in 2015 turned to Sherman. The Apotex billionaire agreed to provide $150,000 in return for a share in the trivia company, and he instructed his financial people at Sherfam where to send the money.
Documents Sherman later filed in court as part of a lawsuit allege that his investment was diverted to a separate bank account controlled by Rootenberg and others. There never was a fully functioning app. Sherman said he was the victim of a scam, and he wanted his money back. Had any due diligence been conducted by Sherman and his financial people, they would have uncovered Rootenberg’s background and that of others involved in the scheme. As to Gottlieb, Sherman did not go after his old friend. During the same time period, Rootenberg was accused by Toronto Police of “romance fraud,” meeting women on the dating site eharmony and convincing them to invest money with him. (At time of writing, those charges were before the court, as was Sherman’s lawsuit against Rootenberg and other parties.)
Gottlieb declined a request to be interviewed for this book, instead providing a short statement: “My wife and I were privileged to be friends of Barry and Honey. They were an exceptional couple and their death was both a tragedy and was untimely. Others knew them better and for a longer period of time.”
Sherman may not have liked the concept of betting on cards, but he was a risk-taker and a gambler. One of his lawyers told me, “Barry’s risk profile was off the charts.” Jack Kay says this simply about his friend, “Barry was a schemer.” Back in the early 1970s, Joel Ulster had decided to part company with Sherman professionally because he was not comfortable with the risks his friend took. Ulster, Steiner, Kay, and others who knew Sherman very well say they believe Sherman entered into all of these dubious ventures because he believed he was right when he backed someone. In the pharmaceutical world, that was why he backed the researchers on the thalassemia drug. When it came to his many side deals, he believed he had the ability to determine if something was a good bet. As so many of the deals showed, he was not always right. The trial judge in the Fantaseas yacht case quite astutely noted that Sherman’s busy life did not allow him the time, nor did he seem to have the inclination, to either dig in and properly vet a new venture or direct one of his staff to do so. As he said in his 2015 email exchange with his son, Sherman did not use “equations for analysis.” For him, his judgment was king.
Friends say Sherman was a contrarian. Fellow philanthropist and businessman Ed Sonshine says that if the world seemed to be against someone, Sherman would back the man. “He loved helping financially guys who other people told him were bad guys,” Sonshine says. Over the years, Sherman would call Sonshine and ask him for advice. In one instance, where Sherman ultimately advanced $30 million to an individual, Sonshine warned him not to do it. Sherman recouped only a fraction of his investment.
“You want to call it vanity, you want to call it ego, you want to call it an unshakeable belief in his own brain?” says Sonshine. “The more everyone told [Sherman], ‘This guy is not going to work out for you,’ the more he would be interested in doing something.”
On one occasion, Sherman lamented to Sonshine, “Ed, if I only stuck to my own business, I would be a lot richer than I am.” Another time, reflecting on some recent losses, he told Sonshine, “If things keep going like this, I will be down to my last billion.”
Is there a clue to the murders somewhere in Barry Sherman’s business deals? “Follow the money” is something that many people with an interest in the Sherman case have said. Jack Kay says it. Frank D’Angelo says it. The quote comes from the Watergate movie All the President’s Men, and it is attributed, incorrectly, to the government source Deep Throat, who never actually said it in real life to reporter Bob Woodward. But the concept—follow financial transactions to solve a case—is a good one. But without the search warrant powers of the police, it is difficult to do. Sherman’s financial history, holdings, and the estate he left behind are kept secret by court order. Further complicating things is that Sherman’s dealings were intensely private and sometimes sealed with a handshake and little or no paperwork.