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The billionaire founder of pharmaceutical giant Apotex and his philanthropist wife were two people with outsized personalities who were polar opposites, according to interviews with friends, court records, Barry's memoirs and public tributes at the couple's memorial

Barry and Honey Sherman are shown in a handout photo from the United Jewish Appeal. Apotex Inc. says it wants to set the record straight about how the pharmaceutical company will be managed following the death of its founder, Barry Sherman, and his wife Honey.

'Yin and yang' is how family described Honey and Barry Sherman. They complemented each other, yet had clashing personalities.

Reserved, socially awkward and a workaholic, Barry was a pugnacious man who never backed away from a courthouse or corporate fight.

As an entrepreneur, he hired private detectives to rummage through his competitor's garbage, then got a court order so he could barge into their head offices and seize their papers. He didn't hesitate to foreclose on the homes of people who owed him money, even relatives.

"Free will is an illusion … Life has no meaning or purpose," he said in his unpublished memoirs.

Honey was outgoing, with a cutting wit and salty tongue. Feted for her philanthropic work, she had the mettle of someone who survived throat cancer and took part in a charity dance contest after undergoing surgeries for her crippling arthritis.

WATCH Honey Sherman practicing for her charity dance contest

The deaths of the Toronto billionaire and his wife a week ago, deemed by police to be suspicious, has bewildered people who knew them, attracted international attention and provoked endless speculation about how the influential couple could end up hanging from a railing by the basement pool of their North York home, with no sign of forced entry.

Friends close to the couple describe signs of discord in the Sherman's marriage, such as public ribbing about Barry's devotion to work, but they viewed it as shtick. Everyone the Globe and Mail spoke with over the past week has been incredulous at the police's initial theory that it could be murder-suicide. There have been no further details from police about the case.

Interviews with friends, court records, Barry's memoirs and public tributes at the couple's memorial Thursday paint a portrait of two people with outsized personalities who were polar opposites.

Back in 1970, Honey Reich was volunteering at Mount Sinai Hospital when she told a nurse that she was looking for a nice Jewish doctor. That nurse was married to Joel Ulster, a friend and business partner of Barry, a budding pharmaceutical magnate. He was not a medical doctor, but he did have a PhD. The two were introduced.

Barry, the son of a zipper manufacturer, described himself in his memoirs as a lethargic child with a gift for math and science. He lost his father when he was 10 but did not recall a great sense of turmoil. His detached, rational side was also evident while he was in the military reserves, where he would argue aggressively with a chaplain who preached Christianity.

A Legacy Of Thoughts by Bernard C. Sherman by The Globe and Mail on Scribd

The first time Barry came by Honey's home for a date, her younger sister, Mary, was skeptical. Barry stood in the kitchen with his nose buried in a newspaper, ignoring her. "My sister's going out with this?" she recalled thinking.

Their mother, however, was sold. She knew this was the man that Honey would marry. "This guy showed up and the rules went out the window," Mary told some 6,000 mourners at the memorial service, which was attended by Prime Minister Justin Trudeau, Ontario Premier Kathleen Wynne and Toronto Mayor John Tory.

As Honey began to fall for Barry, he grew on Mary, too. He was introverted and undeniably brilliant. (He once told a Globe reporter his IQ was 180 and that he declined an offer to work for NASA. "Maybe I like to be a big fish in a small pond," he said. "Everything comes down to ego.").

The pair married in 1971. It was around the same period that he first ran into legal problems at his generic-drug business, which he attributed to agitation from his competitors.

His company was charged in 1970 with selling drugs that lacked the required potency. He hired a high-profile lawyer, Willard Estey, a future Supreme Court justice, and was acquitted. The following year, a federal board removed Barry's company from a list of approved suppliers. Again, he enlisted Mr. Estey and forced the government to back down.

"This was the first time in my career that I found it necessary to initiate a legal action. It was to be the first of many," he recalled in his memoirs, which are now part of a public legal file.

In court cases, he was unyielding and combative. His judicial disputes embroiled a motley cast of people who crossed his path – relatives, contractors, business rivals.

In a decade-long litigation against Barry for a share of Apotex, the company he founded in 1974, cousins described his actions as "illusory generosity."

In court papers, the cousins alleged that Barry provided them with loans that were secured against their family homes, charged them "substantial interest," then sued them for recovery, "vigorously [prosecuting] those legal proceedings to the point of attempting to dispossess Julia Winter [a widow] and her young children from their family home."

Barry's cousin, Kerry Winter, for example owed him $7.9-million. When Mr. Winter defaulted on the loan, he had to surrender three houses in 2008, which Barry resold in power-of-sale transactions. The same fate befell Toronto businessman Stephen Mernick, who owed Barry $736,000. "At no time did I ever advise Mernick that I would not take possession of the property in the event of his default," Barry said in a court affidavit.

The Apotex facility in Toronto. Barry Sherman founded the pharmaceutical giant in the 1970s.

He was equally hard-nosed with rivals in the pharmaceutical industry. In the early 1990s, as Apotex and its competitor, Novopharm Ltd., raced to manufacture the anti-cholesterol drug Lovastatin, Barry hired private detectives to rummage through Novopharm's garbage, looking for evidence of stolen trade secrets.

He also obtained a civil search order. With the court order in hand, Barry then led his private investigators and a sheriff into Novopharm's headquarters and seized various documents.

There were litigations on other business fronts, for example proceedings stemming from a bad investment Barry made in a tax shelter that purported to charter luxury yachts. The business turned out to be a scam and he had to settle with Revenue Canada. He then sued an accounting firm for failing to flag the problem.

As Apotex became a generic drug giant, the Shermans accrued an estimated net worth of nearly $5-billion. They gifted tens of millions of dollars to charity. They also donated to the federal Liberals, and a 2015 fundraiser they hosted at their home, with Mr. Trudeau as guest of honour, is being investigated by the federal Lobbying Commissioner. Barry and Apotex sued, trying to quash the probe.

At home, the Shermans had four kids; three girls and a boy. The first, Lauren, was born in 1975 – after which Honey suffered several miscarriages, according to a 2008 Toronto Life profile.

"Lauren, you deserve amazing credit for paving the way for me and the girls," Jonathon told his older sister at their parents' memorial service, in remarks that hinted that Barry and Honey weren't always on the same wavelength.

Jonathon Sherman speaks during a memorial service for his parents Barry and Honey Sherman as family members look on in Mississauga, Ont. on Dec. 21, 2017.

"I know it was hard to be an only child when yin and yang were maybe not so balanced, but your free spirit and ability to love life is perhaps your greatest tribute to mom and dad."

Jonathon was born in 1983 by surrogacy, according to the TO Life profile – a time where such a procedure was rare in Canada. At the service, he mentioned that he and his husband, Fred, are now going through the surrogacy process themselves.

A third child, Alex, was born in 1986. The youngest, Kaelen, was born in 1990, the same year the family moved to their custom-built home in North York, on Old Colony Road.

But four years later, the Shermans noticed design and construction flaws with the roof of their underground parking garage and air-conditioning system. Barry and Honey sued those involved in building their house – the design consultants, construction company, architects, engineering firm, landscape architects, landscapers and tennis-court designers.

The lawsuit dragged on throughout the late 1990s. By 2002, the Shermans had settled with mostly everyone except one company. They then sued Ontario's new-home warranty program because it didn't compensate them for the defective construction.

The faulty garage structure at the heart of the dispute, which included a tennis court on top and a sauna and underground pool inside, was a key part of their house. It was used for social events, such as charity functions and formal dinners.

Roz Davidson (left) and Honey Sherman at the Chasing Madoff after party

Linda Waks (left) and Honey Sherman, event co-chair and winner of Dancing With our Stars 2011, at Dancing with our Stars in support of the Baycrest Foundation at the Allstream Centre in Toronto.

Honey was a socialite philanthropist, and loved nothing more than an excuse to celebrate. Holiday get-togethers were one area of their lives where the otherwise frugal couple loved to go all out. What began years ago as a modest family dinner evolved over the years into an 80-person feast, with a banquet table cutting across the entire length of their mansion. In the kitchen, Honey – in her sweatpants and flip flops – would be cooking for everyone.

She was disappointed by her youngest daughter Kaelen's plans to have a destination wedding next May. She wanted to plan a big celebration at home in Toronto, her brother acknowledged at the memorial service.

"[Mom and dad] might not have told you this enough, but I know they were teeming with excitement for your wedding," Jonathon told Kaelen.

When she lost the wedding battle, Honey splurged on an engagement party – which would end up being the family's final get-together.

August, 2006: Barry Sherman is shown with a container of clopidogrel bisulfate, a generic drug for heart disease then newly approved by the U.S. Food and Drug Administration.

Despite their busy household, Barry spent most of his time at the Apotex offices – six days a week, in the company's early years, often working longer than 12-hour shifts. At night, he slept with a pad and pen by his bedside in case he woke with an idea.

Even on vacation, he brought work along. Once, on a family trip to Tanzania in 1996, he got antsy on day eight and decided to start writing a memoir. It contained little mention of his family.

"[This] should not be taken as suggesting that they are not important to my life, as that would be anything but true," he wrote. "However it seems to me that information about my family is likely to be of less interest to a reader than my observations relating to philosophy, Canadian politics, and the pharmaceutical industry."

The couple was preparing to move. A year ago, Honey became the registered owner of a property in Toronto's Forest Hill neighbourhood. The Shermans planned to build a new home there.

They recently put their North York house up for sale. It was the real-estate agent who found their bodies.

With reports from Andrew Willis