In the summer of 1988, Barry Sherman received an urgent phone call—from a prison in Oregon. On the other end was a familiar voice: that of Harvey Rubenstein, a notorious Toronto stockbroker convicted of fraud on both sides of the border. Though Rubenstein’s financial scams garnered plenty of headlines, few people had any idea his victims included the founder of Canadian generic drug giant Apotex Inc. Mere weeks before taking that call, Sherman had launched a lawsuit against Rubenstein, his former investment adviser, claiming he’d been duped out of millions.
Now the disgraced broker, recently extradited to the United States to face another slew of fraud charges, was asking for even more of Sherman’s money: US$100,000 so he could post bail. He told Sherman if he weren’t behind bars, he could focus his efforts on recovering his lost money. Sherman agreed. “I couldn’t see any benefit, from my viewpoint, of having him languish in jail,” Sherman later testified in a sworn deposition
The story didn’t end there. After Rubenstein pleaded guilty, Sherman agreed to loan him half of the $100,000 bail money so he could pay restitution to his victims. But when another creditor stepped forward to claim rights to the remaining $50,000, Sherman spent the next four years fighting in U.S. court to eventually recoup what, for him, was essentially pocket change.
That long-ago tale, excavated from thousands of pages of court documents, corporate records and charity filings reviewed by Maclean’s, reveals the paradoxes of a man whose brutal death is now being investigated by police. A hard-nosed strategic genius who built Canada’s largest pharmaceutical company, Sherman also conducted business with known criminals. He’d generously bail out someone in need—but often with a longer, self-interested view. He was a billionaire driven to litigation less by money than something more primal: a sense of righteous certitude that propelled him to prevail at any cost. (more...)
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