Just as Apotex was taking off in the late 1980s, Mr. Sherman unexpectedly reunited with the four Winter boys. They had not fared as well. A couple had turned to drugs and one later died of an overdose. None of them had gotten much from their father's estate. They were entitled to about $330,000 each from the sale of Empire but their adoptive parents spent most of the money and the boys blew through the rest when they turned of age.
After meeting them by chance through a mutual friend in 1988, Mr. Sherman became a benevolent cousin. He bought them houses, gave out cash and provided loans for an assortment of business ventures.
At one point, the boys began asking questions about Empire and they eventually came across the purchase agreement that they alleged contained provisions Mr. Sherman had ignored, including providing them with financial security. They also alleged that Mr. Sherman used the assets of Empire to create Apotex and had not properly compensated them. In 2006, they sued, demanding an ownership stake in the generic drug giant. "Losing our parents at such a young age is tragic, but what happened after their deaths is unbelievable," Kerry Winter, one of the orphaned boys, said in launching the lawsuit. "Barry's father died when he was young, and my dad took him under his wing and taught him the family business. It's disappointing that we're fighting this way now."
The legal fight turned ugly, with allegations flying that Mr. Sherman had plotted to kill Mr. Winter and that he used handouts to control the cousins. Mr. Sherman hit back by calling in their loans and moving to seize their houses. The suit finally ended last September when Ontario Superior Court Justice Kenneth Hood threw out the case, ruling that "the claimed interest in Apotex was wishful thinking, and beyond fanciful."