Who is Leonard Winstone? Louis Tobin considered him a trusted attorney. Marilyn Tobin thought of him as a friend. As it turns out, he’s neither. He’s a conflicted con man with an abundance of family issues—an unlikely role for an actor who’s best known for his work on Saturday Night Live and Father of the Bride films. Nevertheless, Martin Short proved to be another brilliant casting choice! Josh Payne fills us in on the details.
Leonard Winstone is Louis Tobin’s fiercely loyal attorney. Years earlier, Tobin took a chance hiring a relatively untested Winstone, who has been with the family ever since. When Patty deposes the Tobins or presses them for documents, it’s Winstone who defends them at every turn, acting more like a devoted son to Louis than a legal shark. He even helps Louis’ wife Marilyn with her passion project, a charity for impoverished African children. Midway through the season Winstone’s father shows up, revealing Winstone isn’t a lawyer at all but a sophisticated con man. When he insists he’s loyal to the Tobins and not running a long con, Winstone’s father blackmails him—threatening to unveil Winstone’s shady past unless Winstone pays him off. Around this time, Louis’ son Joe learns the truth and excoriates him for lying to the family. Winstone decides to cut a deal with Patty; he’ll turn on the Tobins in exchange for his own immunity. But the deal fizzles in the wake of Tom Shayes’ death and Winstone quietly vanishes.
This was the last major role cast for Season 3. Martin Short was a Damages fan and knew the show pretty well when his name was mentioned as a possibility. As excited as the producers were to work with Martin, he didn’t have much dramatic work to refer to. Most of his career consisted of comedic work. In another example of casting against type, the producers took a risk that paid off handsomely. Early on, we planned to make Winstone responsible for the genesis of the Ponzi scheme. After watching dailies, we were concerned the audience would assume Winstone was behind the whole scheme, so we changed the story. That change wound up giving Martin a more emotional story that he played beautifully.
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