'Boardwalk Empire' Boss on the Awkward Email That Killed Off Michael Pitt

Terence Winter
Brigitte Sire

“'You’re out of your mind to leave your job as a lawyer. Who do you think you are?'" Winter recalls as the worst advice he ever got. "I thank God I was such a terrible lawyer that I really had no choice."

Most fans found out about Jimmy Darmody's (Michael Pitt) Boardwalk Empire death when Nucky (Steve Buscemi) unceremoniously shot him in the face at the end of the second season. But Pitt found out in an e-mail.

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Series creator Terence Winter, speaking during The Hollywood Reporter's drama showrunner Emmy roundtable, says that he did try his hardest to give Pitt proper notice -- but technology got in the way.

"I always knew he would die at Nucky’s hand," Winter says of the series' feuding gangsters. "In plotting Season Two, it became clear that if we were going to tell this story honestly, it was going to happen at the end of the year. He was such a huge character, and we love Michael. It was one of the hardest decisions I’ve ever had to make as a writer."

The move was something Pitt had braced for. He asked Winter early in the series if he had plans to kill him off -- something he eventually confirmed after a botched conference call with executive producer Martin Scorsese.

Winter says that Pitt, in upstate New York on a fishing trip, kept losing cellular service and falling off the call. After several attempts, the busy Scorsese had to get back to work and told the showrunner they didn't have time to break it to him softly.

"Marty was like, 'Let me just e-mail him.'" recalls Winter. "I said: 'We can’t e-mail. We have to have this conversation.' But we couldn’t get him back on the phone. So ultimately, I felt horrible, but I had to send him an e-mail: 'I don’t want you to get the script and read this, but you sort of knew where this was going.' He was totally fine with it."

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Pitt just requested his character go out "in the worst way possible" -- a request he shared with another actor Winter famously dispatched. While writing for The Sopranos with David Chase, Winter remembers how it went down when they decided to finally (and gruesomely) kill Joe Pantoliano's Ralph Cifaretto.

"Joe Pantoliano made that same request on Sopranos," says Winter. "He said, 'I love being on this show, but if you have to kill me, please take me out with a bang.' We said, 'Done.'"

Patoliano's final moment on The Sopranos came when he was graphically decapitated by Tony (James Gandolfini) during the fourth season.