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Showrunner Terence Winter on Boardwalk Empire’s Season-Four Finale

[Spoilers ahead] Boardwalk Empire just closed its vastly improved fourth season with a grace note: Richard Harrow, the disfigured and tortured vet-turned-assassin, finding peace in death. ("That's him in heaven, or this is his dying wish," showrunner Terence Winter explained. "He was made whole in death.") And with this beloved character's end, the chessboard of Boardwalk alliances and hostilities has been redrawn, with Harrow and Knox/Tolliver dead, Van Alden firmly in Capone's corner, Margaret in league with Rothstein, Dr. Narcisse and Gillian Darmody in custody, and still others in exile. What does this mean for the show going forward? Winter called up Vulture to chat about the finale and his initial thoughts about season five.

I'm a little devastated that you killed off Richard Harrow.
I know, I know. [Chuckles] It's devastating for all of us. That was a really tough decision.  But it was the most powerful way to bring that storyline home. HBO just sent me a two-minute Richard Harrow in memoriam reel, and I got emotional watching it. I'm sitting here, feeling like an idiot, crying watching this thing. But people in the gangster world very rarely get out of this business and die in bed, and we knew Richard was running out of road.    

With Richard's death, Tommy in another family's custody, and Gillian in jail for the murder of her son's lookalike Roger, does that mean the end of the Darmody storyline?
Well, it's certainly something we want to explore further, but Gillian is really the lynchpin between Nucky and the thing that Nucky became. The Commodore said, "Bring me that young girl," and Nucky did it. Arguably, that's the pivotal event when he sold his own soul. So it's not accurate to say there would be no more use for her. She's really the key to Nucky in a way. All the things that happen to Nucky, the good things, the bad things, they all stem from that event. Gillian is the reason.

Nucky doesn't seem to be aware of that. She doesn't seem to weigh on his mind, even when he's holding the newspaper with the headline about her trial.
Look, Gillian is a horrible person on so many levels, but she became that person for a series of reasons, and Nucky was a large part of that. I think in Nucky's quiet moments of self-reflection, he could probably cop to being the cause of some of that. On the surface, he doesn't let that sink in and won't admit it.

The series of events leading up to her confession, the way Ron Livingston played her, the steps along the way, was amazing. First he sees how good of a liar she is on a "date," where they pretend to be married, and then he sees how she reacts when Roger's name comes up, seemingly by accident.
Just to start to get her rattled, yeah. That whole storyline was inspired by two separate cases I'd read about that happened at the turn of the last century, both involving detectives, one of which may have been a Pinkerton agent. A female Pinkerton agent sort of got into a relationship with a guy who they knew murdered somebody, and gained his trust, and then pushed him away and said, "I feel like you're holding back on me. I sense that there's something you want to tell me." Eventually the guy confessed, and that's how they caught him. I thought, Wow, that would be a cool thing to do for Gillian. We could see her fall in love, hear about her back story, and then of course pull the rug out from under her. And Gretchen [Mol] was heartbreaking. Coming into the season, so many people despised that character, and now people are feeling sorry for her, because Gretchen knocked it out of the park.

I find it interesting how harshly Gillian is judged because she killed Roger ...
And slept with her son. But hey, nobody's perfect! [Laughs]

Right, but the people in her world don't know that. So in the custody case, it's like, which is the lesser of two evils? Richard Harrow was good to the boy, but he's a trained killer. Gillian has a much smaller bodycount.
[Laughs] People are so in love with Richard, but he's killed like 89 people! "But he's a great guy!" I know he's really cute and cuddly like a puppy, but he's got a screw loose! But you drown one tourist and run a whorehouse, and suddenly you're a bad person. You know what, she should get an attorney to say all these things and get her out of jail. [Laughs]

Were you ever tempted, with both Ron Livingston and Stephen Root in the cast this season, to have an Office Space moment?
Yeah, we talked about it: Is there any way we can get these two guys in a room together, and then have a stapler missing? [Laughs] I felt like such a douche, because when I met them, all I wanted to do was talk Office Space! I just became a total fan, you know? "I hate to bring the conversation to where inevitably everyone else must bring it, but can we talk about Office Space for a minute?" They were pretty good sports about it.

Now that Dr. Narcisse has become the FBI's informant on Marcus Garvey, are we going to see that play out? Hoover was obsessed with Garvey for a long time.
Yeah! If anything, Narcisse is now more empowered that he's got a friend in the FBI. Hoover very famously denied the existence of organized crime until the late fifties. And we thought, He obviously knew it existed, but what was going on there? And we were able to create our fictional version of this FBI agent Jim Tolliver who was the first guy to posit the theory that Hey, different criminals in different cities are working with each other. What if we arrest them all at the same time? But Hoover was much more interested in putting people like Garvey in jail, and organized crime was so big and unwieldy, and basically an unwinnable battle. So when Knox gets killed, it's easier for Hoover to just wipe that off the table and just say, "Okay, you're going to blame it on one of the Garvey guys, and we're going to make believe the other organized crime stuff never happened." So it was a fun way to introduce that story and dispose of it at the same time.

Because of the double agent ruse, Nucky didn't recognize even recognize who his antagonist was this season.
Nucky's series of distractions kept him from putting together that this baby-faced Prohibition agent was actually something much more akin to a fox in the henhouse, and it wasn't until late in the game that he started to realize that it was much worse than he thought. And there's certainly been a lot of shifts in allegiances, and a lot of the power dynamics have changed, and that's a lot of what we'll be exploring as we move into season five. The truth is, we're really at the beginning of that, but certainly Al Capone is a good example. Once Torrio retired, Al Capone became the Al Capone we all know and love — so moving forward, you're going to see Scarface, that guy. We'll probably jump a little bit in time, but I'm not sure by how much.  

Since you also wrote The Wolf of Wall Street, is that going to dominate your holidays this year, before you get back into the Boardwalk writers' room in January?
I'm biased, but even if I hadn't written it, I would tell my kids, "I'm canceling Christmas, Daddy's got to see Wolf of Wall Street!" [Laughs] Leo [DiCaprio] is completely unhinged in that film, and he just goes for it in a way that I've never seen before. There's a 12-minute sequence of him and Jonah Hill doing Quaaludes together that is unbelievable. I do Christmas every year, but it's only once in a lifetime that you get to do a Marty Scorsese movie. So that's it! Humbug!

Photo: Paul Schiraldi/Paul Schiraldi Photography