Boardwalk Empire, Season 4, Finale
Paul Schiraldi / HBO

Unlike previous seasons, season four in tumultuous flux. There's no neat resolutions. Was that a conscious decision?
Yes, we didn't necessarily want to wrap everything up in a bow. At the beginning of every season Nucky and his people are presented with a set of problems and in episode 12 everything's wrapped up neatly and they go off into the future. Life isn't always like that and certainly we didn't want our TV show to get to the point where you understood the rhythms of the show. You'll say, "Well, surely the Northeast storyline will end and everyone’s problems will be wrapped up one way or the other" and it was conscious that we didn't want to wrap things up. We wanted to go out on the feeling that you were a little off kilter and certainly some things did come to a very conclusive resolution [but] Chalky’s situation, Nucky's situation were not really so clear.

"In his heart Richard Harrow knew this is not who he is anymore and unfortunately he paid the price for it."

I suppose that's hard to do if you're living season to season like some shows.
Well, that was easier because we knew going into it we would be coming back, so that made it an easier choice. What I would hate to have happen is say we didn't resolve the story and than we find out we're cancelled. As a viewer I would be furious, I'd be like, "Wait a minute I didn't get any closure!" I certainly want to know how much time we have to tell what I want to tell as a complete story. 

I wanted to zero in on Richard Harrow and why of all the characters , he had to meet his fate? I had such mixed feelings about it, maybe that's part of the intention. I really was crushed by his death and I suspect a lot viewers were.
HBO just cut together a two minute in memoriam reel of Richard Harrow and I was welling up at the end of it. Wow, his character really struck a chord with people.
We just felt like Richard's story line had come full circle. We really didn't know where we would go with him beyond this—the idea that ending last season where he spent the whole season falling in love and getting away from the idea that he was going to kill anybody again. And than having to pick up the gun again and save Tommy made him feel unworthy with Julia and the Sagorsky. And it sent him into a downward spiral where he went off and of course, where we pick him up with him this season as a killer for hire.

By the time he gets back to his sister in Wisconsin she tells him he needs to call himself into account, we knew at that point that if he were to pick up a gun again that that would be one step too far and we knew inevitably as the story was plotting out that Richard would be the key to solving Chalky's problem at the end. Of course it took a tragic turn. Once he picked up that gun again that that was going to be the end of him emotionally and quite literally.

Than the idea of paying off the whole scrapbook angle of that family that he's trying to create for himself, that home and giving him ultimately, at least in his mind, full closure and bringing him full circle is sort of something that was interesting for us. He almost got there, he got very close and that was where we felt it was the most powerful way to take him out. 

It's always a big theme, but family's such a big one this season. How does the writing work? Do you guys decide which themes to explore? Are there ones you want to tackle in the future?
Yeah, a little bit. The whole idea of Nucky's quest to have a son: this has been something about who he is since the pilot. The idea of the baby that he lost and trying to have Jimmy as a surrogate son and it turns out he's got a surrogate son right there in his nephew Willy who we introduced at the end of last season. 

We knew he would be growing into college age and that would be a great catalyst in terms of a problem between Nucky and Eli. So we just started to just riff on that story, what might it be and what could happen with Willy away to college. It takes off from there, but one thing kind of leads to another. Story wise you start to connect dots and one story overlaps another and we start to realize that, "Okay if Wily got into trouble at school that would be an inroad for the FBI agent because he could use that as leverage against Eli trying to get Nucky." It's a lot of sitting around a table and putting the puzzle pieces together.

Boardwalk Empire, Season 4, Farewell Daddy

Richard's storyline is a bit separate from everyone else's and he gets caught in the cross hairs of that puzzle.
It's things that get set up in earlier seasons that come back to pay off. You realize that Richard did have a relationship with Chalky—he and Jimmy delivered the Klu Klux Klan guys to Chalky so they were aware of each other. Certainly the idea that in trying to fight Gillian in court Richard would need a job and the one person that he knows he can go to to get a job is Nucky. And he reintroduced himself into that world and of course you don't get involved with Nucky and Chalky without dipping your toe into the gangster world. So Richard served a purpose for them as well as a guy that you know could shoot an ant from 500 yards away, or at least that's what they thought.

Thematically then, it's pretty brilliant he loses his nerve and it all falls apart for him.
It all added up. The idea that he had left that life behind. His hand had been injured earlier in the year, I think in his heart Richard knew this is not who he is anymore and unfortunately he paid the price for it.

Is cruel fate a theme you play with by being in this mob world? 
Well it's all part of the theme of greed, ambition, power, corruption; the pursuit of money at the expense of everything else .Early on in the season Nucky says to Patricia Arquette's character that before prohibition he was a corrupt politician and a run of the mill crook and he was happy and than Prohibition came along and he wanted more and more and than more wasn't enough. That’s a big theme of the show, the whole idea of when is enough enough?

Power becomes too seductive for people. Certainly the idea of the fast money that was available during prohibition—it made millionaires out of a lot of people and it ruined a lot of people.

Boardwalk Empire, White Horse Pike, Season 4

How long can the show go on? Do you have an exit strategy? Would you go on 15 seasons if HBO let you?
No. For me it's a different model now it's not about, "Oh gee we have to hit x number of episodes to get it to syndication," and it's so much more free. For us the story will end when we feel like we brought Nucky full circle. Those are the conversations we're having now. Where are we going? Do we see an end in sight here? That's the debate we're having now every day with each other. Talking about it and again it's not about we want to get seven years out of this thing or six, or whatever. It's let's tell the best story possible and when we're done we'll move on and tell another story. It's much more akin to the British model and I think you're better off for it. It makes for a better story. So for us really it's a question of when does Nucky's story come full circle?

So you haven’t gotten there or mapped out all of that yet?
Not yet.

If you had to ballpark it how many more seasons would you like? Two or three?
I couldn't even say at this point, I really can't. That's exactly what we're talking about right now with HBO. If you start to feel like the series is treading water, to me that's the worst thing: you're just trying to keep this on the air. I'm really glad we don't have to do that.

In terms of surprises and twists: Jimmy Darmody's death was such a big move. Do you guys think in terms of surprises? Or are you just organically spitballing it and it comes together?
It's a little of both. We don't set out to say, "What's the biggest mind fuck we can pull?" But that said, it's all part of entertaining storytelling so for me it all starts from truth. What feels right, what is true to the characters and [whether or not] it feels phony. For me it starts with truth and killing Jimmy that season felt like the truthful end to that story. For Nucky to not kill him would have felt like the cheesy Network TV version of telling that story. "Oh gee at the last minute Nucky forgives the guy."

For more from this interview, check out Winter talking about his screenplay work on Martin Scorsese's "The Wolf of Wall Street."

Boardwalk Empire, Playlist only, do not use, Season 4, Finale
Paul Schiraldi / HBO