New Jersey has been good to Terence Winter. The Garden State furnished him with the inspiration and settings for two of the most iconic series in television history. Winter was a writer and executive producer for The Sopranos, and the creator of Boardwalk Empire. The Brooklyn born ex-lawyer sat down with EDGE Editor at Large Tracey Smith to talk about the two shows and their protagonists, reveal a nugget or two about the upcoming Boardwalk Empire season, and his upcoming film, The Wolf of Wall Street. What’s the key to writing a great series about crooks? Honesty…what else?

EDGE: Explain how you were able to transition so easily from The Sopranos to Boardwalk Empire?

TW: It might have looked easy but it wasn’t. There was a lot of research involved for Boardwalk that I didn’t need to do on The Sopranos. For example, on The Sopranos, because it was contemporary, I didn’t need to look up pop culture references, I knew the way people spoke, acted, and dressed. For the 1920s, it’s a whole different ball game. I needed to learn about World War I, I needed to learn about the Temperance Movement, I needed to learn about the year women got the right to vote—I needed to put myself in the mindset of characters who were born in the 19th century. So colloquialisms, what books did they read, what movies were out then required months and months of research before I was even able to begin to write the pilot. So even though they are a similar genre, and the characters cover some of the same territory psychologically, it’s almost a hundred years earlier, so the prep work was massive.

EDGE: One of the first things Tony said on The Sopranos was that he felt like he was coming in on the end of something. Steve Buscemi’s character in Boardwalk Empire, Nucky Thompson, is right there at the start of something.

TW: Right. Prohibition was the single event that made organized crime possible. That, more than anything else, was the impetus for criminals to start working together to make money. The interstate trafficking of alcohol made millionaires of criminals overnight, and enabled them to then infiltrate other businesses, and ultimately become organized throughout the country.

EDGE: How do Nucky and Tony compare as protagonists?

TW: In terms of their psychology, they both at their heart are depressed people, sort of searching for something that will make them happy. They are both very smart, both natural leaders, and both are ruthless. Tony’s fatal flaw is that he has a conscience. If he were more of a true sociopath, he wouldn’t pass out, wouldn’t have panic attacks, and wouldn’t care. Nucky, I think, is the same way. We’ve explored a little bit of the psychology of Nucky. We learn by the end of the first season that his wife lost a child very early on, and he is still haunted by that, and that he had a difficult relationship with his father. He’s trying to repair a broken childhood and to recreate a happy family life that he can’t quite seem to replicate.

EDGE: How did Steve become your Nucky?

TW: I’ve been a fan of Steve’s since a movie he did in the 90s called In the Soup. The moment I saw him I was just fascinated with this guy. I was lucky enough to get to know him when he directed a few episodes of The Sopranos that I wrote, and we became friends. Then, of course I got to work with him as an actor when he portrayed Tony’s cousin. I’ve seen everything that Steve’s ever done as an actor. I’ve seen him portray every possible color of human emotion, back and forth, every which way. So for me there was never a question of whether or not he could be convincing as Nucky. When we started to cast for the show, Martin Scorsese and I were talking about who is going to play the lead role. Our Nucky is based on a real person, Nucky Johnson. We fictionalized him as Nucky Thompson, so he’s a version of that person. But we realized since nobody really knew what the real Nucky looked like anyway, it didn’t really matter who we cast in terms of whether or not they looked similar. So Marty said, “Well, let’s just pick an actor that we both like. Who are people you want to work with?” I’m pretty sure it was me that said, “What about Steve Buscemi?” He jumped on it and said, “Oh my God, I love him.” About a week later, Marty called me up and said, “I can’t stop thinking about Steve Buscemi.” I told him I couldn’t either, and he said, “Let’s do it.” HBO was on board—their feeling was Wow, what an interesting choice. That was it. We were off to the races.

EDGE: Why didn’t you use Nucky’s real surname?

TW: I wanted the opportunity to take my Nucky into places where the real Nucky might not have gone. For example, I’m pretty certain the real Nucky didn’t kill anybody. I’m pretty certain he didn’t embrace gangsterism the way our Nucky does. Fictionalizing him gave me artistic latitude and allowed me to sleep at night.

EDGE: How difficult is it to develop so many characters simultaneously?

TW: It’s a massive juggling act. There’s a lot of plotting out, there’s a lot of characters on the show, we’ve got action taking place in several different cities—it’s a big, big, chessboard of characters. That’s the work that goes on in the Writer’s Room. It all starts with “What if?” If suchand- such happened, what would the result of that be? What’s the fallout from that? Where do we want to end up? I’ll come into the season and have a pretty good idea of where I want things to end by episode twelve, sort of like a roadmap. We’re gonna drive from New York to California—alright, well, how do we get there? Those are the story beats that bring us to various places, and it takes a lot of sitting around the table and talking and banging your head against the wall, and plotting, and figuring it out. Eventually, it all works, but it’s a big, big, juggling act.

EDGE: And now you have two new characters to blend in.

TW: Yes. Jeffrey Wright plays a character this season called Valentin Narcisse. He is a Doctor of Divinity who also happens to be the most powerful gangster in Harlem. He crosses paths with Nucky and Chalky in Atlantic City, and that is about as much as I can tell you at this point. If you know anything about Jeffrey and his work, he’s a phenomenal actor, just incredible. We were so thrilled to be able to work with him and have him on the show. The same with Ron Livingston. I’ve been a fan of Ron’s for years and years. He’s so versatile. His work on Band of Brothers, Office Space—I mean, he’s one of these actors that can do comedy, drama, anything in between. He becomes an acquaintance of Jillian Darmody’s, and has a really interesting storyline as well. I’m really excited about both of those guys.

EDGE: A lot of people were shocked when you killed off Jimmy Darmody at the end of season two, just as they were when Tony killed Christopher in The Sopranos. What’s involved in the decision that a major character has to go, especially a protégé?

Photo courtesy of HBO

TW: First and foremost, I try to write the show truthfully. I try to avoid making decisions based on what would be the popular choice, what the audience would want me to do, what the conventions of television would be, which is: You don’t kill your second lead on the show, a beloved character. As season two was playing out, it became really clear to me that if we were going to tell this story honestly, Nucky would kill this guy…and he would kill him immediately. If I were watching this and he at the last minute changed his mind and Jimmy got off with a stern reprimand, I’d say, “This is not true, this is a TV show!”

EDGE: It is a TV show.

TW: But I want it to feel real. I think over 60 or 70 years of TV history, we’ve sort of lulled our audience into a sense of complacency. People say, “Oh, well, they’re obviously not gonna kill this guy, I know it looks like they are, but they won’t, because he’s one of the stars of the show. So, of course, people couldn’t believe when we did it, which made me even more certain I’d made the right decision. The louder the uproar, the louder the outcry, the more I was convinced we did the right thing.

EDGE: You have some interesting projects coming up with Leonardo di Caprio, Martin Scorsese and Bobby Cannavale.

TW: In November, Wolf of Wall Street opens. That’s, as you said, directed by Martin Scorsese and stars Leonardo di Caprio. It’s the true story of a stockbroker named Jordan Belfort who, in the 90’s, made tens of millions of dollars a year as the head of his own stockbrokerage firm. He found a way to sell very inexpensive stocks to rich people. He sort of cracked the code, and he and hundreds of young brokers working for him made a fortune. It was just an incredible roller coaster, a wild ride with incredible amounts of money and drugs. Leo is terrific in it and, of course, we’ve got the master, Martin Scorsese, directing. I’m also working on another series with Martin Scorsese for HBO, this one involving Mick Jagger. It’s set in the world of rock music in 1973 New York City, starring Bobby Cannavale as a cocaine-fueled, A&R executive for a record company. That was the year that punk, disco and hip hop were all invented in and around New York City, a time of great change, of great upheaval in the city. I’m really, really excited about that project. Hopefully, the pilot will be directed in the early part of next year, and we’ll go into series right after that.

EDGE: Cannavale was like a bull in a china shop on Boardwalk Empire.

TW: Oh yeah! There was nobody better to play the Gyp Rossetti role than Bobby. He was great. I think we had one conversation about who that character is and what motivated him, and Bobby got it immediately and ran with it and became Gyp Rosetti. It’s so funny, because nothing could be further from the real guy. Bobby is just the sweetest, funniest, most gentle person in real life, and as an actor he can sort of give you anything. He can turn into Gyp Rosetti on a dime and then go back to being himself again—it was pretty amazing to watch.

EDGE: How many more seasons?

TW: I would love to do seven seasons all together. We’re starting down the homestretch in season four; whether or not we’re fortunate enough to get to do them remains to be seen. It all really is going to depend on what the public’s appetite is for this show, and HBO’s, of course. I would love to do three more years, I think that could take us to the point in Nucky’s story, and the point in history that I’d like to get us to. Hopefully, we’ll get the chance to do that.

EDGE: Are you a nostalgic person?

TW: Very much so. I love history. I am the family’s historian. I’m the one who archived all of the family photos and films, the genealogy and all that stuff. I love the idea of leaving that behind for my children, and grandchildren, and their children. I’d give my left arm just to read about what my great-great-grandfather’s day was like. “What did you do, where did you go, who did you talk to?” That stuff is fascinating to me. 

Editor’s Note: There are no short conversations once Tracey Smith gets you talking. For (a lot) more on Nucky, Chalky, Margaret, Richard and Van Alden—and the inside story on the brilliant “Pine Barrens” episode of The Sopranos—visit edgemagonline.com and read the rest of our Q&A with Terence Winter.