Terence Winter Talks Tulsa King Season 2, Keeping Stallone Front and Center, and Building on Cast Chemistry

It’s not every day that you get to sit down with someone like Terence Winter, the mastermind behind Tulsa King.

A veteran of shows like The Sopranos and Boardwalk Empire, Winter has proven time and again that he’s a force to be reckoned with when it comes to gritty, character-driven dramas.

And with Tulsa King, Winter has created yet another gripping world led by none other than Sylvester Stallone. As we gear up for Season 2, Winter is ready to dive into what’s next for Dwight Manfredi and his expanding empire.

After a wildly successful first season, many fans have been left wondering: how do you top that?

According to Winter, the answer is simple: “You keep Stallone front and center.” He continues, “We had one of the greatest stars in the world at the helm of it, so we kept him on the show.” No-brainer, right?

But it’s not just about having a megastar leading the charge. Winter has woven a rich tapestry of characters around Stallone, and in Season 2, those characters get even more room to shine.

“I think we created this world where we introduced not only Sly’s character but this really wonderful ensemble around him.

“And I think just following that storyline and those adventures and the deepening of those character interactions will certainly hopefully keep the show on the same track, if not better,” Winter explains.

So, what’s the secret to keeping viewers hooked? For Winter, it’s all about chemistry.

“You put Sylvester Stallone and Jay Will together, and they were just out of the gate incredible together. But then you’ll throw Martin Starr together with Max Casella, and boom — there’s this alchemy that happens,” he enthuses.

That on-screen magic is what makes the show more than just another mob drama; it’s a layered narrative where unexpected character pairings create something unforgettable.

Speaking of drama, the finale of Season 1 left Dwight in a precarious position, both legally and personally. And it’s clear from Winter’s comments that the fallout from those events will play a significant role in the upcoming season.

One of the most intriguing dynamics to watch will be between Dwight and Stacy, the ATF agent who turned on him.

Winter notes, “From her perspective, she really didn’t know how this was going to go over with him. Obviously, she was in a bind. She had a metaphorical gun to her head and did it.”

He adds, “Now that he’s out, she knows him but doesn’t really know him. What she does know is that he is a gangster, and he might be looking at a very long prison sentence again.”

This nuanced take on character motivations is classic Winter, and it’s one of the reasons why Tulsa King resonates so well with audiences. Dwight may be a gangster, but he’s not your run-of-the-mill mobster.

After years behind bars, he’s introspective and takes a more measured approach to people, sizing up their character before making judgments.

As Winter puts it, “I think Dwight treats everybody with respect until they don’t deserve it. And the second they don’t deserve it, he acts accordingly.”

But don’t think for a second that Dwight is going soft. With Neal McDonough and Frank Grillo joining the cast in Season 2, Dwight is going to face some serious threats.

“Neal McDonough plays a rival businessman and also slightly a bit of a romantic rival as well,” Winter teases. “He’s kind of got a soft spot for Dana Delany’s character.”

And let’s not forget Frank Grillo, who portrays a rival mob boss from Kansas City. Winter reveals, “He is obviously not thrilled to learn that there’s another guy in the vicinity doing the same job.”

With so many new faces entering the fray, Dwight’s carefully built empire is about to face its toughest challenges yet. And it’s not just external forces at play. Winter hints that Dwight’s expansion into legitimate business ventures might not go as smoothly as planned.

“In a perfect world, he wants to be legitimate, but he’s got very limited conflict resolution skills,” Winter says with a laugh. “He’s kind of a bull in a china shop when it comes to normal business tactics.”

The underlying tension of the show — whether Dwight can truly go legit or if his criminal past will forever haunt him — remains a central theme. And in Season 2, those stakes get even higher.

“Sometimes the impulse as a gangster is to sort of do the wrong thing or say the wrong thing, and you kind of create your own mess,” Winter admits. “We’ve got a little bit of a mess that goes on as the season progresses.”

For those of us who can’t get enough of mob stories, Winter promises that Tulsa King will continue to deliver.

As Dwight expands his crew, trust becomes a significant issue. “In the mob, you don’t really ever know who you can trust,” Winter points out. “Even hardened gangsters who swear an oath of silence have flipped on each other.”

So, will Dwight’s growing empire come crumbling down from the inside? Only time will tell, but Winter isn’t giving too much away. “Stay tuned,” he says with a grin.

One of the most delightful aspects of Tulsa King is its ability to blend drama with humor, and Winter attributes that to the very nature of the characters he’s portraying. “A lot of mobsters are very funny until you owe them money,” he jokes.

But beyond the quips, these characters have depth. Winter notes that many real-life gangsters have loved the show, especially the way it portrays them as fully realized people.

“They’re not all just one-note thugs,” he says. “They’ve got opinions about the world just like you and I do.”

So, what can we expect from Season 2?

Winter sums it up perfectly: “Season 2 is an extension of Season 1 in the sense that there is action, comedy, and great interactions between Dwight and his crew that everybody loves. And I think everybody will be really, really pleased with how it plays out.”

With an all-star cast, new rivalries, and a storyline that promises even more twists and turns, Season 2 of Tulsa King is shaping up to be bigger, bolder, and even more explosive than the first.

As Winter advises: “Stay tuned.”

Tulsa King Season 2 premieres on Sunday, September 15 on Paramount+.

We’ll be reviewing every episode, so don’t be a stranger!