‘Lucky’ Creators on Those Finale Deaths and Killing Drew Starkey

SPOILER ALERT: This interview contains major spoilers from “All Good Things,” the finale of Apple TV’s “Lucky.”

Luciana “Lucky” Armstrong (Anya Taylor-Joy) has just pulled off one last con on the most important person left in her life: her formerly incarcerated father, John (Timothy Olyphant).

In the series finale of “Lucky,” the titular con artist pulls off a final scheme to win freedom for herself and her father from notorious gangster Wayne Whittaker (William Fichtner) and his dangerous underboss, Priscilla Masterson (Annette Bening) — who also happens to be Lucky’s disapproving mother-in-law. During a tense in-person meeting meant to hand over the $10 million she and her late husband, Cary (Drew Starkey), stole from Whittaker at John’s request, Lucky drops a bombshell: Whittaker had been secretly working with FBI agent Kershaw (Eric Lange) to track Cary, a betrayal that directly caused Cary’s fatal car crash in Episode 4. (Cary is also Whittaker’s biological son.)

That revelation instantly jeopardizes Lucky’s tentative deal with FBI Agent Billie Rand (Aunjanue Ellis-Taylor). Billie had agreed to give Lucky and her father immunity, but only if Lucky could deliver the evidence needed to lock Whittaker up permanently. Listening in from a nearby water tower via a wire, Rand realizes Kershaw’s connection to the plot and holds him at gunpoint, sparking a fierce brawl between them. Meanwhile, on the ground below, Whittaker forces Lucky’s hand. Knowing that he needed a back-up plan, Whittaker’s men kidnapped John from his hotel room and beat him up to make Lucky reveal the crypto seed phrase needed to unlock the stolen $10 million.

Marissa Stapley gave you her blessing to take creative liberties with “Lucky.” In hindsight, what do you think was the hardest part of this adaptation for you to crack?

Jonathan Tropper: There was the density of story in the book that I knew we would not be able to fully carry over into a television show. So it was breaking down: What’s the essence of the story? What’s the essence of the characters? What to keep from the book, what we would have to jettison, and then what we would have to invent to make it work in seven episodes of television — I certainly hadn’t cracked that before Cassie came on, and we cracked it together over time.

I had been able to write the pilot because that’s such a contained piece, but then figuring out what we were keeping, losing, and inventing beyond that was a struggle because we wanted to be really respectful to the themes and characters of the book. At the same time, it was like, “How do we convey this really complicated woman, and this really complicated father-daughter relationship that formed her? How do we convey that in a really taught thriller without having to tell all the backstory that’s in the book and without having to go into all of the flashbacks?” If we had 20 episodes, we could have done it, but how are we going to do this in seven or eight episodes? I think that was the biggest challenge.

Cassie Pappas: The things that we invented or added that were not in the book were merely to help stakes and propulsion. So Agent Billie Rand didn’t exist in the book, but we knew we wanted literal heat at [Lucky’s] back chasing her down. I also like the idea of two women locked into [a dynamic where] neither one of them knows how to do anything else. Rand only knows how to hunt and find you, and Lucky only knows how to run.

Tropper: We might’ve mentioned Pacino and De Niro in “Heat” a few times.

Pappas: It’s this good guy/bad guy trope that we see, but I don’t know that I’ve seen two women locked in that dynamic. I was really interested in exploring, “How do women play that game differently?” because we’ve definitely seen men do it over and over. As we got into it, we realized, “So we’ve got a woman on the run, a female FBI agent chasing her, and a female mobster chasing her as well. But each one of those women also had a man above them — you’ve got Kershaw at the FBI above Rand, you’ve got John above Lucky, and you’ve got Wayne Whittaker above Priscilla.” That was a cool metaphor of wanting each one of them to shatter a glass ceiling of sorts. And by the end of the finale, each one of those women do.

You chose to flesh out Lucky’s relationship with John, but you opted not to explore Lucky’s relationship with her mother, apart from a throwaway line in the show that suggests Lucky’s mother either died a long time ago or abandoned Lucky as a child. Why did you choose to focus on one relationship over the other?

Tropper: The father-daughter relationship was, to us, the heart of this show; the reason for doing the show was really to explore that. In this show, we wanted Lucky’s search to be her way out. It’s not about figuring out who her mother is; it’s about figuring out who she is. She’s never been given the opportunity to actually know who she is. So the search for a mother felt like it muddied the waters of what her throughline is, which was really a search for herself.

Pappas: We both agreed that it made the stakes more clean if John is all she’s got, if she’s like, “This is all I’ve got in the world. He’s taught me how to live in this world the way he lives, and that’s all I know. I don’t know how to be vulnerable, I don’t know how to be empathetic, but I do know how to lift your wallet.” So I think there’s something interesting about her being able to be like, “My mom is dead, and that’s not even in the picture.”

Anya Taylor-Joy was attached to star and executive produce this show long before you boarded the project as co-showrunners. What notes did she give during pre-production that ultimately influenced the trajectory of this story? Did she feel particularly strongly about any part of Lucky’s arc?

Pappas: She felt really strongly about Cary and their relationship. She felt very, very strongly that, when their parents went away to prison, Lucky and Cary got a taste of life outside of this criminal lifestyle. It was very important for her father to be the one that drags her back in, and that she didn’t want to be [involved in crime] when we meet her in the life. Because in a way, it creates a great underdog that you’re rooting for her to get out.

Tropper: It’s pretty much a nonstop chase. She really wanted to make sure we were taking the time we needed for the character, and not just having her literally on the run for seven episodes without time to stop, explore different facets of what she’s doing, and slow down for the personal moments. [She wanted to explore] both the fear and the frustration of the con, and also the joy that she still feels against her better judgment when she pulls off a good con. She wanted to make sure that the chase was never at the expense of the character.

How did you think about using those action sequences to reveal more about what is going on internally with Lucky?

Tropper: It’s always about where she is on the journey. So, for instance, in Episode 2, when she ends up with a grandmother and her two grandchildren in this very domestic setting, even as she’s conning them, you’re getting a sense of her seeing a life she never had — a mother figure, children, a dinner table, that kind of love and stability that she never had. So that’s what informs that whole episode. And then you go to Episode 4, which is this really high-octane car chase after she and Cary have found each other. But at the same time, while all that’s going on, where she’s really resolving her relationship with Carrie is during that car chase. So that whole car chase is the vehicle — no pun intended, or maybe pun intended, I don’t know — for her to resolve her situation with Cary literally at the last possible minute because then he dies. So I think it’s always story-formed. We just sit there and we think about: Where are we in the story? What is she running from or running to, and how do we express the character within that?

Why did you choose to kill off Cary as early as you did in the show?

Pappas: I didn’t realize how avid Drew’s fans are until we killed him. I think that we thought about Cary as level one of the lessons she needed to learn, which was “I’m repeating a pattern that is similar to my dad, but I’m doing it with my husband.” So when we get him out of the picture, then she can look at who she really needs to get out from underneath is her father. It was really servicing that more than anything else, unless Tropper has a thing against “Outer Banks” fans.

Tropper: No! I am shooting with an actor from “Outer Banks” today. [Writer’s note: Samantha Soule is guest-starring as a lawyer in an episode of Tropper’s “Your Friends & Neighbors” Season 3.] But it’s also the fact that we really always firmly believe that for Lucky to start the next part of her journey at the end of our show, she has to do it alone. She has to be freed from everything, and there have to be painful sacrifices for redemption because she’s not innocent, necessarily. We always knew that the last shot of Lucky was going to be Lucky alone stepping into a new life. So if she’s running off with her father or with Cary or with the money, she hasn’t fully extricated herself. We knew [Cary’s death] would be shocking, but we gave viewers the satisfaction of knowing that Cary had not intended to really leave her hanging.

Pappas: I also think just narratively speaking, it always signals to the viewer that nobody’s safe.

Lucky was born into this life of crime, but what intrigued you about the way she has learned to justify her actions? How does her moral compass bend over the course of the season as she wrestles with the consequences of her actions?

Pappas: I think that’s what Episode 5 is really about. She’s on the run [in Episodes] 2, 3, and 4, and the run keeps getting more propulsive into a car chase sequence where Cary dies. It’s after Cary’s death that she has to reckon with herself and the reality that her cons have consequences. It starts with that grandmother who was injured in the car crash, and she pretends that it’s her grandmother Ruth. But she has to look at that woman and remember, “Oh, that woman is injured because of me.” And then when the nurse asks, “What’s this woman’s medical history?,” she doesn’t have any answers. I think each one of these moments are like a blow to her.

By the time that she’s sitting with that stranger at the bar in Episode 5, she goes into the routine of, “Here I go, I’m going to tell you this lie about how the reason I’m wearing these clothes is because the bellman got my bag wrong.” She stops and, for the very first time in her life, she chooses to be honest with someone. I think that’s truly where her moral compass starts to shift. The title of the episode is “Are We Bad People?,” because when she’s a kid, she asks her dad the same question. So if she’s been ruminating on that question her whole life, now as an adult, she gets to face herself and go, “I really hope I’m not a bad person. I don’t want to be a bad person. If I am, I don’t want to be.”

Tropper: Her moral compass was bent before the show started; it’s been bent her whole life. So going into this, she has a skillset and she has a certain perspective of the role that’s been shaped largely by her father. From Episode 1, she’s doing things in a morally gray area, and that’s where she’s lived her whole life. It’s the unbending of her moral compass over the course of the season that gets her to where she needs to be.

With any great crime thriller, you need a high dead body count — and two of the most satisfying deaths, Kershaw and Whittaker, happen in the finale. How did you settle on who died in the finale? Did you ever consider killing off, say, Priscilla or anyone else?

Tropper: We always knew that this is a show about three women who are pitted against each other. In a sense, there are three heroes and villains, and there was never a question that [the women] were not expendable, whereas everyone else around them was, depending on how the story worked.

Pappas: I think pretty early days, Jonathan and I knew that Priscilla was going to shoot Wayne, and that it was going to be because of the love that was shared between her son and Lucky.

While there is still a tremendous amount of love between them, Lucky makes a clean break from John by the end of the show. What do you imagine their individual lives will look like after the screen cuts to black?

Pappas: I think John can’t help himself. He can’t help that he’s going to walk into a room and see a con and go back to his hustle. That’s just who he is. And for Lucky, I think she’s going to live a life that is on the straight and narrow, but free, and [she’ll] figure out who she really is without all the masks that she’s been wearing her whole life.

Tropper: I would like to think that after a number of years of figuring herself out and learning to trust people and trust herself in certain situations, ultimately, she may want to have a child to give a child the life that she didn’t have.

Pappas: In the [writers’] room, we did talk a lot about how criminals like this, whether it’s “Breaking Bad” or “Better Call Saul,” you walk into a room and you just see the world a certain way. That is how she sees the world, so I don’t think that she can unsee the way her father taught her to see the world. She’s probably always going to walk into a room and see a mark, but I believe that she can choose to not con that person. It’s like an alcoholic walking into a bar and not having a drink.

“Lucky” was always billed as a miniseries, but in the current TV landscape, nothing in success ever really seems to be limited anymore. Did you ever toy around with a different ending? Did you ever think about extending the story beyond seven episodes?

Pappas: No, we wanted to make sure that we tied up all the loose ends and that it was a satisfying ending to a limited series.

But Marissa is currently working on a sequel titled “No Such Thing As Lucky,” slated to come out in the fall of 2027. Would you ever adapt that book?

Tropper: We really poured our hearts into a one-and-done situation and we are both working on other things, but you never say never. Even from a purely business standpoint, I think the logistics of pulling this cast back together and doing this again would take a lot of doing. I think we would have to convince ourselves to a large extent that there would be a story worth telling, because there’s something so compelling about the resolution of these relationships in this one. And if the second one was just kind of like, “Lucky gets sucked back—”

Pappas: “And goes on the run again!”

Tropper: Yeah, I don’t think it would carry the same weight. I think it would feel very much like a business decision. So right now, I personally don’t see us doing that.

This interview has been edited and condensed.