Teddy Wayne, THE WINNER

Teddy Wayne, THE WINNER

Zibby speaks with award-winning author Teddy Wayne about THE WINNER, a dark, explosive literary thriller about an unemployed law school graduate who gets a summer job as a tennis pro at an exclusive, old-money community near Cape Cod, and gives lessons (and more…) to a divorced woman twice his age. Teddy delves into the real-life inspirations for the setting, his character development process, and his interest in depicting class and privilege in this story. He also reveals that he is working on the screenplay for a potential film adaptation (!), describes his journey to becoming a writer, and gives his best advice to aspiring writers.


Zibby: Welcome, Teddy. Thank you so much for coming on Moms Don't Have Time to Read Books to discuss the winner. Congrats. 

Teddy: Thank you. 

Zibby: I devoured this book. It's so good. It's, oh my gosh, it's going to be such a hit. I'm just, I'm just calling it now in case you were unclear that that was going to happen.

It's so great. Anyway, why don't you tell listeners what it's about and we'll go from there. 

Teddy: So the winner is the story of Connor O'Toole, who's a young law school graduate who finds himself unemployed in the summer of 2020 during the pandemic. To make money, he takes a job for the summer as a tennis pro at an old money wasp community near Cape Cod.

While there, he starts giving lessons to a divorced woman about twice his age. She soon starts paying him for services that are off the court. I'll use euphemisms here. Soon after that, he begins a more age appropriate relationship with a girl his his own age, and complications ensue. And I won't get too far into it, but it gets very complicated for him.

Zibby: Yeah. I could not believe some of these twists and turns and the, first of all, the setting itself, like, I feel like I know exactly, I feel like I would be able to navigate around this whole cotter's neck, it's called, right? Cotter's neck. 

Teddy: Cutter's neck. 

Zibby: Cutters. Sorry. Cutter's neck. Cutters, right? They keep calling it cutters.

So first of all, you, like, put us in such a place. And then, Your characters are so incredibly real and like flawed, but so real, like how did you do that? Like, where did Connor come from? Where did the story come from? And what are the secrets to creating characters that are so vivid and real? 

Teddy: Well, the setting was the easiest in that it's based geographically almost, almost identically on a place my wife's family, extended family, has a summer place.

And so there's a community much like that. There's a quote unquote yacht club, which is a place where people swim, there are no actual yachts. There's a very extravagant mansion at the end of the, of the point, it's called, which is what Catherine, the older woman's house, is based off. So that part was easy, and we'd been going there for years, and I always thought that would be a great setting and backdrop for a novel, but I never knew what that novel would entail.

Then the pandemic hit, And I thought this is a really good setting to explore socioeconomic inequality in America, the kind of paranoia and anxiety that the pandemic brought on, even though the pandemic is there in the novel, it's kind of in the background, but it's, it's always lurking. And so that the setting was, was, was the easy part.

The characters were, you know, a little tougher as they always are. You want to start with individuals rather than types. So even though Both Connor and Catherine, I think, could be boiled down to a certain type. Uh, if you start with that, with that universal type, you'll get a stereotype. If you start with individual characteristics of them, Connor is a sort of a classic Horatio Alger pull yourself up by the bootstraps young guy who's, Raised by a single mom, his dad died when he was young.

He discovered an aptitude for tennis when he was young and that enabled him to get scholarship to college and so on. But then thinking about other things about him that would distinguish him like yes, he's a good tennis player, but he's not your classic lead. overpowering tennis player and not to get too in the weeds of tennis for this podcast, but he's what's known as a pusher, a defensive specialist who hits the ball back safely.

And that's maybe against the grain of what you'd expect for a novel about a guy who's good at a sport. You'd think they'd just be incredible. But in fact, He's not that good. He's just placed safe and steady and conservatively, and he wins through that. So that's this kind of example of, I think, a detail that I hope sets him apart from to stock a character.

Same with Catherine, of course. There's other aspects of her personality that I hope set her apart. And sometimes it's, you know, certain lines that people have said in real life that you remember and hang on to, and that you put in the mouths of characters, and suddenly they become that individual that you said that.

Zibby: Okay. Who said what? Let's just fill right now. 

Teddy: I'm very, this, this is, she got it all based on this woman, but a woman I'm very fond of who's older. Once when I was there in, in the real life Cutter's Neck. Last summer, in fact, I was, I got impromptu invited to a wine tasting. Sorry, it just sounds so ritzy about it.

I was dressed in like, you know, shorts and a t shirt, but I was, I was invited along. It's casual, it's a casual place, more so than Cutters actually is. I was carrying a, a seltzer, a can of seltzer, and also wearing like a baseball hat, you know, looked a little bit unkempt, but again, it's a casual place. As we started to go in, the, the woman, she's about 70, said, Maybe don't bring the seltzer, it's a little middle class.

And I always thought that was a great, and she, she apologized later and sent me a long text about it and was very abashed about it. But to say, call something a little middle class, I thought was a funny line that I put in the mouth of Catherine. Catherine was not at all based on this woman, whom again, I'm very fond of.

Zibby: I understand. I understand that this, if this woman is listening, it's not you. How is this different than your world and your, where you're from and your summers or whatever? Like, how did your wife's how has that been? Like, what was your story? 

Teddy: I'm from New York and, you know, the main difference is I'm like a secular Jew and just went to summer camp in the summers and, you know, have been around plenty of, of privileged people in my time, certainly.

This feels like a different culture completely. This is old money wasps and it's, it's a very much, uh, A different set of customs again, I think that middle class line wouldn't come out in places. I I'm from necessarily and you know, from things like as, as basic as men wearing pink Nantucket red shorts, which, which when I, I first saw when I came to this place and was sort of surprised by to see men wearing light salmon, salmon, pink shorts to the, the bigger issues of, of, uh, You know, inherited money and knowing that your life is completely set out for you.

And I think the, the complications that, that, that produces in some people, it leads to a kind of maybe slackerly laziness. They don't feel like they have to earn anything and so others, at least this kind of guilt that the girl he starts dating, I think feels. and a desire to make amends for it and to prove herself in her own right.

She's an aspiring writer. So there are a number of, of differences from what I've encountered, even if, um, you know, I've been around spaces of privilege that are somewhat comparable, if not quite comparable to this. 

Zibby: Interesting. So, do you have a law background at all, by the way? 

Teddy: No, I get asked a lot of questions.

The research was all, um, both my sister in law is a lawyer, but then I asked a DA that I know a lot of criminal law questions. Again, without spoiling too much, there's criminal law parts of this novel. And then a New York police detective I also asked a lot of questions of. 

Zibby: Well I am, you know, I don't want to give anything away either, but I feel like you're, you're gonna, I, you know, I don't want to say anything, but I was going to make some joke about, you know, but I'm not going to, so. 

Teddy: Real life experience, maybe, or. 

Zibby: No, no, I was going to make a joke just about like how you could cover your tracks in such a way, you know, I wonder like all the things that you've secretly done, you know, in your life, you know, it seems very odd thought out and I wouldn't want to be, you know. 

Teddy: I now have an idea of how to do it. I get a lot of questions about cell phones and what cell phones keep track of for you and in fact again without spoiling anything, the DA I spoke to gave me the idea for pretty much the final twist of the novel. Wow. And the detective has confirmed that that works and he in fact Texted me a couple weeks ago about a real life case of them doing the same sort of thing.

Zibby: Oh my gosh. 

Teddy: So that's you know, that's I guess another example of how you make it sound about character. It's a plot idea but talking to people who really know these things inside out and The D. A. said that not many people even know about this thing. Certainly, civilians don't, not even all cops, I think, know about this twist that, that occurs.

Zibby: Interesting. Well, to your point also about the societal class culture, you know, inherited wealth thing, you know, you have a scene where a bunch of, you know, The children, grandchildren, you know, the younger generation, they're all like sitting around, you know, talking about how they're getting out of work and their internships and, you know, just totally messing around and whatever.

And, you know, Connor is just sitting there being like, I cannot believe this, you know, just one of many moments where, um, Like, why does their life, why do they get to just, like, slack off when here I am literally, like, hitting a tennis ball against a wall and, you know, doing everything in my power to try to change my station in life, whereas they've been handed this and they're not even working hard.

Tell me a little bit about that. 

Teddy: Yeah, I mean, again, the real life inspirations are not nearly as bad as the characters in the book. So let me make that clear. But I think class is a very important subject that seems to get underwritten about in contemporary literature. I think about 100 years ago, it was written about much more when America was kind of discovering itself, getting a lot of money.

People started realizing social classes, a sort of new thing we've kind of reckoned with, and a lot of novels from that time. You know, 1890 to 1930 or even 1940. dealt with it. What I really think is the case is that because so many authors and editors and people in the book industry at large are kind of from like an upper middle class white background, if not strictly financially, then in social signifiers, everyone who writes a book now or edits a book or publicizes a book probably reads the New York Times and listens to NPR and so on.

I could run through the list of things there. And so, That's fine. That's what I do, too, but we shouldn't treat it as the default. I think we should interrogate that and interrogate what it means to not have all that much money or what it means to come to have a novel set in a ritzy summer place like this and not treat it like it's standard to have this kind of summer house.

But so therefore, due to the eyes of the character for whom this is all novel, it would those kind of differences would be most. obvious and stark, I think, when he's seeing his own contemporaries, people around his age who had their lives laid out for him. I think ultimately, you know, you don't want to, his, his mentor when he's younger tells him you don't want to be ranked one, number one in the world.

You don't want to be the top of the, of the, of the ranking. You want to be just below it. And be satisfied with that. Be satisfied with what you have. That's real happiness. That's real stability. That's real security because the people on top are always actually wanting more and more and more because they are afraid of losing their perch.

And so you want to be ranked, you know, in tennis terms, ranked fifth in the world, but be kind of satisfied with being fifth because it's still a great place to be, but you're not going to kill yourself and, and, and be, you know, ruined with anxiety that you're not number one, nor will you fear that everyone's gunning for you.

So. That's really one of the bigger issues Connor grapples with over the summer is he starts getting a little corrupted and wanting to become that number one slot. 

Zibby: I mean, do we really think that the number five slot, like who is it now? Like Medvedev or something like he's really happy about that. You don't think he's done it.

Teddy: I think sports, I think they do always want to be number one. I think in American class terms, maybe it's okay to be, you know, 90. sixth percent of income. I think it's a pretty good life. And if you're happy with it and don't feel like you need to get to the 99th percentile, you might be happier than somebody who's always on top working themselves to death and, and afraid that they'll lose it all someday because it's, it's all per, you know, premised upon just this sort of insane degree of, of wealth.

And it's, it's hard to keep up. So I've always thought. You know, even in non monetary terms, it's good to be ambitious because it does drive you, but to be too ambitious is its own type of poison. 

Zibby: So what does that say about your own ambition? 

Teddy: I've, I've, it's tempered somewhat because I have two young kids.

I go a long way. One of them, my five year old son, Angus, is another room. Now he's homesick from school. Oh no. Yeah, he's, he's fine. But, When you, when you have to start thinking about other people and can't just think about your own life and own career and own success, it goes a long way towards changing your ambitions from, I want to write the number one ranking novel, which is never going to happen anyway.

Two, I want to be the number one dad and I got a coffee mug that says number one dad. But you know, you want to be, you, you start caring more about other things beyond financial or reputational success. 

Zibby: That is very sweet. Well, I hope Angus stocks your cabinet with lots of number one dad mugs. What is your relationship like with tennis?

Are you a big tennis player? 

Teddy: I played as a kid a lot. I was on the high school team. I peaked at about age 15. I think I was the number one rank on my ninth grade JV team. And then by 10th grade, everyone had had shot past me. Something happened that summer. I don't know what it was. So I played a lot as a kid.

I still play occasionally now. just really in the summers. And like, I don't really watch it anymore. I used to be a fan of the sport too. I kind of stopped watching most sports at this point, but have always enjoyed it as a sort of, there's a literary poetic feel to it. There's something very beautiful about literally the aesthetic background of a tennis court is usually something nice visually about it, but.

The game itself, the slices, the spins, the angles. Um, I've always been closer to Connor, more of a pusher, but really more of like a, I don't know what you'd call me, uh, sort of like a junk baller in baseball would be the term. Somebody gets by with like weird spins and slices that confuse the other, the opponent, rather than actually being good at the sport.

But that, there's something fun about that, more of a tactical approach and figuring out How to win at the margins rather than, um, winning through playing well. There's a book we, I read, I think when I was younger, our tennis coach in high school loved this book called Winning Ugly by Brad Gilbert and I adapted various stratagems.

Zibby: Brad Gilbert was Andre Agassi's coach, wasn't he? 

Teddy: Was, and he kind of changed his game and things from that book showed up in the winner. Like how to play, you should play aggressively when you're when you're down 40 love in a game and you're. 

Zibby: Yeah. 

Teddy: Typically you think I should play safely because I'm If I have to win three points, right, but he says play aggressively, you know You might as well give it a shot at this point.

You're already down a lot. So little things like that There's a there's a one of the epigraphs is a not Brad Gilbert, but a different tennis book that that Talks about pushers or dinkers, as they call it in the epigraph. And, uh, it kind of, Connor's tennis strategy has become his life strategy of playing slow and steady and conservatively, not making mistakes.

But that's also the thing that undergoes a transformation over his summer. 

Zibby: Yeah. And yet he ends up the winner, so to speak, maybe, maybe to be determined. Well. I love that. And even how you're quoting David Foster Wallace is in his essays, like bringing them in and Emily's giving him copies of that. That was, that was great.

Yeah. I love, um, tennis and books and I love tennis and I tried to write a novel called 40 love, but it didn't sell, but that's okay. 

Teddy: Was it also a pun on age? Was it 40 years ago? 

Zibby: Yes. I was falling in love again and. 

Teddy: You, if I can turn the tables, you were Married to a former tennis pro, right? 

Zibby: I am. Yes. I know.

I was like, I won't even go there, but yes, I am. I am married to a former tennis pro turned producer. So, um, yes, I think about and I played. I was like you that might like JV tennis team here in New York City. It's like not exactly sweeping the planet. But my husband grew up in Florida, you know, playing at Volataria and Bubba Lopsim.

Teddy: Yes. 

Zibby: That whole, that whole scene. 

Teddy: And he kind of had to, I mean, I think there's a reason the best players are from Florida and California. There's just, they have more access to courts there. They can play all year round. 

Zibby: Yeah, exactly. 

Also, my innate skill would not even be, I mean, if I were to have grown up in Florida.

You know, yeah, but that's funny. So this is going to be a movie. I read that, right? So what is the plan for that? Congratulations. 

Teddy: Thank you. It's in development. I'm, I'm adapting myself for Columbia Pictures and, uh, we are, you know, it's a very slow process. I finished the script or at least so far, but they are trying to get a director now.

And these things take interminably long times to, to come to fruition. 

Zibby: So exciting. Do you have casting preferences? 

Teddy: We have an actor who I can't mention publicly who's on board, but you know, again, these things perhaps it'll drop out, who knows, but we've got someone, yes. 

Zibby: Exciting. I'm picturing, well, maybe not.

I was going to say I'm sort of picturing like a young Topher Grace or somebody like that, you know, but maybe not. 

Teddy: You're not far off physically. They kind of do look alike. Yeah, it's very close. 

Zibby: Okay, good. Excellent. Can you talk a little bit about how you got to this point in your career and like how you became a writer and all of that?

What happened after your tennis career in high school? 

Teddy: My ignominious tennis career came to a close. I've always wanted to be a fiction writer. Um, also wanted to be a screenwriter in college, but fiction was always my, my love and didn't really start taking it seriously until I was about 24. I wrote a, a mediocre novel that did not sell, but fortunately, because.. 

Zibby: Around the same age, how about that?

Teddy: And I'm glad it didn't get published and you don't have to have that caring, toting around with you. 

Zibby: Yes. 

Teddy: But it got me an agent and it got me into graduate school for writing. And then in grad school, I started writing my first novel called Capitoyal. And, and that did sell eventually in my, published in my early 30s and have been writing ever since.

And, you know, that, that doing other things at the time for the first few years of being a copy editor, being a tutor, doing other odd jobs here and there. But now I'm a full time novelist and screenwriter. 

Zibby: So exciting. That's so cool. What are you working on now, aside from the script? Do you have a new novel in the works or no?

Teddy: I am writing a middle grade novel, which is new for me and who knows how it is. I have not really gotten much feedback on it yet, so it could be disastrous, but I'm trying my hand at one. I kind of wanted to write something that my kids could could read. Because they can certainly not read The Winner now and hopefully ever.

Zibby: No, maybe never. 

Teddy: And, um, and, you know, working on more screenplays and starting to adapt other people's work. My wife, uh, her name is Kate Greathead, is also a novelist. Her second book comes out in October. So we're, we sometimes collaborate on, on shorter things. Or we were thinking about collaborating on this middle grade novel, maybe not.

But, uh, there's always various projects in, in the stew. 

Zibby: Let me give you some advice. Not advice, but I have tried to write a middle grade novel recently and took it out on submission with my daughter, who is 10, which I think has a great premise. It's called The Diary Hoffers about a group of girls who can jump back into their mom's diaries.

I don't know. I thought that was good. Yeah, thank you. I think it's really fun. And we did a good job, but the middle grade market is not great, apparently, as people often say, and we are currently now adapting it into a graphic novel. 

Teddy: Interesting. I, I, I, Okay, that's good to know and discouraging to know, but I hope it works out with a graphic novel at least.

Do you know how to draw or do you?

Zibby: No, we hired an illustrator or we are in, I mean, he has started, we have a deal to hire. I mean, I haven't actually paid him or anything. I mean, I will, I promise. That didn't come out right. 

We have, we're in, I don't know, in talks, in contract. Anyway, an illustrator is working on it and we are, but adapting it has been kind of fun because.

It's so much easier, you just need really the dialogue and maybe like one little line for the graphic novel, and my kids are obsessed with graphic novels, so they're like, even if we finish this middle grade novel, we won't want to read it anyway. I'm like, well, I'm only doing it for you, like I don't need to write graphic novels for me, you know, so, so that's actually been quite fun.

But anyway. 

Teddy: And it's fun to adapt your own work into another medium, right? 

Zibby: Yeah, it's a challenge. 

Teddy: It's a challenge, but it's not too challenging, is it? 

Zibby: No, no. Yeah. Yeah. No, that's what I'm saying. It's sort of easier. Like, it's just, you just need the words, like, and they're already there. It's like, yeah, so, um, so that's been kind of fun, but, uh, yeah, I'm sure you'll have much better luck than me with your middle grade, but that was, that's been our, that's been our journey to date.

Teddy: It might be too, too dark, I think, for, for 10 or 11 year olds, but we'll see. 

Zibby: Got it. 


Maybe older middle grade. What advice do you have for aspiring novelists? 

Teddy: Oh boy, I mean, there's plenty of things to say, but I think the obvious one is just to read widely, to read beyond as much as you can beyond your, your instinctive tastes.

I think we all gravitate to certain kinds of books. And while you should get better at writing the, the, or reading the books you want to write, it helps to read and stretch yourself, but ultimately to write the thing that you would want to see in a bookshelf, I think is the best advice to the book that does not exist that only you could write or not to worry about.

market demands or what reviewers would like or even what your, your, your spouse or mom or best friend would like. But what would you like and want to see? And that will always be the best thing you produce. 

Zibby: Amazing. Is there anyone you're embarrassed to, like, show all these sex scenes to or anything? Like, did your mom read it?

Teddy: She has not read it yet. Not really looking forward to her. I've read some racy things in the past that, that I've gotten through. It's sort of like watching, you know, a movie. with your parents and a sex scene comes on. You don't want to be there. But at this age, I'm kind of OK with it. 

Zibby: You're like, I'm a grown up, Zibby.

What are you talking about? 

Teddy: My wife's extended family, when they read it, will be a different matter just because it is a dissection of their culture. I'm certainly not Connor, but I'm closer to Connor than than any other character in the book. And they're closer to the other characters. So we'll see how that goes.

If I could have it. I would want them all not read it, I would want that, but I think they will very much want to read it. 

Zibby: Well, you wouldn't be the first author to sort of blow up their summer community, I feel like. For the sake of a great book. So maybe it all, it all works out in the end. Well, thanks for coming on.

I really, really loved this book. It was just really fun and delicious and just kept turning and I don't know, you did a really good job. It's really good. 

Teddy: Thank you so much, Zibby. 

Zibby: Yeah. Really loved it. All right. Have a great day. 

Teddy: Bye. Take care. 

Zibby: Bye. 

Teddy Wayne, THE WINNER

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