“An important part of being a columnist is failing every once in a while or somewhat on the regular. You write the bad ones so you can write the good ones.” Wall Street Journal sports columnist Jason Gay talks with Zibby about his career trajectory leading to the WSJ, becoming a character in his readers’ lives, and, of course, Tom Brady. They also cover the art of reading print, and the emotional recent loss of Jason’s friend and fellow writer, Tom Perrotta.


Zibby Owens: Welcome, Jason. Thank you so much for coming on “Moms Don’t Have Time to Read Books.”

Jason Gay: I’m so grateful for the invitation and thrilled to get your invitation a few weeks ago and honored to be here.

Zibby: I have to say, you are a personal favorite of my husband’s and mine. He is a sports nut and former professional tennis guy and sports all the time. In fact, these used to be books on top of me, as I showed you my office. They used to be football helmets, which I also made him bring somewhere else. We read your column all the time. I often read it out loud to him. That’s one of our rituals. He was so excited I was talking to you today.

Jason: Wow, I’m deeply honored. Where are the football helmets? Did you give them away? Are they in a basement somewhere?

Zibby: No, no, no, I did not give them — they’re downstairs. They’re in his little nook of football-watching heaven.

Jason: I think you’ve upgraded a little bit from the helmets. It looks pretty good to me.

Zibby: I think so. Thank you.

Jason: I’m very flattered by the joint reading. I hear that once in a while. Honestly, that’s the best thing I can possibly hear. I’m very flattered.

Zibby: Now this is just sounding creepy of me. Two years ago or so, I was reading Little Victories. I downloaded the audio of it also so that he could listen to it. We listened to you on this, not cross-country, but we were driving from Arizona to LA. We put you on to listen to you for a while. Then after a while, he’s like, “I don’t know. I kind of like you reading him better.” I was like, okay.

Jason: I don’t have a great voice for radio. I don’t have that kind of stentorian gravel that you want for real gravitas in audiobooks. I tried my hardest. I don’t blame him if he prefers your voice to mine.

Zibby: I hope he would prefer me to you. I am married to the guy, so you know, nothing personal.

Jason: Absolutely.

Zibby: I guess I’m in trouble if he starts really strongly preferring other audiobooks. It’s a warning sign for me.

Jason: My column at The Journal, more recently they’ve started putting an audio component on it. It’s a computerized voice. It’s not a human voice, but it sounds quite human-ish. It’s at the top of the column. It takes some getting used to. I want to do it myself. I’d love to read it myself, but maybe people would prefer the computer. I don’t know. It’s interesting because they tell me that there’s a type of reader who is very interested in getting their news information that way. Listen, I’m in favor of any application that can make people pick up a newspaper in any format. I support it.

Zibby: I would vote for your voice over a computer voice. I’m sure my husband would agree. Although, I have to say, I actually read a newspaper in my hand, a hard copy. I think I’m one of the last people. Maybe you do too. You write for a newspaper. How do you read it?

Jason: I’m embarrassed to say that — I shouldn’t say embarrassed to say, but I am much more of a digital reader than I certainly was five, six years ago. I do believe very strongly in the print product and the kind of news consumer that reads the print product because I think that — I think studies bear this out. I don’t want to say you’re a more informed consumer, but you’re reading things that you wouldn’t necessarily read digitally. What a digital product does is it starts to learn you, Zibby. It starts to figure out what you like to read and then starts to, the same way that your Spotify feed does or anything else does, your Instagram feed, it figures out things that you are interested in and your preferences. Whereas when you read a print product, everyone’s getting the same thing. It’s not specific to you. Your eye might be drawn to stories that you wouldn’t otherwise be handed by an algorithm. That’s the formative newspaper-reading experience of my childhood, which was opening up the paper to read the thing that I wanted to read. Then my eye would travel to something else. I’d read that. I’d read that. Pretty soon, you realized you read three or four stories that you wouldn’t otherwise be reading. I think that’s a really valuable thing. I would hate to see a moment when there wasn’t that option for readers.

Zibby: I agree. I also feel like you can read so much more. I know they say that digital reading saves time, but I can go through a whole paper in the — you can skim as you flip the pages and get information that would take so many click-throughs. I think it actually saves time.

Jason: There’s just something also about the art of reading print. You’re a New Yorker, I believe. You’re somebody who knows how to read a broadsheet newspaper when you have a person on your right and a person on your left. You fold it carefully.

Zibby: I am not good at that.

Jason: Oh, you’re not good at that?

Zibby: No, I am not good at that.

Jason: There’s still time.

Zibby: I’ve tried. I’m more like, spread it out on my kitchen island. Sometimes I end up with four days at once. Then I just go through the whole stack.

Jason: I’m the same way. I have young children in my house, which means oftentimes when I spread out newspaper around the house, pretty soon someone’s doing fingerpainting on top of it. That is a hazard.

Zibby: Yes, that is an occupational hazard. Sometimes I even read them at night. It’s how I relax type of thing. I feel like I should talk to you about the Super Bowl, not that I actually really like football that much, but it is the day after the Super Bowl. I read your column this morning about Tom Brady who you keep writing about a lot, the absurdity of his —

Jason: — You can’t avoid him. I can’t shake him, Zibby. He’s in my blood.

Zibby: I know. I feel like you have a thing with him. You just can’t believe it. Is it just that a man about your age is actually doing this thing? What is it? Is it a personal thing or what?

Jason: Of course. He’s mocking me. He’s forty-three years old. He should’ve been falling asleep at halftime at the Super Bowl yesterday, not playing in it, not winning the Super Bowl MVP. Yet he’s out there competing still at the pinnacle of the sport. That Super Bowl yesterday, that was the seventh ring. The next closest person has five. He’s in a class all to himself. The fact that he is at forty-three and shows no signs of stopping, is making no indications that this is going to be it for him, said the other day before the game that he’s open to the idea of going past the age of forty-five, that’s real rare air. There is an NFL player who played until age forty-eight, George Blanda, but he was a kicker for the latter half of his career. That Tom Brady is doing this at such a critical position, at a vulnerable position — everyone’s trying to get the quarterback. It’s just remarkable. Listen, I have Brady fatigue like I think a lot of people do at this point, but I also have a real sense of wonderment for what he’s accomplished because we literally have not seen it in the history of this sport.

Zibby: By the way, I think the way you feel about Tom Brady this year is how the rest of us women might have felt about J.Lo at the halftime show last year. It’s like, really? This is on the table as something that we could be doing?

Jason: As an impossible standard.

Zibby: Yes, setting an impossible standard that just makes the rest of us feel bad.

Jason: It doesn’t take much to be an impossible standard for me. I think someone who can just walk ten thousand steps a day is already in rare air, to me. I’m struggling with the base minimums. I can see that, for sure.

Zibby: Ten thousand is a lot of steps. That’s so many steps.

Jason: I guess that is.

Zibby: Who made that rule? I don’t know.

Jason: The big ten thousand society.

Zibby: Exactly. More shaming for those of us who maybe get two blocks to the park with the dog and that’s about it. Not that that would be me, of course. I’m getting twenty thousand steps a day. All those coffee trips.

Jason: Is it going to be one of those things like with how they always keep changing the health standards? You can eat this. You can’t eat this. They’re going to come back, actually, you only need fourteen steps. Ten thousand, we were wrong all this time. Fourteen steps, that’s it. That’s all it takes. Maybe they’ll do that, Zibby.

Zibby: Maybe it’s like how doctors say “do this twice a day” because they know you’re only going to do it once a day. The recommendation is ten thousand because they know there’s no chance. If it’s ten thousand, then maybe people will get to two thousand.

Jason: I am sure there is something to that, absolutely.

Zibby: Aspirational guidelines. To make this more of a sad conversation, your essay about your friend Tom Perrotta — I hope I pronounced that right — was so sad and beautiful. Then I went and read his essay and everything too. Maybe you could talk for a second about your relationship with him and even how COVID gave him those extra moments and everything.

Jason: Thank you for asking about him. I love talking about my friend Tom. He shares a name with a very distinguished novelist, Tom Perrotta, but this was a different one. He wrote for The Wall Street Journal for about ten years. I knew him the whole time. He was our tennis writer. He was the guy we sent to Wimbledon and the French Open and had this really wonderful job and was an incredible writer but then was stricken with brain cancer about four years ago and battled it very, very hard. He outlived all the predictions of how long he would go. We lost him in early January. Before he died, in the fall, The Journal published this essay by Tom that talked about the last ten months or so of the pandemic and how amid what had been, obviously, an incredibly disruptive and challenging situation for so many people, he found this incredible silver lining of family and the fact that family had to be home with him. This was a part of his life that he hadn’t really experienced professionally because he was always traveling around. He was always on a plane somewhere. He had missed things. Here was this time in his life when he knew he didn’t have a lot of time left. He was getting every maximal moment with his children, his wife, his close circle. It was just a very fascinating perspective on this.

This period of time has been so rich with lessons of perspectives and context. I’ll be the first to say, boy, I feel like the luckiest person around, the fact that my family has been healthy and the fact that I’ve been able to work through this. I know many people are facing far greater and severe challenges than I could ever imagine. I felt that what Tom wrote was beautiful. I know from talking to him it was something he really wanted to say. I feel like those of us — you’re probably one, Zibby. At some point in life you encounter people who know they don’t have a lot of time left. There’s this version of it, the movie version of great clarity that people — they know what they want to do. They’re going to do this last thing. It’s this trajectory. It’s not like that. He was angry. He was mad about things. He just felt he was getting a raw deal. He died at forty-four. That is young. He also really felt things. He knew that what he was getting in these months, he really needed it and he felt was going to be incredibly valuable to his children, too, as they got older and they knew that they had had this time with him. He was a magical guy. We miss him a great deal. He was a huge contributor to the newspaper. I was really struck by the readers who responded, other writers, people in the tennis community, athletes, players who really liked the guy, who were moved by him. We’re all still processing a little bit even though we had time to prepare for this outcome. My thoughts are primarily with his wife and children, of course. I think that people have done right by him. I think that he will be remembered as a true gent and a true, wonderful writer.

Zibby: Do you feel like losing him or having to watch this and the anger at the life not lived, does it make you feel different approaching your day-to-day life?

Jason: Absolutely. Yeah, sure. How can you not? I had an experience with Tom where — he was the person, of course, we sent to these big tournaments. He was the top dog. As he started to have the health issues, it was harder for him to do every part of it. He was the person who could do everything. Then as time went on, he needed some supplementation. I went with him to Wimbledon one year and was writing some stuff on deadline about Federer and Djokovic. He was sitting with me. He was like, “I just wish I could still do that.” By that, I meant literally just physically, mechanically do it really quickly on deadline and write like that. That was something that was harder for him. He needed a little bit more runway to get stuff going. You don’t spend any time in the orbit of somebody who is facing something like that and not have it change you and not have it give you a major, necessary dose of perspective, and all those things I need all the time, I think all of us need. Again, the best part of it was the fact that he was able to have that time with family and friends toward the end.

Zibby: I’m sorry for your loss. It is always a good reminder even though — they say it’s a gift when you realize. It’s a not gift. It’s still terrible. Still would prefer it not to ever happen, but I guess if there’s anything…

Jason: Of course. Since this is about writing, there is something magical about the fact that people live on through their writing. If you’ve not read any of his work, it’s not terribly hard to find. Type in his name, Tom Perrotta, Wall Street Journal. You’ll find avalanches of great stuff that he did over the years. I think that that will be a real comfort to his family, his children, but also to the many people who knew him and loved him. There is something wonderful about the fact that that outlives us all.

Zibby: Maybe you should compile his essays into a book and write a forward for him.

Jason: We are underway. We’re underway with all these kinds of thing.

Zibby: I have no new ideas. It’s fine.

Jason: It’s because we want his kids to have — his children, sadly, are quite young still. They’re probably not reading The Wall Street Journal, but we want them to have that because it is a remarkable legacy of work.

Zibby: Speaking more about writing, how did you end up as the sports columnist for The Wall Street Journal? How did that happen?

Jason: They threw a bunch of applications up in the air and mine was the — I’ll tell you what happened.

Zibby: When did you start? Go back. Go back in time.

Jason: I’ll tell you what happened. I had kicked around newspapers and magazines for quite a number of years. I had mostly recently, at that time, been working at GQ magazine, which was a magazine I had been at for quite a while. I got a call from a friend of mine who The Journal had called first and said, “Hey, The Wall Street Journal’s looking for a sportswriter. Would you ever do this?” I was like, “What? The Journal? What?” I was not a Wall Street Journal reader. That’ll not shock anyone who reads me. I don’t really fit the profile of someone who’s financially literate or newspaper-literate in any sort of traditional sense. It was still a cool-sounding job, so I went in there and I talked to them. We did this thing where it was basically a tryout. You write columns based on things that were happening, but they don’t go in the newspaper. They just want to see if you can put the verbs after the nouns and spell things correctly and you can write on a deadline, that kind of stuff, things that were important to them. I did this audition over a few weeks. Then they said, “Okay, we’ll try this part time.”

That was about ten years ago. Then it became full time a little while after that. I have to say, it’s the best job I’ve ever had by a landslide. I’ve had some nice jobs and great bosses and great publications to work for, but there’s nothing like working for a paper or any kind of publication where the audience is massive. The Journal goes out to three million-plus a day. Whether they like you or they don’t like you, you’re going to hear from them. You’re going to hear from readers. I just never had had that kind of feedback and relationship with readers before. It’s something I still treasure, the fact that you’re in people’s lives. You described your experience and sharing with your husband or reading in print. If you’re around enough, and my column gets in the paper a few times a week, you start to become a character in reader’s lives for better or for worse. Not everyone likes you. I just consider that an incredible honor and privilege to be able to have that role. That’s my story. Everyone comes to the paper a little differently. I didn’t really fit the standard profile of somebody who arrives at The Journal. Most of the people are much smarter, much.

Zibby: Yours is, by far, my favorite column. I think part of the reason why is that you put so much of yourself in everything. Not a lot of the other columns in The Journal tend to do that. There’s fantastic other things as well, but it’s you. It’s what on your mind that week and stuff with your kids. Yet you have this funny way of spinning everything. Putting the Olympics in your mom’s living room, I would never have thought to write that essay. That’s just funny. It’s a different way of seeing the world. Yet you get to know you as well. It’s very cool. It’s like going to stand-up show or something.

Jason: Yes, I am a failed comedian. I am just working it out in The Wall Street Journal. Everything you say is so kind. I appreciate it a great deal. I’m only doing what I know how to do. I’m not somebody who is going to be able to write some sort of constantly serious, stern proclamation about the world a couple times a week in the newspaper. I try to keep it light because that’s just who I am. One of the many good pieces of advice I got very early on is be true to yourself. That will be your North Star. If you are true to yourself, you’ll never get tangled because you’re taking a take because you think that’s what people want to hear or you’re being something you think that’s what’s going to get the most clicks. For better and for worse, you are yourself. As far as putting my own self into columns and things like that, that was a challenge, first of all. There’s typically institutional resistance to that kind of thing wherever you work. It’s not so much just a Journal thing. I was very lucky to have publishers, editors who were willing to let me try that, experiment with it, fail with it quite often, still. I think that’s an important part of being a columnist, is failing every once in a while or somewhat on the regular. You write the bad ones so you can write the good ones. I think that, again, ultimately what you’re hoping for is a relationship with the reader to keep you on track. Every once in a while, I hear really great, nice things from people. Then I hear every once in a while from people who are like, you got that one wrong. Enough is enough with that. That relationship and that kind of feedback is essential to what I’m doing. This is a long-winded way of saying that this is the only skill I have, Zibby. If this doesn’t work out, I’m going to be selling hand puppets somewhere. This is all I have.

Zibby: It seems to be going well so far. This is it, Zibby. This is all I have, is my thrice-weekly column in The Wall Street Journal. I’m such a failure in life. Feel sorry for me.

Jason: You talk to writers all the time. I think that there’s a kind of writer who sort of has a master plan or a worldview about the way that they want to do things and have a prescription for writing. This is how it should be done. This is how I do it. I don’t feel that way at all. I feel like we’re all kind of figuring out as we go along. While in newspapers there are some things that are hard and fast, like I need to be rigorous with fairness, be truthful, to have integrity — those are unbreakable rules. I think the rest of it is open for discussion in terms of style and approach. In terms of there being rules for the way to write, I would guarantee you that most of the writers that all of us really love in some way or another were rule breakers and did it a little differently and changed norms and were confrontational and broke away from the pack. None of which is to say I’m doing any of that on a regular basis. I feel like writers have more liberty to experiment and do things differently. I wouldn’t, certainly, be prescriptive to people and say there’s only way to do this because there’s not. There’s a great many sportswriters that I love, love, love who — humor’s not their thing. They’re not trying to be funny. They probably look at me and think I’m some sort of goofball. I think there’s room for all of it. Sports is a topic that has such a wide range of fans, people who are utterly casual who are watching the Super Bowl as their first football game of the season or the decade sometimes. Then there are people who are feeling every minute of every game and are obsessed and want a different kind of product. I think there’s room for all of it.

Zibby: I don’t think any writer really feels confident ever. I’ve talked to a lot of people. I think even the most accomplished, brilliant literary icons are like, ooh, I hope my next books works. Seriously.

Jason: I’m sure you’re right. I think that there’s a kind of person who is very capable of faking it, at least just in terms of their confidence and project a kind of surety that I just don’t have, but I think you’re right. Ultimately, you drill down and we’re all kind of squishy in the middle. I’m sure that’s true.

Zibby: Your book, Little Victories, was fantastic, but it was a while ago now. Are you thinking of writing another one or what?

Jason: We are on the verge of some excitement here, Zibby. There is a project in the works that I’m super excited about I’ve spent quite a while working on. I can’t launch into details yet, but I’m really excited to get it out into this planet. It has been a while. I loved doing Little Victories. I love the fact that I hear from people all the time, still, about reading it. It’s been a minute. I’m really excited about what’s coming.

Zibby: Please send me an early copy of whatever it turns out to be.

Jason: I’m just going to read it into the phone, just audiobook . How’s that sound?

Zibby: Perfect. Then I can just read it back to you.

Jason: You’re like, hard pass. Can I have the computer voice please? Thank you.

Zibby: You just gave so much advice, but one last piece of advice for people listening. Do you have one last parting piece of advice that everyone out there who’s an aspiring author should know, or aspiring writer or columnist?

Jason: Oh, gosh. This is just my experience, but I think one of the great superpowers of writing is humility. By that, I mean the ability to recognize that you don’t have the answers always. You get it wrong sometimes. You can think out loud. I think that we are in a moment, because of the way social media works and what it prioritizes and what gets attention, that being incredibly declarative to the point of coarseness and rudeness and awfulness, that’s what clicks with people. X is X. Y is Y. Z is Z. A is A. Life isn’t like that. There are no clear-cut answers. There are clear-cut truth, but there aren’t necessarily clear-cut answers to the big questions. I think it’s okay for people who are even in the opinion business to be sorting it out. I don’t know the answers to this question. I have a little bit of, I see this and I see that. It doesn’t necessarily track with social media and the way that people react to information now, but I think it’s human. I think it’s real. I think there’s a whole subcurrent of readers who appreciate that kind of candor.

That’s a piece of advice that works for someone who’s writing opinion columns about sports or someone’s writing opinion columns about stuff that’s far more serious than sports. It applies to people who are writing fiction and nonfiction. You can work it out. Show your work. As they say in the math, show the work. That’s certainly been my experience. This is an old cliché, but the longer you go, the more you realize you don’t know. That can be a real asset. To bring it all back to Tom Brady and the Super Bowl, here he is. He’s standing on that stage Sunday night. It had been nineteen years since the first one. You look at somebody who is still approaching his sport with this curiosity about it. What’s it going to be like next year? I still like this. I’m still getting something out of it. I haven’t done it all. I think that kind of thing is a real vital thing no matter what you do. That’s sort of vague advice, but I’m sticking to it, Zibby.

Zibby: It works. I’ll take it. Jason, thank you. My husband is also quite funny, I have to say, and loves sports. I think we should all go get a drink or something at some point.

Jason: Can I interview you for one quick second? I appreciate that. What’s the tennis here? What’s the tennis background?

Zibby: He taught professional tennis. He played junior tennis in Florida, went to , and then taught for ten to twelve years and now is a movie producer.

Jason: Is he still out there hacking away?

Zibby: He plays for fun.

Jason: Not for money anymore.

Zibby: Not for money, no. He’s like my on-staff pro.

Jason: It’s good to have an on-staff pro. How is his second serve these days?

Zibby: We don’t actually do serves.

Jason: That’s fine.

Zibby: We just hit, but his serve is pretty good.

Jason: My father coached high school tennis in Cambridge, Massachusetts, for forty years. He was an obsessive city tennis player. He liked the crazy chain-link tennis, the cracks in the court. The nets were crooked. That was his game. He liked the city game. His question to ask to people was, how is your second serve? I think the great Harry Hopman said you’re only as good as your second serve. I always thought that was the knowing tennis question to ask.

Zibby: My second serve is horrific, so that doesn’t speak well about my tennis.

Jason: My second serve looks like someone lightly tapping a butterfly into a butterfly net. It’s so weak. You would be embarrassed. You would be embarrassed not just for me, but for the entire sport of tennis.

Zibby: Awesome. Thank you so much. Thanks for spending the time with me.

Jason: What a great time. Say hi to your husband for me. Say hi to the family. I really appreciate it. Let’s do this again sometime.

Zibby: I would love it. Take care. Have a great day. Enjoy the coffee.

Jason: Bye, Zibby. Thank you.

Zibby: Bye.


Little Victories by Jason Gay

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