A Q&A with Daniel Barbarisi on leaving newspapers, writing his first book and diving into the world of daily fantasy sports

Every week we will run a Q&A with a wonderful reporter to talk about what’s right and wrong with journalism, their interests and random other stuff. Some are friends. Some are just people whose work we really respect. Some cover sports. Some don’t. Hopefully all will be interesting.

This week, it’s with Daniel Barbarisi, a longtime baseball writer, a former colleague of Jared’s at The Wall Street Journal and now a published author. Dan’s first book “Dueling with Kings” just came out, so we thought this was a perfect time to have him as a guest. (We already had his wife, Amalie Benjamin, so it’s only fair.) Here, we discuss Dan’s career to this point and talk in-depth about why he decided to leave the newspaper world, how he decided to pursue this project and what writing a book is really like. 

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The questions are in bold. The answers are not.

  1. We start all our Q&As in the same way–at the beginning. So: How did you break into journalism, and what led you to where you are now?

I remember the first time I saw my name in a real, live, non-school newspaper. It was the local Westmore News, and they paid me $40 to cover mundane school board and town council meetings in my minuscule hometown of Rye Brook, N.Y. I was around 16 at the time, say 1995, and it completely blew my mind that someone would pay me actual hard currency for going to something and writing what I saw. It was intoxicating. I’ve always loved telling stories, and always loved being someone who could tell other people what was going on. Being a journalist was really the only thing I’d ever wanted to be, as far back as I can remember. I just never fully believed it would happen, because to me, going from writing local stuff for a tiny local paper to actually getting a job at a major metro daily seemed like going from the Earth to the moon. But I got a few breaks, most notably when the excellent Neil Swidey helped me to land a good internship at the Boston Globe when I was at Tufts University. One thing led to another, and soon I was covering crime and Politics at the Providence Journal. My favorite assignment there was spending a few years as the Providence City Hall reporter; I felt like I was part of the fabric of the city.

Then, one day in 2008, I was in Florida for my grandfather’s funeral. And I got a call from one of the editors, who told me, “When you come back, we want you to cover the Red Sox.” They were in the playoffs at the time, and I figured they needed an extra hand. That sounded like fun, even though I don’t think I’d written a sports story since high school, and even then only a couple. So I asked if I’d be helping out for a week or so. And he said, “No, you’re going to be a full-time beat writer now. It’ll be fine. You’ll figure it out.”

Gulp.

But I guess I did figure it out, because a couple years later, the WSJ called and asked me to cover the Yankees for them, and so I moved over there at the end of 2010, and did the Yanks for five seasons, before leaving to do the book full time. Segue please….

2. You just published your first book! It’s called Dueling with Kings, and it’s a deep dive into the strange and sordid world of daily fantasy sports. What about that topic made you think it was worth dedicating the time and effort into to write as a book? What made you want to pursue the story?

I first encountered the daily fantasy phenomenon in the spring of 2015. At the time, it blew my mind that this existed at all — it sure seemed like a form of nationalized, legalized sports betting to me — and even more so, it shocked me that seemingly nobody was talking about it. The game was fun, there was an insane amount of money flowing into it, and there were small problems wherever I looked, thanks to the Wild West nature of the industry at the time. I was certain it was going to explode before long — the one thing, in this process, that I really got right — and that pretty soon, everyone everywhere would be talking about it. So I decided to get inside it early, trying to be there for when the inevitable tumult did happen. I just feel like it’s so rare to find a story that’s big and has so many tentacles — money, drama, spectacular growth, characters, legal intrigue, potential cheating — but where nobody is really talking about it in more than a surface-level sense. I think if you’re lucky enough to encounter one of those, a huge tale waiting to be told sitting in plain sight, you gotta grab it and ride it wherever it goes. That’s what I tried to do here, as terrifying as that was.

3. We’ll get back to the book in a second, but before that, I’m curious about your situation leading up to writing it: You had a pretty sweet job covering the Yankees for The Wall Street Journal. Plenty of great journalists would give a lot to be in that position. Yet, you decided to leave that gig to pursue the book. So… why? How did you know this was the right moment to take the plunge? How much did you worry about the risks involved — financially, professionally, etc.?

I believed in the story completely, and I believed I had gotten myself in a position to tell it, and that the chance to do something potentially transcendent like that is worth the inevitable and painful costs. Believe me, I didn’t do so lightly, and if there was a way to get a book leave, for instance, and be able to keep my job long-term, I would have taken it. But such is life. There were also logistical factors at play. At the time, because of the job, I was living in New York, and my wife, Amalie Benjamin, was living in Boston. So something had to give. Doing the book allowed me to solve that life issue in the short-and-long term, though it obviously introduced a series of other problems, like, um, what I do next now that the book is out. Anybody got any ideas…?

  1. Now, back to Dueling with Kings: What were some of the challenges you faced while going through the process? What surprised you? How much did the seemingly unending cycle of litigation against FanDuel and DraftKings impact your process?

The process itself was the challenge. So, to explain, in the book, I try to tell the story of the origins, growth, rise-fall-rise again of daily fantasy sports, explaining just what the heck this thing is and where it came from and what the heck happened with it when the world of DraftKings and FanDuel went from nobodies to the biggest advertisers in America to scandal-plagued companies and then to the targets of a sprawling legal battle. But I actually thought the best way to tell that story was from the inside, trying to see if I could make the journey from money-losing “fish” to fearsome “shark,” which is why I quit my job to see if I could make it as a professional DFS player — a similar style to books like Neil Strauss’s The Game or James McManus’s Positively Fifth Street.

From an book-writing perspective, I did that for two reasons. First, I didn’t want to write a straight business book. The compelling stuff about this world is what happens deep inside it, the personalities, the characters, the drama, and not just how much money the companies raised and how they squandered it trying to kill each other. That’s the skeleton of the book, the framework, the larger story I am trying to tell, but I believed that I could bring that story to life if I made it human at the ground level, not the $3 billion sky-high perspective.

Second, I couldn’t really wait to see how it turned out and then write from the back. It would take too long, in my mind, and the industry was so darn chaotic that I couldn’t predict where it would go. But if I could live inside it and tell the story of everything that happened around me, it would enable me to create a compelling narrative that helped the reader to understand that world no matter where it ended up — and also, would let me write and create mid-stream, allowing the production process to happen so, so much faster.

This basically worked out just the way I’d hoped. But it was incredibly stressful, because I’d be writing as it all unfolded, and then some huge thing would change — the New York attorney general shutting the companies down in New York, for example, or later, the companies deciding to merge — and that would invalidate some of my reporting, and enhance other parts. So it required an insane amount of shifting on the fly, whacking things that were so good but suddenly weren’t relevant or vice versa as the ground shifted underfoot seemingly every other week. The most terrifying part was after I could no longer make changes; if something dramatic happened between then and publication, around 4 months, I couldn’t account for it at all, and it might make half of what I wrote instantly outdated. Fortunately, things stayed calm, finally, long enough for me to get to publication day unscathed.

5. Hopefully this isn’t stealing from the book at all, but you’re more than just a daily fantasy sports writer — you also got pretty good at them! What sort of credibility with sources did that give you, since you weren’t a schlub like most of us who get hosed on these platforms? Also, why “pimpbotlove?”

Well, I only got good about 7/10 of the way through the book. For most of it, I’m a schlub trying not to get hosed too badly. And not a terribly successful one. But yes, I did eventually get pretty good. Once I did, that afforded me a certain level of cred in that world, but almost every single relationship I’d made and needed for the book was built long before that. That said, most of those people seemed genuinely happy to see me succeed, like they’d played a role in creating me… which, in many cases, they did.

Pimpbotlove is explained in chapter 12… so you’ll just have to read the book to see!

6. At which part of the book process did you lose more sleep: Reporting it or writing it? Having gone through it once, what do you think you learned from the experience that you would do differently when and if you decide to write a second book?

I was doing both at the same time, so it was kinda one process. But basically, the writing part was really, really fun. Since I’m a character in it, and my opinions and thoughts and comic asides are part of the story, it was a completely different experience to write this than anything I’ve done before. I’d never done anything, ever, that wasn’t straight, dry newspaper style, and I’d very, very, very rarely included myself in the story. I’ve never wanted to be a columnist, never done creative writing. So this was a departure, but honestly, it was a blast.

But that definitely took some adjustments, and that’s what I understand better now and for any future works: It took a dramatically different method, for me, to write this book than in what I did writing a newspaper story.

For 15-plus years at newspapers, the idea was to report, report, report, and then vomit everything out onto the page around 4-7 p.m., hammer it into something usable, hope it’s good, make a few tweaks, and then send it out into the world. Then forget it ever happened and move on to the next thing. I thought that’s what this would be like, too, just in a longer-term way. I was totally wrong.

When I tried to write this the way I’d written newspaper stories — without a ton of forethought or planning as to more than just what the lede might be and what information I needed to impart — I failed miserably. Everything came out flat, dead. I realized, slowly, that I needed to put much, much more planning into each section, and I began diagramming out each paragraph in my head long before I’d actually write anything. Then, once I had about 2-3,000 words-ish written in my head, knowing how one idea would flow to the next, what the transition would be, what the next thing I wanted to communicate was, etc. etc., I would finally go write. That would sometimes mean days without writing anything at all. But when I did, it all came gushing out and was far more effective.

7. What do you see as the future for you? You’ve been a politics reporter, a sports reporter and now an author. Do you think of yourself as a full-time author now? What would it take to get you back into the newspaper/short-form journalism world?

I just like having new challenges, new adventures and getting to feel like I’m using my brain in new and different ways. This has certainly been that. I’m certainly trying to give it a go as a real author now, but a lot of that will depend on what the next project turns out to be. But I never say no to at least exploring an interesting possibility, in whatever discipline.

8. What, if anything, do you miss about covering baseball every day? It’s not the easiest lifestyle, but it is a lot of fun. What was that first spring training like, to see the Yankees report to Tampa, and you’re not there?

I miss the other writers, getting to be a part of that rambling, traveling beat crew. That was a heckuva lot of fun, and some really great people were on there during the times I was on the Yankees and Red Sox beats. I actually didn’t mind the travel itself. Someone was paying me to see the country, and that was wonderful. Sure, there was work all afternoon and night, but that left mornings mostly free to run along the rivers of Chicago, go to museums in Kansas City (the very underrated WWI museum is awesome!) climb the hills of San Francisco… what an opportunity. The baseball part? Well, that happens every year, whether I’m there or not. I don’t think about it a ton.


9. We usually ask our guests here what they would change about the sport they cover. But you’re not covering a specific sport, so let’s try this: What about the book process would you change if you could? I’ve never written a book but have seen a little bit of the process, dealing with agents, writing the proposal. What could be improved if you could change anything? (Yes, we know this will give you cover to praise your agent and publisher first)

Woo… lemme see, I’m still just a first-timer, so really, what do I know? But I can definitely say that I was a little surprised as to how little control the author has at points in the process. Maybe that’s not the case for Michael Lewis, but for me, it definitely felt like I was along for the ride at various points, which was quite interesting.

10. You shared a story a few years ago about an episode in which you tweeted about Hannah Davis — then Derek Jeter’s girlfriend, now his wife, and an SI swimsuit model throughout. You got caught major flak from Jeter over it. You recounted the story here, so I’m not asking for a rehash, but what did that teach you about the privacy of athletes and celebrities and how reporters should go about reporting/tweeting/blogging/Snapchatting about them? How did it change your thought process about what is and isn’t for public consumption?

Sometimes we forget the platform we have. I think — I certainly thought at the time, at least — that my random musings did not matter a whit to someone like Derek Jeter. Why should he or his care what I say? But with the diffusion of voices now, I think it actually matters less who is saying it and simply that it is being said. Certainly in that period, 2013-ish, the line between what it was okay for writers to talk about on Twitter and what wasn’t was still in flux — it still is today, of course, but back then it was even blurrier. It’s funny, because I’m generally not someone who is particularly Twitter-active, or funny, or looking to use it as that kind of platform. It was more just, “Huh, this is a funny tidbit/observation.” But sometimes, the famous people who exist apart from us actually exist a little closer than we think after all. I do wonder if it would have elicited the same response from him in the world of 2017. I guess I’ll have to try again and find out.

BONUS: Hey, we really appreciate you doing this Q&A, and we hope your book does well. Want to give our readers a reason they should go buy this mighty tome?

It’s funny. I wrote this book to tell the story of this crazy world for non-daily fantasy players. That was the whole point, to explain that world for people who WEREN’T part of it but who saw those commercials, paid a little attention to the scandals and wondered what the heck happened there. I was trying to tell the definitive story for those people. But many seem to think this book is FOR daily fantasy players. I’m glad they’re liking it and thinking it’s authentic, but I was trying to tell their story to the larger world, not write a tale for them. So, I’d say, if you have ever had a fantasy team of any kind and ever wondered what all that fuss was about, what was really going on inside those companies, whether the whole thing was good or bad or criminal or screwed up or fun or if you just wanted to read a really, really crazy yarn, then this is the book for you. No need to have ever played a second of daily fantasy to enjoy it.

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