Reel Lives: David Hill On Listening, Writing, Tilting, And Supporting Unions

Every gambler has a story to tell. And so does every person who chooses to make a living in this unique industry.

In our “Reel Lives” series, Casino Reports shines a spotlight on people working in the gaming business, from executives, to analysts, to media members and communications pros, and all points in between.

The subject in this interview: Journalist David Hill, who has written about gambling for such outlets as Rolling Stone, Esquire, The Ringer, and Grantland. He is working on his second book, tentatively titled American Gambler, and in the lead-up to its release, is hosting a podcast called American Gambler Book Club. (Disclosure: That podcast is sponsored by our sister site, InGame.)

Casino Reports (CR): Let’s start with a question spanning the practical and the philosophical. Are you more into covering gambling or gamblers, and why?

David Hill (DH): I’m interested in both. Gambling interests me insofar as I find gambling to be a game. I have a deep interest in games as cultural artifacts and art forms.

Gambling games aren’t always the most interesting types of games, but gamblers are the most interesting types of players because they play for money, which commits them to a more serious and dedicated type of play than simply “fun.” The higher the stakes, the more thoughtful and dynamic the players will be.

I find gambling stories to be the best kinds of stories because they have all the elements great stories need: magic (luck, chance), adventure (risk), and the triumph of the clever over the strong. 

CR: Before your current podcast series, The American Gambler Book Club, you hosted the Gamblers series for The Ringer. Of all the episodes you did there, which one generated the most discussion/feedback/buzz/etc.?

DH: The pilot episode about the casino advantage player Gina Fiore got the most traction by far. After it came out, she was really bombarded with offers to do televison, film, books, etc. There was even a play that was written and staged in London that was essentially a beat-for-beat retelling of the story from the episode, written by someone who never reached out to Gina or myself! 

In the second season, the episode about Rufus Peabody got a lot of attention, too. I think that was because sports betting was still relatively early in its expansion in the United States and there hadn’t been a lot of attention paid to professionals, since the industry has a fairly antagonistic relationship towards pros and they in turn instinctively keep a low profile. So at that time I think that episode was really revealing something new to a lot of new sports bettors who thought the self-promoting touts were the real pros.

CR: As someone who lives in New York, do you care particularly which bids get the casino licenses? Do you expect to hit up the new casinos much?

DH: I only care that the jobs created are union jobs. Currently the unions are backing the Hard Rock site near Citi Field, so I suppose that’s the one I’m supporting, too. 

I’m sure I’ll go to the casino, but they better have 3:2 on blackjack.

CR: Ever gone on tilt as a gambler, and if so, what’s your worst tilt story?

DH: I’ve gone on tilt plenty of times. One of the earliest stories I have of going on tilt was one of my first trips to Las Vegas in my early 20s. I played poker, mostly low stakes limit hold’em, like $3-$6 or $4-$8, at casinos all over town — pretty much anywhere with a poker room, which wasn’t that many properties back then. I ended up winning a real bundle, like over $1,500. I also collected a dollar chip from every casino I visited to bring back home with me as souvenirs. At that point, I was duty bound to go to the Mirage and play the highest stakes I could afford with my winnings. I played $15-$30 and lost every dollar I had. I ended up walking all over Las Vegas to cash in all the dollar chips to have enough money for food.

CR: Of all the things happening in the world of U.S. gambling in 2025, what do you think 2018, pre-fall-of-PASPA David Hill would have been most surprised by?

DH: I don’t think I could have predicted much of anything that is happening right now! But honestly I think the thing I’d be the most blown away by is the success of Circa in downtown Las Vegas. Just seems something like that in 2017 would have felt impossible to imagine — a major luxury resort in downtown Las Vegas that features a sportsbook as its main attraction. 

CR: Tell me one skill or lesson from your previous career as a union organizer that you apply to your work as a journalist.

DH: I think listening to people tell me their life stories was the most instructive experience I had as an organizer that helped me as a journalist. I traveled to every corner of America and talked to people from every walk of life, listened to them tell me all about their lives and their experiences. I learned a lot about how to tell stories, about what kinds of things actually motivate and matter to people, and mostly how to listen to people rather than just wait for my own turn to talk. Good writing in the world of journalism and nonfiction is actually pretty easy, because the people you’re writing about will tell you all the details you need to make the story work. If they don’t, then you aren’t asking enough questions, or you’re asking the wrong kinds of questions, or you weren’t listening when they told you. 

Reel fast!

The best slice of pizza in New York can be found at …

Pizzeria Suprema.

All-time favorite book, either fiction or non-fiction, non-gambling division?

Flannery O’Connor — A Good Man is Hard to Find.

I know you’re not a lifelong New Yorker, but you’re a longtime New Yorker and a Knicks fan. What are your baseball, football, and hockey teams of choice? (Besides “whoever I have money on.”)

Mets, Falcons, and Devils.

I’ve seen you sometimes with a mustache, sometimes without. Is your wife pro or anti the ‘stache?

Strongly opposed.

I learned from your LinkedIn that you were once a writer for sketch comedy group UCB. What’s your favorite sketch show (not counting SNL if the answer is SNL because that’s too easy)?

I Think You Should Leave.

What Halloween candy are you most likely to steal from your kids after they bring home a big haul?

Airheads.

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You can keep up with David via his Substack, X, BlueSky, or LinkedIn, or just seek him out in the near future at one of the downstate New York casinos, provided the blackjack odds are reasonable.

Previous installments of Reel Lives:

Mindway AI CEO Rasmus Kjaergaard On RG, AI, And Bruce Springsteen

UNLV International Gaming Institute’s Dr. Kasra Ghaharian On AI Impact

PR Man Adam Rosenberg On Sports Betting, Social Media, And The Freelance Hustle

Kelly Kehn On Entrepreneurship, The Value Of Diversity, Paying It Forward, And Broadway