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What happens when Moneyball author tackles travel softball?
Book Review: Playing to Win by Michael Lewis
From the author of Moneyball, The Big Short, and The Blind Side, here’s a much lesser-known audio-only tale of big-time youth sports.
If you're deep into the world of travel softball, Playing to Win by Michael Lewis is a must-listen that will hit close to home. Lewis, a master storyteller, dives into the whirlwind journey of competitive youth sports, with a particular focus on the intense environment of girls' softball. What starts as a simple, local league experience quickly escalates into a full-blown commitment that many families will recognize—the endless tournaments, the miles traveled, and the hefty price tags.
Lewis doesn’t just tell his story; he taps into the broader experience that so many of us share—investing time, money, and emotions into our kids' athletic dreams. He pulls back the curtain on what he calls the “youth sports industrial complex,” shining a light on the massive business machine that thrives on our passion for the game. But don’t worry, this isn’t some outsider criticizing our way of life. Instead, Lewis offers a thoughtful reflection on what it all means—for us, our kids, and the sport we love.
The short audiobook balances humor and insight, making it both entertaining and thought-provoking. Lewis challenges us to think about what we're really aiming for—whether it's a college scholarship, a shot at the pros, or just the sheer joy of the game. He doesn’t shy away from tough questions, but he handles them with the care of someone who’s been in the trenches just like the rest of us.
For those who are all-in on travel softball, Playing to Win is more than just a listen—it’s a chance to reflect on the journey we're all on. It’s a reminder that while the pursuit of victory is exhilarating, it’s the lessons learned and the memories made along the way that truly count. Lewis gets it, and he’ll make you see the game—and your role in it—in a new light.
So, if you’re ready to look at the big picture and maybe even see your own experience in a new way, give Playing to Win a listen. It’s the perfect companion for those long drives to the next tournament.

image by muzzyco from Getty Images
You’ll have to hear Lewis explain it himself. But you’ll be glad you did.
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P.S. Some of you will be able to listen to this book entirely during a single ride to a tournament. And it has a happy ending despite some cynical takes along the way. Unfortunately, the real-life “epilogue” to Lewis’ softball journey was tragic. Choose your own adventure. Google or don’t. Parental Guidance is recommended. But the book itself is too rare of a specimen for softball families to ignore.
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