Evan Drellich - Winning Fixes Everything

Winning Fixes Everything: How Baseball's Brightest Minds Created Sports' Biggest Mess

by Evan Drellich
Audiobook
Finished: April 17, 2025
Sports Baseball

I remember when I first heard about the Astros cheating scheme. As a baseball fan, I was surprised at how brazen it was. I knew teams would often straddle the line and skirt the rules any way they could to gain an advantage, but didn't expect something so bold and blatantly illegal.

As much as I borrowed this book thinking it would be focused on the cheating scandal, the scandal itself was not a major feature. It was not a disappointment though. The book goes through the early history of Jim Crane’s purchase of the Astros and Jeff Luhnow’s never-ending dive into numbers and analytics building the team and how it rubbed a lot of people around baseball the wrong way sometimes.

The book did a good job going into the conflicts and cut throat culture Jim Crane and Jeff Luhnow cultivated in the Astros organization, all in the name of winning. The culture even went beyond 2017, after they had won the (now tainted) World Series.

This book provided an interesting look inside an MLB club and how a team on the cutting edge of technology and stats tried to find every edge they could think of to win.

It's still disappointing though how many of the organization, both players, management and ownership don't feel like they did anything wrong or that they're "not guilty". I'm sure other teams have crossed lines, and if/when they're caught, they should face punishment as well. But justifying cheating by saying "others do it too!" feels like a cop-out, and it definitely sends the wrong message.