Rethinking fandom with Craig Calcaterra

Fridays in Wrigleyville are made for day baseball. Fans from the North Side of Chicago know that if the Cubs are in town they will play at the Friendly Confines at 1:20. I have sometimes wondered how many people in the sold-out stands fibbed a little to their boss to get the afternoon off, or rearranged their schedule to grab a beer in the sun-drenched bleachers at the corner of Sheffield and Waveland Avenue.

However, the Cubs have another Friday legacy now, what we’ve been calling Blue Friday for the last few months on Cuppa Cubbie Blue. I’m referring to the 2021 trade deadline when Jed Hoyer made what some would call a series of brilliant business decisions to flip a beloved core of aging players for as many prospects as possible and what others might call the day their Cubs fan heart shattered into a million pieces.

Interestingly enough, both of these perspectives can be correct at the same time. We can debate the business acumen of trading a core of players who won a World Series Championship for the Cubs for the first time in 108 years. But what really isn’t up for debate is that all of us are fans. That is true whether you believe Blue Friday was a brilliant strategy to retool an unsuccessful team or whether you believe it was done in accordance with a particularly ruthless set of cost-benefit analyses from Ivy League graduates who fashion themselves as the smartest people in the room.

Craig Calcaterra has covered MLB through many events that were far more consequential in the grand scheme of baseball than last year’s trade deadline. On Sunday, he joined me and Danny Rockett for the latest episode of Cuppa Cubbie Blue to discuss his book “Rethinking Fandom: How to Beat the Sports Industrial Complex at Its Own Game.” This book is a timely look at what it means to be a fan as the people running the nation’s pastime view our loyalty and winning games as just two of many ways they can theoretically profit from owning a MLB team.

I’d encourage you to listen to the whole episode. This was a fascinating conversation that covered everything from how and why owners make the business decisions they make, to why the new CBA won’t fix any of the structural problems with the business of baseball. We explored baseball’s current struggles to attract new fans and its possible future as a second-tier sport.

You will not want to miss how an unlikely game pitched by Greg Maddux changed the trajectory of Calcaterra’s career.

Give the whole episode a listen. Whether you agree or disagree with the thesis of the book, Craig has a knack for explaining complicated issues and he’s a thoughtful conversationalist. I know I’ll be thinking about the issues explored in the book daily as I walk by the Draft King’s sports book construction at the corner of Sheffield and Addison.

“Rethinking Fandom: How to Beat the Sports Industrial Complex at Its Own Game” is available for pre-order now and will be released to the public tomorrow, April 5.