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Baseball College

The Application

You have just finished your three hundred page autobiography. Please submit page 217.”

My actual submission is lost to time, but I remember well how I answered it. The admissions application for the University of Pennsylvania used to include some unique questions, and that was one of them. I remember pouring hours into getting it just right, trying to figure out some future reason why I’d be writing my autobiography and then placing a key episode deep in the second half of it.

I imagined myself as the general manager of a Major League Baseball team that had just won a World Series, and I was doing what winners often do — publish a book to tell how they did it. For one page anyway, I was the architect of a champion, the builder of a great roster that won it all.

A job in baseball eluded me, and I was a generation too early for the new wave of smart, young Ivy Leaguers who did deep dives in analytics and found their way into every front office in a matter of a few years. GMs used to move up through the ranks, former players, coaches, scouts, and managers who climbed through front offices. 

I sent a resume to the Dodgers once, but a career in baseball never seemed genuinely possible. The highlight of my baseball playing days was winning the Most Improved award at a baseball summer camp when I was 9 or 10. Of course, to be Most Improved it helps if you weren’t very good to start with.

Turns out there are many other ways to win a championship. Or 10 or 20 or more. You just don’t get parades. Or champagne baths. Or book deals.

By Jason Winston

Jason Winston is a lifelong baseball fan and player of various simulation games. He has worked as (among other things) a professional educator, journalist, marketing writer, and compliance analyst. He has managed tens of thousands more games than Connie Mack did, and with a better winning percentage, too!

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