No. 27: Chicago White Sox

Thanks to everybody who came out to see me in Florida on Saturday at the Southwest Florida Reading Festival, and on Tuesday night in Boca Raton. Those of you who came out to Boca got a special treat; Chelsea Baker was there! And if you don’t know who Chelsea Baker is, well, I have a great book for you to read.

On the plane now heading for Kansas City, where on Thursday night, I’ll be joined by a cavalcade of stars—Bob Kendrick! Jason Kander! Alex Gordon!—at the Negro Leagues Baseball Museum. I guess it’s sold out, but they’re hoping to open up some space, so you can get on the waiting list here.

And then, Friday-Sunday, I’ll be at the Tucson Festival of Books.

Where is the hope with the Chicago White Sox?

While at the book festival in Fort Myers, I was asked this question by a White Sox fan: Where is the hope?

It’s a poignant question to me, having grown up in Cleveland and having been in Kansas City for so many years when it was my job—quite literally my job, as in I was paid to do this—to find hope in the Royals’ hopelessness. This job required me to take heart in the spring training emergence of Jeremy Affeldt, to find promise in the signing of Emil Brown, to keep believing in the bright futures of Dee Brown and Chris Lubanski and Colt Griffin and Mike Stodolka long after those futures were already sealed.

Rooting for a bad team is one thing. Rooting for a confusingly bad team is another. Right now—with apologies to the Rockies, Nationals, Athletics and, yes, Royals—the White Sox feel like the most confusing bad team going. So it’s not exactly easy to find hope. But let’s go digging for some…

Let’s start in an unusual place: Oct. 29, 2020, the day the Sox hired Tony La Russa.

Actually, no, let’s go back even further, about 20 years back.