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Today on Pinstripe Alley - 1/20/24

A Saturday with the sports media industry reeling.

SI’’s “Sportsman of The Year 2000” Awards Photo by Arnaldo Magnani/Liaison

I’m going to get a little dour for a moment on this snowy Saturday. Sometimes, friends or family members who know that I edit and write about baseball part-time will conversationally ask if I’d ever like to do it as my regular job. That’s very kind of them, and I will disclose that I’ve been lucky enough to have had opportunities at various points in the past to make it something more serious. Hell, even just running this site as a side hustle is a better chance than more talented folks get.

Sadly, the sports media industry has been trending in the wrong way since roughly around the time I started writing at PSA over a decade ago. Different aspects of the trend have all had their own unique spins to it, but the direction has been the same. We’ve seen major outlets slash their writing departments in recent years, and one of the most devastating blows was struck just yesterday. Sports Illustrated — yes, the same venerable institution that has been in the business since Mickey Mantle was a 22-year-old young buck — is effectively shuttering.

Everyone takes risks at various points of their career. That’s unavoidable. But this isn’t an industry I would want to stake everything on, given what ghouls like the folks who owned SI can do to their staff (and that’s not even getting into the dumb AI stuff). It sucks, but it’s true. So I’m glad to have the part-time, more low-stress work.

Anyway, PSA is not going anywhere, and we rumble on. We’re fortunate to still have a great staff on hand who are willing to devote some of their personal time to this endeavor, so please read and enjoy! Noah will discuss Brian Cashman and lessons in backtracking, Kevin will continue our Top 100 Yankees series with a look back at old friend Jorge Posada, Estevão will consider the Josh Hader Astros signing and the New York bullpen, and Peter will add his own take on Cashman in the year 2024 with a comparison to Bill Belichick.

Questions/Prompts:

1. What is the first Sports Illustrated cover that comes to mind when you think of it?

2. Where does Belichick ultimately end up next NFL season?