Recently, a young man from Chicago’s South Side went viral for his feelings about what happens if, or when, his White Sox lose. The sixth grader spoke straight from my soul when he said he would have “no heart for baseball” if the Sox lose. This has long been my relationship with baseball and the Yankees.
Frankly, when it comes to Major League Baseball, if it is not the Yankees, I have no desire to watch. Never have, never will. Call me an old-timer, but I would rather read about the outcome the next
morning than try to enjoy another team winning in the moment. Unfortunately, like so many other times over the last 17 years, that means that after enjoying the fall weather until darkness forces me inside, I now have no baseball to enjoy.
This year, with a lockout looming and the longest championship drought of my fandom’s life, the darkness feels earlier than ever. The void that the NFL and betting app commercials are trying their best to fill still feels empty. I have never done a good job of preventing the Yankees’ elimination from souring me on sports for a bit, but this year, I have decided to try an unexpected way to fill the void.
If you did not know, Mike Pinsky is on Season 51 of Survivor. Why would a random man on a reality television show that has been running for over 26 years matter in this context? Well, you see, Pinsky just so happens to be the Yankees’ assistant director of baseball operations.
What is an assistant director of baseball operations? According to what has been released and what Pinsky himself has said on the show, his role involves advising general manager Brian Cashman on roster construction, assisting with contract negotiations, and helping evaluate trade and free-agent targets.
So essentially, Pinsky gets paid to do what we all do right here on our beloved Pinstripe Alley, but with a direct line to Cashman. In an interview with The Athletic, Cashman offered the kind of praise he might give to any player in the Yankees organization, calling Pinsky a gifted person and saying he believes Pinsky has what it takes to endure and win. Gotta love that Cashman just recycled the lines he has used to describe players year after year.
For those who are not familiar, Survivor is a game played on an island in Fiji that combines physical competitions and social manipulation to whittle a group of contestants down to a “Sole Survivor.” The show has really changed from a survival-like competition into something more like a chess match involving immunity idols, advantages, twists, and jury management. That means backstabbing or building relationships so well that people still vote for you to win at the end.
Now, this show is not for everyone, but it does offer a chance to quickly strip away some layers and learn a lot about the players. The show is designed to make contestants uncomfortable and expose their generosity, arrogance, paranoia, patience, and resilience in a foodless vacuum.
The season’s fourth episode airs tonight, and spoiler alert: Pinsky, unlike the Yankees, is still alive. Our very own Mr. October. I am officially locking in, not necessarily because I think this somehow counts as a Yankees win if he pulls it off, but because I want to learn all I can. I want to know what Pinsky will do. How will he handle things? When is he going to reference work and apply it to the strategy of the game he is playing? Will he say the word “analytics”?
I mean, come on, what if he tells us how much the Yankees really depend on analytics in their decision-making? Pinsky has said there are parallels between the Yankees’ management structure and his experience playing Survivor. A fellow contestant compared playing with Pinsky to playing with a sponge, saying he spent his time soaking up information without giving anything back. Call me a sponge too, because whether it is fair, foul, or fruitless, I want to learn more about one of the personalities in the Yankees’ front office and its processes while hopefully being entertained once a week.
Realistically, I know we will not get Pinsky telling Jeff Probst about the Yankees’ salary restrictions or potential free agent targets. I also realize this sounds like a fan who is so starved for actual team success that they have been reduced to cheering for a front-office suit eating bugs on an island just to feel something in October.
But hey, here’s to hoping other fans enjoy watching whichever team wins the World Series. For me, I’ll support the last Yankee standing. I hope Pinsky has the time of his life and represents the organization well. At the end of the day, this is his individual journey and story, but it’s kind of cool to have a Yankee still alive in October, at least for now.













