brian cashman yankees
Kim Klement | USA TODAY Sports

Dear Brian Cashman,

He’s finally done it. The thing we never imagined would ever happen post-Steroid Era, even on the Yankees. As YES announcer Michael Kay once said about Derek Jeter’s 3,000th hit, Wednesday’s 8-3 win over Toronto was history with an exclamation point.

In case it wasn’t obvious, I’m talking about Aaron Judge hitting his 61st home run of the season. Not just any season, though. After the last out of the World Series, the likely AL MVP, one Aaron James Judge, will be a free agent.

If you’re not sweating, you should be. That cookie-cutter $230 million deal you offered prior to Opening Day? Forget it. in fact, it’d be more profitable to make actual cookies with the offer and have a charity bake sale outside of Yankee Stadium. As of right now, you’re staring down the barrel of a $300 million offer. Minimum.

But don’t worry, Cash. This isn’t your first rodeo. You don’t spend 25 years in the general manager’s chair without getting your hands dirty in free agency talks. In fact, you almost seem to thrive on them.

Who can forget the 1998 offseason, fresh off a World Series and record-setting year? Bernie Williams won the AL batting title in his contract year and almost signed with the hated Red Sox! Yet, you and the late George Steinbrenner pulled through and upped the offer accordingly.

Or how about after the 2013 season? Fan favorite Robinson Cano wanted that 10-year deal, you held firm at seven with options. Cue the Seattle Mariners making a $240 million mistake. Sure, the fans were upset at first, but we got over it. It took us a couple of years to realize it, but you were right to let him go.

But what about now? Aaron Judge wants and deserves his money. It doesn’t matter if this historic season is a one-off. Judge is an elite player who deserves a significant contract. That doesn’t mean a record-breaking deal by any stretch, especially with him already 30 years old. Still, $230 million just won’t do.

Because here’s the thing, Brian. If Judge leaves in free agency, he won’t be the main villain in the story. No, sir. That would be you. Want to know why? Well, to be perfectly frank, the fans are getting a little tired of you and your “analytics” obsession.

Who spurns bigger names that fill an immediate need for value that works, but isn’t quite the same? That would be you. Who clings to minor league prospects that can be traded for a big fish, only to develop them to death and they don’t really leave their mark? You. Who faces questions from the media about some of his more questionable moves and doubles down again and again and again?

If you’re not seeing a pattern here, sir, then you’re missing the point.

Carlos Correa was probably the most exciting shortstop on the market last offseason and signed a short-term deal with the Twins. Even with some timely hits, is Isiah Kiner-Falefa really a better option?

On the minor league side, Estevan Florial and Clarke Schmidt were once top prospects. Now, Schmidt’s been streaky as a reliever/sometimes starter and Florial has no clear future with the team. Not to mention, the young outfielder hasn’t particularly impressed, hitting .185 in a handful of MLB appearances.

But it’s all OK, right? Because the great Brian Cashman and his analytics team have all the answers. If Aaron Judge leaves for another team, the numbers have a good reason and Cashman will not be challenged. Trust his vision, for he knows all, right?


Here’s a quick reminder, Brian. When Judge hits free agency this winter, there’s no guarantee you’ll be the one negotiating. Your contract is also up at the end of the year and, if we’re being honest, Hal Steinbrenner will probably keep you around. This season has been successful enough that you and the analytics team will live to fight on another five-year deal.

Except you know better than anyone that success does not equal security. Just ask Joe Girardi, who had the Yankees one win away from the AL Pennant in 2017 before not getting a new contract. Regardless of where the Yankees finish in the playoffs, Steinbrenner can easily do the same thing to you.

Which is why, right now, I’d like to remind you of your most infamous free agency negotiation yet. Remember when Derek Jeter, the Captain himself, hit the market after 2010? Yeah, those contract talks got real nasty, cutthroat even for you. Your relationship with him, the most legendary Yankee of the last 30 years, is still strained to this day.

And let’s not forget Jeter’s recent speech at Yankee Stadium. His saying the fans would see more of him has everyone speculating. He’s no longer a part-owner of the Miami Marlins. Though unlikely, it’s fun to think about the potential of, I don’t know, president of baseball operations Derek Jeter. He’d sooner move the Yankees to New Jersey than let Aaron Judge leave.

That puts you behind the eight-ball, Brian Cashman. If you get a new contract, it’s because Hal Steinbrenner trusts you to re-sign Aaron Judge and make him a Yankee for life. The Yankees can already outbid any team, will be in a decent position to up their original offer, and you know it.

The fans on #YankeesTwitter complain about you every time something goes south. This is your opportunity to get back in the fans’ good graces regardless of any other moves. Forget about the lack of World Series rings. Keeping Aaron Judge after a highly-anticipated free agency would make you a bona fide New York hero. Do not screw this up.

And if Judge walks? Well, you’d better have Juan Soto waiting in the wings down the road.

Your move, sir.


Josh Benjamin (on behalf of all Yankees fans)

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Josh Benjamin has been a staff writer at ESNY since 2018. He has had opinions about everything, especially the Yankees and Knicks. He co-hosts the “Bleacher Creatures” podcast and is always looking for new pieces of sports history to uncover, usually with a Yankee Tavern chicken parm sub in hand.