3 Yankees offseason missed connections that sting the most

We know what you’re thinking: how can you possibly narrow down this list to only three players the Yankees missed out on this offseason?!

Thanks for asking. Here’s how we’ve chosen to handle wrapping up the 2021-22 Interest Kings’ offseason. If a player was never a realistic target, but you wanted him anyway, he’s not here. If a player seemed like a nice fit, but it eventually required an outlandish commitment to secure them (or, at least, outlandish in Yankee terms like Trevor Story’s deal in Boston), they’re out. If the player went all offseason long without being on the Yankees’ radar — even in price-gouging terms — we’re not covering them.

If you thought the Yankees might sign Kyle Schwarber, God bless you, but no.

This list is reserved for the three most perfectly-attainable fits the Yankees decided to shirk for whatever reason, even as the players fell into their self-imposed price range.

Two of these players you’ve undoubtedly thought about a ton in recent weeks. One? Not so much, but that’s why we’re here. We want to take you into the wayback machine all the way to the start of the winter. We want you to snap out of the sunshine and make you miserable all over again.

Hey, not our fault! You clicked! Why’d you do that?

Honorable mentions on this list go to:

• Joc Pederson, who’s been a perfect Yankees fit last offseason, last summer, and again this offseason, but unfortunately ended up out of their market when he signed for the hefty price of Dead and Co. tickets
• Carlos Rodón, the risky left-hander who was so risky that arguably the smartest front office in baseball signed him
• Justin Verlander, the one who got away twice (and why’d the Yankees go for him this offseason, exactly?)
• Corey Seager, the third baseman of the future?
• Marcus Semien, the second baseman of the future?
• Matt Olson, someone we’d have surrendered Oswald Peraza for … but who apparently cost more
• And Max Scherzer, who unfortunately had no interest in coming to New York — I’m sorry, what was that?

All due respect to those seven whiffs and the other 99, but this trio will hurt the 2022 Yankees the most.

3 free agency near-misses that hurt the 2022 Yankees the most

3. Freddie Freeman

Any time you learn that six years and $162 million — with $57 million worth of deferrals — is too rich for the Yankees’ blood, it’s time to locate the nearest defibrillator.

Of course, missing on Freddie Freeman is tough to assess. In all likelihood, he was always split between the Atlanta Braves and Los Angeles Dodgers, and the reported emotional conversations he had with his father ahead of bolting the ATL seem to suggest that’s accurate.

So we’re inclined to take Freeman off this list … except … in the reporting that followed his choice, all indications were the Yankees had less than zero interest in adding another nine-figure, long-term deal to their docket before extending Aaron Judge. So the Yankees never had any intention of figuring out just how much money might sway Freeman in his darkest hour after the Olson trade.

All that Buster Olney-driven speculation about whether the Yanks would “jump the market” on Freeman? Turns out they had a shot to try, but never had any intention of doing so! All the late-moving momentum that indicated New York was ahead of the Dodgers? Might’ve been! But they passed!

Losing Freeman hurts, but learning through the Freeman non-move that the Yankees are going to try to extend Aaron Judge and sit tight otherwise hurt the most.

2. Jacob Stallings

The New York Yankees had every intention of upgrading their defense at catcher this offseason, it seems.

Even though they pretended, back in November, that they were perfectly set to move forward with Gary Sánchez. One more year! One more year! One more year!

So, here we are. New York wanted a defensive upgrade, but they’re left with Ben Rortvedt, his career .169 average, and his sore oblique, while the Miami Marlins get to move forward with Jacob Stallings.

The Red Sox pursued Stallings, then backed off. The Pirates had Stallings, and all the Yankees do is make trades with the Pirates. That’s, like, their whole thing! And yet. And yet!!

Stallings, 32 years old, was worth 3.0 WAR in 374 at-bats in 2021. He’s far from a superstar, and isn’t someone who is a mortal lock to catch 130 games on a World Series contender. But he’s got a Gold Glove and a better pedigree than Rortvedt — and, again, plenty of people were chasing him.

How much did the deal cost? Just two top-30 Marlins prospects in Connor Scott and Kyle Nicolas, as well as right-hander Zach Thompson. Didn’t the Yankees have a bunch of 40-man guys they had to get rid of this winter? Again, we’re just connecting dots.

Apparently, though, the Yankees were too set on Sánchez to go for Stallings … until they traded Sánchez and obtained someone who might someday grow up to be Stallings. Doesn’t a Stallings/Higashioka platoon sound more appealing than what we’re about to wade into?

Unfortunately, Derek Jeter sniped Brian Cashman here, and the two catchers passed like ships in the night.