Yankees doomed themselves by not pursuing perfect third base option in 2021

Who's the single most impactful possible free agent the New York Yankees have passed on over the past decade? Not a free agent they pursued and came up short on. A potential All-Star who fit their roster like a glove who they simply ... ignored?

Settling on just one is near impossible. Max Scherzer, available after the 2014 season, would've completely changed their trajectory. Unfortunately, after splurging on Brian McCann/Masahiro Tanaka/Jacoby Ellsbury/Carlos Beltrán, the Yankees had to take their customary year off; it resulted in a postseason miss/deadline sell-off one year later. Bryce Harper's the easy choice. If the Yankees had brought in the Mickey Mantle-idolizing right fielder (turned first baseman!) on a contract that looks like a bigger bargain everyday, after importing Giancarlo Stanton and uncovering Aaron Judge in back-to-back years, they almost certainly have a title by now.

Unfortunately, adding Harper probably means capping themselves and ignoring Gerrit Cole. Unclear what the Harper-Judge-Stanton Yankees' pitching staff looks like. Also unclear if it matters.

For our money, though, the biggest whiff is the pretzel the Yankees talked themselves into when a sequence of generational shortstops were available following the 2021 season. Javier Báez ended up being ... not such a great fit. Carlos Correa? You could see how the Yankees could talk themselves out of the uncomfortable chemistry there. Trevor Story may yet live up to his pedigree in Boston, but he hasn't spent enough time on the field in three seasons to really try. Corey Seager? The only knock on his exceptional left-handed bat was that he might eventually outgrow shortstop and be forced to move to a corner in the latter years of his deal. Wow. What an awful thing that would be for the 2025 Yankees.

Texas Rangers' Corey Seager is Yankees' most obvious free agent miss of the decade

Instead of attempting a splurge, the Yankees put their faith in Anthony Volpe (and, to a lesser extent, Oswald Peraza) to develop into the type of star who eventually becomes worthy of a massive free agent contract. Volpe was a highly pedigreed prospect, but his future position wasn't entirely clear. Did he have the arm strength for short, or would he move to second? Instead of bringing in another talented infielder who could play multiple roles alongside Volpe, the Yankees decided Seager would block him rather than be additive. It wasn't true then. It isn't true now. He was just ... more expensive. That's all.

The Yankees' inaction here has already swung one title (2023), may have swung another (2024), and the rest is still unwritten, as Seager prepares for another season with the newly minted AL West-favorite Rangers. Over the past three years, the 6'4", 215-pound unorthodox shortstop has posted OPS+ marks of 117, 174 and 145. How will he age over the next seven years at $32.5 million per season? He'll probably age perfectly into third base, where he'd give the Yankees a long-term thumper where they're currently considering a platoon.

Hal Steinbrenner, purportedly "out of loot," likely doesn't enjoy the idea of another $32.5 million on the books, but the fans don't enjoy a hole at a premium position, either. The fans should win out. If the Yankees had let DJ LeMahieu walk after 2020 and passed on Carlos Rodón the way they passed on so many other great arms over the past decade, they'd have $40 million of Seager wiggle room and a completed infield picture.

Hindsight is 20/20 on LeMahieu, but it's 2021 on Seager, who everyone knew would be an ideal fit at any position. He just so happened to fit perfectly within the Yankees' uncertainty puzzle, and it's a shame they financially capped themselves too quickly to ever find that out.