Yankees: 3 free agent mistakes NYY cannot make this offseason

Why even write this list? Even if the New York Yankees follow the blueprint 100% properly and do all the homework, you know they’ll end up making free agent mistakes this offseason anyway.

That’s just how it goes! Put any 25 random power hitters and power arms in Red Sox jerseys, and they’ll make a World Series run every four years. Sign the top five free agents on the market and put them in Yankees jerseys, and you’ll uncover foreign substances and aversion to pressure by the end of May. Just keeps happening.

Or, at least, it feels that way most every offseason. That’s why we’re here! To do the best job we can guarding against potential Brian Cashman mistakes before they ever develop.

On the surface, we’re likely all aligned on exactly what the Yankees need to stay away from, on a generic level. Don’t overpay for veteran pitchers past their primes. Don’t overpay for a co-ace for Gerrit Cole when you can trade for a co-ace for Gerrit Cole (and Luis Severino’s returning anyway). Don’t purchase the wrong shortstop … whatever that means to you.

Just because we believe Brian Cashman will be returning for 2021 — with full authority — does not mean he’s absolved from what he wrought on us last offseason.

The Bombers kept telling us they didn’t need to spend for lefty balance bats, only to completely reverse course at the deadline. They also told us they’d done enough to reinforce the bullpen, but ended up scratching and clawing after dealing Adam Ottavino to their chief rivals (Garrett Whitlock might have helped!).

This time around, we’re being promised they’ll blow past the luxury tax threshold after sneaking below last offseason. We’ll believe it when we see it. But if Cashman and Hal Steinbrenner are aligned, the forthcoming spending spree had better look more like 2009 (CC Sabathia, AJ Burnett, Mark Teixeira) than 2014 (Carlos Beltran, Jacoby Ellsbury, Brian McCann, Masahiro Tanaka).

Cashman will be back. He doesn’t get infinite shots to spend like this, though. His rope may seem endless, but it’s safe to say he can’t spit the bit this time around, as the anti-Cash contingent has gotten more impatient in recent years.

3 offseason mistakes the 2021 Yankees can’t make in free agency

3. Paying for Zack Greinke’s (or Clayton Kershaw’s…) Final Years

Of all the things that went wrong in 2021, the pitching wasn’t really the prime offender. In fact, pair Matt Blake’s resurgent staff with the 2019 offense and you probably have a World Series winner with a complete set of nasty changeups to boot.

Now, that being said, we’re not sure there’s a World Series-winning running mate on the current roster. That’s led to the temptation to overpay a pedigreed starter to pair with Gerrit Cole. Presuming Luis Severino is able to return to fire-breathing form as a starting pitcher — quite a presumption! — that could theoretically put the 2022 Yanks over the edge.

Who’s … who’s the guy, though? Banking on Justin Verlander coming off Tommy John surgery (and leaving the Stickiness Brigade in Houston) could be fun, but might not be functional. Max Scherzer? He’s the king of this group, but he seemed disinterested in coming to New York at this year’s deadline.

The biggest mistake, though, would be paying Zack Greinke, who finally appears to have hit a wall as a late-career finesse arm. Greinke no longer lights up the radar gun even to the level of recent years, and has been relegated to playoff part-time duty after a late-season neck injury sent him to the bullpen. The Astros’ “ace” when this season began on a $35 million salary morphed into a soon-to-be-38-year-old back-end innings eater who can occasionally dazzle a lineup, but can’t be counted on to do so. Securing his services for, say, two years at $36 million would seem like a discount, but might not provide much return if Scherzer chooses Hollywood.

And, uh … let’s just throw in a cautionary tag on Clayton Kershaw, too, who might finish his career in Los Angeles but could be tempted with a wad of cash. His season-ending elbow injury is quite worrisome, and there probably isn’t a single prognosticator who thinks he’ll immediately revert to dominance in the terrifying AL East. Another likely no-go here, if the Yankees were even considering it.

2. Andrelton Simmons as Stopgap

So Brian Cashman wants to spend, right? That’s all we’ve heard, yes?

If that mandate somehow remains the same as the big free agents bypass the Yankees for other lengthy pacts (Seager, Correa, Story…), New York’s braintrust had better not wimp out, sell us on Anthony Volpe/Oswald Peraza, and spend their allotted shortstop money on one or two years of someone who can’t hit.

For us, that’s Andrelton Simmons, who’s somehow managed to be both a completely anonymous player as his defensive skills have slipped a notch or two and an agitator, for his publicly anti-vaccination stance.

Once a defensive wizard whose unparalleled magic could carry a sub-100 OPS+ season due to his sheer brilliance in the field, Simmons is now a complete liability at the plate, and the Yankees’ lineup isn’t good enough to accept him as one of their own and shield him. With just two regulars in the everyday order in 2021 who posted above-average offensive marks (Aaron Judge and Giancarlo Stanton, famous guys), the Yanks cannot stomach a Simmons season like last year, featuring a 57 OPS+. He was sub-Ramiro Peña. That’s not papering over any hole for any length of time.

If you believe in the shortstops you have coming in your team’s minor-league pipeline, that’s fantastic. We do, too. But don’t allow that faith to guide you into a patchwork move like Simmons for two years and $16 million, especially since Simmons only creates another problem, and would be less offensively valuable than Tyler Wade.