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Is it time for the Yankees to extend Didi Gregorius?

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Once the tax consequences dissipate, there is no excuse not to extend Sir Didi.

American League Championship Series Game Six: New York Yankees v. Houston Astros

If one player were to embody the upward-trending Yankees of the past two years, Didi Gregorius is the one. Not only was he the best trade acquisition in recent memory, but he also provided some of the best moments in recent Yankees memory, both with his three-run home run in the wild card game, and his two home runs in Game Five of the ALDS.

The first time I wrote about Gregorius was way back in March of 2014, and largely because his profile fit the Yankees perfectly. Derek Jeter was on his way out, the Diamondbacks had their very own Chris Owings, and it was low-reward enough that the Yankees would not have to sacrifice much.

Yet even based on my hopes, Gregorius has exceeded them wildly. By total value, it’s exactly what you want to see from a young player:

Not only that, but his underlying stats are even more encouraging. Combined with the juiced ball, cutting down on his strikeout rate, and pulling the ball in the air more often, he has sent his home run number from just nine home runs in 2015 to 25 home runs last year:

What has separated him from his predecessor isn’t necessarily his bat, which is coming around but will never touch the consistency of Jeter, but his glove, as he is easily one of the better defensive shortstops in the league. Even though the defensive metrics are split on his nominal value (11 Runs Above Average by FanGraphs, 4.9 FRAA, and 1 DRS in 2017), the eye test tells the whole story; Gregorius has great range, and one of the best arms of anyone at the position.

This is a long way of saying that Gregorius is currently one of the most important players on the roster, and one of the most important players on the team moving forward. Despite the fact the Yankees also have Gleyber Torres, Miguel Andujar and Thairo Estrada in the wings infield depth-wise, Gregorius was a four-win player last year. That’s what you hope one of those players is.

That begs the question: do you extend Gregorius? The reason for waiting past this offseason makes some sense given the looming luxary tax. If an extension were to be signed today, the average annual value would be calculated into the tax, possibly giving the Yankees less financial flexibility with the same salary paid in 2018.

Any reason for not extending him once this year has concluded, considering the tax issues will be gone, would be... insufficient. The Yankees have said in the past that extensions are not their modus operandi, other than the first Robinson Cano deal, but it would really behoove them to lock him up now. He’s a fan favorite, incredibly valuable in the prime of his career, and he has already shown a knack for coming up in big spots.

To guesstimate, let’s say that he puts up three wins in 2018. Assuming a peak of age 29 and a decline of a half-win a year, he would be worth about 10 wins through 2023. Assuming a $12 million payout in his final arbitration year, and $10 million a win in free agency, it would warrant something like a five-year, $82 million contract. If he has a great year this year, you could bump that up to $90 million, or more. You could even argue that number factoring in inflation. Once again, I’m using back-of-the-napkin math here.

If we’re using that really, really rough estimate, it makes an extension make a ton of sense. Gregorius has marketability, with defense that should be serviceable into his mid-30’s, and there’s always that chance that he really is a true-talent four-win player now that he’s tapped into that power potential.

It all depends on this year, and going against the Yankees’ usual tendencies to extend players, but signing a fan favorite shortstop seems like a no-brainer move. Long story short: give Sir Didi his money.