Gerrit Cole or Didi Gregorius: Which would you rather have on the Yankees next season?
That shouldn’t be an either/or situation; The Yankees can afford both. However, it’s not hard to envision the Bombers choosing to upgrade pitching this winter at the expense of their shortstop of the last half-decade.
Gregorius has been an integral part of the Yankees’ turnaround. He stabilized shortstop after Derek Jeter retired. He turned into a power-hitting machine from the left side. Perhaps most important, he’s helped make the Bronx Bombers fun. You don’t put a price tag on that last part, yet one can’t help but mention it.
But he may not get to see the Yankees’ current run through to the end, to no fault of his own.
Gregorius, after all, is a free agent after the season. He’ll be 30-years-old on Opening Day 2020 and is making $11.75 million this season with a raise presumably coming on a multi-year contract.
Though next year’s free-agent market has a handful of quality third basemen, headlined by Anthony Rendon, Gregorius should be the top shortstop. As of now, the only other top shortstop set to hit free agency in the next two years is Andrelton Simmons. Gregorius has the all-around skills and personality to thrive anywhere.
It’s reasonable for Gregorius to expect much more compensation than the top corner infielders on last year’s market — Eduardo Escobar and DJ LeMahieu, each of whom received less than $25 million on their contract. Free agency is broken and unpredictable, but even with a qualifying offer, he should command 3+ years at north of $13 million annually. Perhaps much more than that, though who knows with the current climate for free agents?
This wouldn’t be a problem except the Yankees play with a budget. A self-imposed one, and one that allows plenty of room for profit, but a budget nonetheless. When thinking about the Yankees’ free-agent plans, you have to keep in mind the top luxury tax tier, which will be $248 million in 2020.
The Yankees have something around $230 million on the payroll this season with CC Sabathia, Brett Gardner, Dellin Betances, Austin Romine and Gregorius coming off the books after the season. That accounts for around $36.3 million. Aroldis Chapman could opt out, but the Yankees would then have another hole in the bullpen.
At first glance, it’s easy enough for the Yankees to re-sign or replace all of those players and stay under the tax. They have a ready-made replacement for Gardner in the organization. However, as anyone who watched the last 10 days of Yankees pitching noticed, they could use another starter (or three), preferably high-quality ones.
Gerrit Cole and Hyun-Jin Ryu headline a robust starting pitcher market (compared to last season) with Madison Bumgarner, Jake Odorizzi, Zack Wheeler, Cole Hamels and Rich Hill set to join them. Stephen Strasburg could be another high-profile starter out there if he opts out.
If the Yankees want to play in the Cole-Strasburg-Bumgarner free agent market, they’d begin to start bumping up against the competitive balance tax. Cole, who will be 29 next season, could command $200 million and over $30 million annually. Strasburg, 31, would take a similar per-season commitment. Even if the Bombers choose to go for lower-profile starters, they’ll still have to pay out a significant sum over Sabathia’s bargain deal.
Let’s say you get Cole for $25-30 million a season. That bumps the Yankees payroll to around $220 million, give or take. If they want to re-sign Betances or another reliever — far from a given if Chapman is retained — he would add another $9-10 million. This is before you lock in a backup catcher, fourth outfielder, extra starting pitcher or Gregorius, and leave room for call-ups and trade deadline upgrades. They’ll also need to hand out raises in arbitration to Aaron Judge and Gary Sanchez, which further adds to their payroll.
So a big starting pitcher may limit the Yankees the room to sign Gregorius under the top luxury tax tier. That would be crushing to fans and perhaps to the team as well, though there is a successor waiting in-house: Gleyber Torres. The Yankees could shift Torres to short, allow LeMahieu to man second base and give third base to Gio Urshela, Miguel Andujar or a cheap, veteran alternative. (They could also eschew a pitching upgrade and sign Rendon, though that doesn’t make as much sense over keeping Gregorius).
This would be a short-term decision with LeMahieu becoming a free agent in the 2020-2021 offseason, but it’s a potential solution to the Yankees’ luxury tax questions in 2020. Torres can fill shortstop long-term, but he’s talented enough to play second base as well. Perhaps they view Thairo Estrada on next season’s roster.
Gregorius still fits the roster, contrasting with the Yankees’ glut of right-handed power bats. Furthermore, the Yankees’ infield depth this season served them well as injuries overtook other parts of their roster. Losing Didi’s bat, plus his clubhouse presence, would be a blow.
Of course, the Yankees could find other ways to shed salary. They could try and trade Jacoby Ellsbury’s $22.1 million contract for a larger overall deal that comes with a lower luxury tax cost. This is a method perfected by the Dodgers (see: Kemp, Matt) in recent seasons as they flirted with exceeding the luxury tax. They could also extend Aroldis Chapman at a lower AAV.
I don’t mean to sound alarm bells as this is both far too early and maybe not even something the Yankees consider. They know Didi is valuable and fits in New York. However, this isn’t completely bizarre and worth some light-hearted speculation in the interim.
The Yankees can both sign top free agent pitchers and retain Gregorius, or they can simply extend Didi and find cheaper alternatives on the pitching side. His presence has been invaluable to the Yankees, and keeping him should be one of their top priorities this fall. Still, with the team’s budget and questions around the roster, the front office could view him as expendable.