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The Yankees need to find a way to extend Didi Gregorius

Red Sox shortstop Xander Bogaerts is the latest of many stars who have recently agreed to contract extensions with their clubs.

Only three shortstops in MLB outproduced Didi Gregorius of the New York Yankees from 2017-18.
Only three shortstops in MLB outproduced Didi Gregorius of the New York Yankees from 2017-18.
Photo by Elsa/Getty Images

Yesterday, I wrote about how the recent spate of superstar contract extensions isn’t good for the Yankees. Since the advent of modern-day free agency nearly a half-century ago, the Yankees have enjoyed the luxury of being able to use their considerable financial clout to grab elite talent on the free agent market whenever they chose to do so. That option is vanishing before our eyes, however, as superstars like Mike Trout, Nolan Arenado, Paul Goldschmidt, Chris Sale, Jacob deGrom, and Justin Verlander recently agreed to extensions with their current clubs, rather than test the free agent market.

I also noted that it falls on Yankees General Manager Brian Cashman to work around changes like this in the marketplace. To his credit, Cashman is already on it, having inked both Luis Severino and Aaron Hicks to contract extensions this winter. Early in the offseason, Cash announced his intention to also seek extensions with four-time All-Star Dellin Betances and important team leader Didi Gregorius, both of whom are slated to hit free agency following the 2019 season.

No progress has been reported on either front, and as Gregorius continues his rehab from Tommy John surgery, a new impetus to his extension talks has emerged. The Red Sox just agreed to a contract extension with their shortstop, Xander Bogaerts. The deal guarantees Bogaerts $20 million per year from 2020-25, and also includes a vesting option for the 2026 season. Sir Didi outproduced Bogaerts by eight wins to six from 2017-18.

Just how valuable has Gregorius been to the Yankees? Sir Didi’s 4.2 WAR last season led all Yankees infielders from 2014-18. His 3.7 WAR from the previous year tied Mark Teixeira’s 2015 campaign for second on that list, and Gregorius’ 3.1 WAR in 2015 ranked third. To put his value in further perspective, only 34 position players tallied at least 8.0 WAR from 2017-18. That’s an average of slightly more than one player per MLB team.

Shortstop WAR leaders 2017-18

Player Team WAR FA Year FA Age
Player Team WAR FA Year FA Age
Francisco Lindor CLE 13.4 2022 28
Andrelton Simmons LAA 13.3 2021 31
Trevor Story COL 8.2 2022 29
Didi Gregorius NYY 8.0 2020 29
Carlos Correa HOU 7.9 2022 27
Jean Segura PHI 7.5 2023* 32
Trea Turner WSN 6.7 2023 29
Paul DeJong STL 6.5 2024 30
Elvis Andrus TEX 6.4 2023* 34
Xander Bogaerts BOS 6.0 2026* 34
Corey Seager LAD 6.0 2022 27
Marcus Semien OAK 5.4 2021 30
Stats courtesy of Baseball Reference, table by Brett Borzelli.

Gregorius is clearly the top shortstop slated to hit free agency following the 2019 campaign, so it would behoove the Yankees to do everything in their power to prevent that from happening. Not only that, but considering the unprecedented wave of contract extensions getting tendered to elite talent this year, it wouldn’t be a surprise if Sir Didi ended up being the top free agent at any position next winter.

Given the Yankees’ consistently demonstrated reluctance to seriously pursue top-of-class free agents in recent years, it really could be disastrous if they fail to extend Gregorius during the season, and instead allow the star to hit the open market. I am not optimistic that they would even attempt to win a bidding war for Sir Didi’s services, and there is a steep drop-off in talent among free-agents-to-be after Gregorius at the shortstop position.

Consider the circus that occurred at second base after the Yankees allowed Robinson Cano to leave for Seattle following the 2013 season. Ravaged by injuries and ineffectiveness, the Yankees have had 21 different players slot in at the keystone since. Sure, disappointments like Stephen Drew (-0.4 WAR in 177 games) ultimately paved the way for the arrival of Gleyber Torres. But Torres’ 2.9 WAR during a stellar rookie campaign last year still fell well short of Sir Didi’s production. That’s how valuable Gregorius has been to the Yankees. Extending him now is the Bombers’ best option to prevent that second-base clown show from repeating at shortstop next year.

Some might harbor reservations about this approach in view of Gregorius’ injury status. This risk can’t be ignored, since complications following Tommy John surgery can and do occur. In fact, it happened to the most recent position player to undergo the procedure on his throwing elbow before Gregorius, Mets prospect T.J. Rivera.

After undergoing the procedure in mid-September of 2017, Rivera attempted to begin rehab in Triple-A last July, but was shut down six games later due to arm discomfort. He never returned to action last season, as his elbow still hurt when the minor-league season ended at the beginning of September. During spring training this year, nearly 18 months after his surgery, the young man was still restricted from baseball activities, and the Mets cut him rather than continue waiting for him to heal.

There are far more Tommy John success stories than nightmare scenarios like Rivera’s, though. In Sir Didi’s case, I think it’s a risk worth taking. From 2017-18, only Aaron Judge (13.6 WAR) and Aaron Hicks (8.6 WAR) outperformed him on the Yankees. In franchise history, Gregorius is the only shortstop besides Derek Jeter, Gil McDougald, and Phil Rizzuto to compile 8.0 WAR or more across two consecutive seasons during the Live Ball Era. Rizzuto is in the Hall of Fame, Jeter will be next year, and McDougald was a six-time All-Star.

Gregorius is a special player who has already arrived, he’s proven himself important to the Yankees, and he’s in his prime years of production. Besides, his value — along with the interest level and contract offer he is likely to garner from other teams — will only increase once he does return to action later this season. The Yankees are better off getting a deal done with Gregorius now, rather than waiting.

All stats courtesy of Baseball Reference.