Yankees should move quickly to buy low on Didi Gregorius

The Yankees have a lot of work to do in free agency, but now would be a great time for Brian Cashman to lock up Didi Gregorius for the long haul.

Didi Gregorius isn’t going to be ready for the Yankees on Opening Day, but he’s clearly a part of the organization’s long-term plans. The talented shortstop also happens to be in the last year of his current contract. That makes it a great time for Brian Cashman to approach him about a long-term extension.

The idea of signing an injured player to what would need to be a big-money extension might seem rather dangerous at first. However, the more we think about Gregorius’ situation with the Yankees it might be a genius move for the front office.

While there is some risk of Tommy John surgery damaging Gregorius’ throwing ability, the success rate for the procedure is much higher now than it used to be when it killed careers. If pitchers can come back stronger after having the surgery performed on their elbow, there’s no reason to think that a shortstop can’t achieve the same effect.

That means the Yankees can reasonably project Gregorius to come back this season as roughly the same player they saw in 2018. He’s only 28-years-old so he’s not likely to experience age-related regression in the immediate future.

The player Gregorius should be is one of the best shortstops in the game. He was the eighth-best shortstop in all of baseball last season in terms of WAR with a total of 4.2. Gregorius probably won’t hold that value throughout all of his next contract but he should easily remain an above average player at one of the game’s most important positions.

The good news for Yankees fans is that Cashman and the organization are already considering entering into negotiations with Gregorius. Despite his elbow injury, they remain committed to keeping him as a long-term piece of the team’s core.

When you feel that way about a 28-year-old entering the last season of his contract it’s definitely time to talk about an extension. That’s precisely what the Yankees should be doing with Gregorius this winter.

It does not, however, mean they should hand him a full-fledged market deal. Instead, they should try to take advantage of the uncertainty surrounding his injury. In essence, the Yankees should try to sign Gregorius to a slightly below market deal.

The reason Gregorius might accept such a contract is that it offers him security. While the success rate for Tommy John surgery is quite high, there’s always a possibility he might not respond positively to the procedure. Even if his recovery takes longer than expected it could really hurt his market leverage next winter. The idea of exchanging a few million dollars over the course of the deal for some immediate security might be appealing to the talented shortstop.

Cashman isn’t going to be able to secure a massive discount here. A good comparison for the deal Gregorius might be looking for is the contract the Mariners provided Juan Segura. He’s making an average of $14 million per season on a five-year deal. For the record, he is the same age as Gregorius and the two players were only separated by a WAR of .1 last year.

A good deal for the Yankees would come in slightly below that contract. Offering Gregorius a five-year deal with an average annual value of $12 million per season could be a win for both the player and the organization.

There’s no guarantee Gregorius and his representatives would bite on this sort of deal, but it’s the exact kind of move Cashman should be looking to make at this time of year. Securing Gregorius on a below-market deal would give the Yankees additional financial flexibility in the future. That could allow the team to add another impact free agent before the 2019 season begins.