Should the Yankees look to extend Didi Gregorius?

On Friday afternoon, the Yankees agreed to terms with most of their arbitration-eligible players. One of the notable contracts belongs to shortstop Didi Gregorius, who signed a one-year, $5.1 million deal. A Super Two player, Gregorius remains arbitration eligible through the 2019 season. Does it make sense for the Yankees to try to extend their shortstop?

Gregorius received a $2.675 million raise this offseason. This makes sense considering he’s coming off of his best season to date. In 2016, he posted a .276/.304/.447 batting line with 20 home runs across 153 games. This represents a trend of improvement dating back to his time in Arizona.

He managed a 75 wRC+ with the Diamondbacks in 2014. Following the trade, that jumped to an 89 wRC+ in 2015, and 98 wRC+ in 2016. He’s improved across every aspect of his offensive game, with a notable leap forward in the power department. His 20 home runs in 2016 more than doubled his previous single season best.

As Gregorius prepares to enter his age-27 season, it’s reasonable to expect this improvement to continue. He’s on the precipice of the peak batting years. He’s demonstrated that he can make adjustments and take steps forward at the plate. The Yankees could have themselves a very good hitting shortstop. They could also have an expensive one, as quality hitting pays in the arbitration process.

With that in mind, it makes sense for the Yankees to touch base with Gregorius regarding an extension. The discussion then shifts to what sort of a deal could we expect between the two sides. The recent noteworthy shortstop extensions could provide a framework for a potential contract.

Early in the 2015 offseason, the San Fransisco Giants signed Brandon Crawford to a six-year, $75 million deal. This covered his final two arbitration eligible seasons, as well as four years of free agency. The other extension came in February 2014, as the Braves inked Andrelton Simmons to a seven-year, $58 million contract. The deal spanned Simmons’ entire arbitration eligibility as well as a single year of free agency.

Here’s how each faired in the season leading up to the extensions. Gregorius’ 2016 campaign will serve as a reference point.

Based on these comparisons, it’s tough to see a perfect fit. The Crawford deal covers several years of free agency while the Simmons extension replaced his entire arbitration eligibility. It’s far more likely that Gregorius will seek a shorter contract in order to test free agency. He will also likely command less money than Crawford, who emerged as one of the National League’s top hitting shortstops in 2015.

While its tough to project hypothetical contracts, there’s one that sticks out, a 4-year deal worth $52 million. Does that sound familiar? If it does that’s because it’s the Patented Yankees Batting Contract™. Jorge Posada, Johnny Damon, Hideki Matsui, Brett Gardner, and Chase Headley all agreed to those deals either as free agents or extensions. The Yankees must have a stack of those contracts pre-printed.

If signed today on top of his current contract, this would cover his two remaining arbitration eligible years as well as two seasons of free agency. It would represent a significant pay raise for Gregorius while also allowing him to try the open market prior to his age-31 season. That’s not a bad deal.

On the Yankees end, this would add some cost-certainty to the mix. It would also allow them to take their time developing top prospects Gleyber Torres and Jorge Mateo. If one of those two force the issue, the hypothetical Gregorius extension wouldn’t be so cumbersome that it would prevent a trade. This principle holds true if Gregorius’ production falls off a cliff. It wouldn’t prevent the Yankees from playing Torres or Mateo in his place.

The Yankees have been more amenable to contract extensions in recent years. They successfully extended Robinson Cano and Brett Gardner, and attempted to extend Russell Martin and Aroldis Chapman. As a young, up-the-middle player who has shown improvements at the plate each year, Gregorius seems like the ideal extension candidate. They might prefer to go year-to-year with him, but I’m in favor of trying to lock Gregorius in long term.

What do you think? Should the Yankees try to extend Didi? Let us know what you think in the comments section.

Data courtesy of FanGraphs.