The Case to Extend Didi

Yankees Shortstop Didi Gregorius has proven himself since arriving in the Bronx in 2015. He made (most) people forget about Derek Jeter. Now we have to consider giving him an extension at the end of the year. Here are a few reasons why Cashman should do it:

1.) Great 2017

Didi Gregorius is on pace to have his best season yet. He currently has a slash line of .303/.330/.506 with 17 homers, 53 RBI's and a 2.7 WAR. Over a full season that roughly projects to 28 homers, 88 RBI's and a 4.5 (!) WAR. A lot of that value comes from that fact that he is a crazy good defender. Oh and he's one of the most colorful personalities/best teammates in the clubhouse. There's a lot to like about Sir Didi (including his Twitter account) in his age 27 season.

2.) Growth

While this year has been incredible, it's not just about 2017. It's about the buildup to 2017. Didi has improved every single year with the Yankees. He went from .265/.318/.370/.688 in 2015 to .276/.304/.447/.751 in 2016 to .303/.330/.506/.837 this year. That's some serious growth, especially in the power department. Sir Didi has shown no signs of slowing down, and, at age 27, he is in his physical prime. There is good reason to expect this growth to continue throughout his prime.

3.) Saves Money

Time could be running out to extend him at a team-friendly price. If we extend him this offseason, we would be buying out 2 years of arbitration, which would lower the price. Didi doesn't have a huge track record of high-end success yet, so that would lower the price. In addition, there is a history of shortstops signing team friendly deals to buy out arbitration years. Examples:

-Jean Segura: 5 years, $70 million after 2 arbitration years to buy out 2 more plus 3 more years

-Brandon Crawford: 6 years, $75 million after 1 arbitration year

-Hanley Ramirez: 6 years, $70 million to buy out all arbitration years plus 3 more years

Other SS extensions of note:

-Elvis Andrus: 8 year, $120 million at age 26 with a couple opt-outs

-Troy Tulowitzki: 10 year, $158 million at age 25

The best comp by far is Jean Segura's extension for a few reasons. A) It's the most recent SS extension. B) Didi will have the same number of arbitration years left if he is extended this offseason. C) Segura and Didi are decently similar players who are both 27.

With all that being said, let's try to build a deal for Didi. First, the length. 5 years is pretty standard, though I'm comfortable giving Didi a 6-year deal especially if it means paying him less. The Yankees could try the Elvis Andrus route with a bigger deal with an opt-out or two. However, those kinds of deals always seem to end in a lose-lose situation (see Tanaka, Masahiro). So let's say it's a 6-year pact.

Now onto money. Didi will get more money than Segura because he will sign after Segura, and will become a better player if he isn't already.

The way these extensions are usually structured financially are different than free agent deals. The first couple years are generally cheaper because they would be arbitration years had the extension not been signed. Then, the contract incrementally increases in value to reflect the real talent level of the player. Take Tulowitzki's deal as an example:

Year 1: $5.5 million

Year 2: $8.25 million

Year 3: $10 million

Year 4: $16 million

Year 5-9: $20 million

Didi obviously won't receive a contract of this magnitude, but you get the idea. This is what I would pay to lock up Didi:

Year 1: $8 million

Year 2: $11 million

Year 3: $16 million

Year 4: $16 million

Year 5: $16 million

Year 6: $16 million

$2 million signing bonus

Total: 6 years, $85 million

With this year, Didi earns slightly more annually than Segura and clearly more than the defense-first Crawford. And he receives a signing bonus. He should be happy.

In a world with expensive free agents, this is a reasonable extension, especially given Didi's potential moving forward. Didi is satisfied, and we have our shortstop of the future locked up. It could even turn into a bargain for the Yanks. That's what you're looking for in an extension.

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