New York Yankees: Should they extend Didi Gregorius this off-season?

NEW YORK, NY - AUGUST 17: Didi Gregorius #18 of the New York Yankees celebrates his RBI triple in the first inning against the Toronto Blue Jays at Yankee Stadium on August 17, 2018 in the Bronx borough of New York City. (Photo by Elsa/Getty Images)
NEW YORK, NY - AUGUST 17: Didi Gregorius #18 of the New York Yankees celebrates his RBI triple in the first inning against the Toronto Blue Jays at Yankee Stadium on August 17, 2018 in the Bronx borough of New York City. (Photo by Elsa/Getty Images)

With the New York Yankees re-setting the luxury tax penalties, should they look to extend Didi Gregorius this off-season?

The New York Yankees are in prime position to reset their luxury tax penalties this off-season and still have the second-best record in all of baseball this season. What’s helped is the fact that they have been able to develop their own talent through trades, the draft and international free agency.

The thing is, that young talent is going to get more expensive in short order. Luis Severino and Greg Bird will be arbitration eligible for the first time this off-season. One of their core players is going to be a free agent after next season in shortstop Didi Gregorius. Should they look to extend him in the off-season?

Coming into today, the 28 year old shortstop is hitting .268 with an .813 OPS which would be a career high. He also has 22 homers and 73 RBI and if he remains healthy, will certainly set career highs in those categories as well. His UZR of 5.6 is fifth best among shortstops as well this year.

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Gregorius has also become one of the faces of the New York Yankees franchise and a fan favorite with his victory tweets and emojis for each player.

He’s become one of the best shortstops in the game on both sides of the ball and is in the middle of his prime. You also have to look at who would you have internally to replace him should he leave. Would they move Gleyber Torres back to shortstop as he’s starting to establish himself as a second baseman? Is Tyler Wade a future regular, or is a super utility player as the New York Yankees have tried to develop him.

There’s also the pending free agency of Manny Machado who the New York Yankees have had their eyes on.

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As good as Gregorius has been, I believe an extension is something the New York Yankees should look at. A five or six year deal wouldn’t be crazy and four win players don’t grow on trees. He’s making over $8 million this year, would a five year or six year deal around $15 million per year get it done? It certainly could.