When Brian Cashman orchestrated a three-team trade that sent Shane Greene to the Tigers and Didi Gregorius to the Yankees, he couldn’t have known how good the shortstop would turn out to be. After all, Gregorius hit just .241/.314/.368 during two partial seasons with the Diamondbacks before coming to New York. Flash forward three years, and he has become one of the best shortstops in the league. It is time for the Yankees to start working on a contract extension with him before he becomes a free agent in 2019.

Over the weekend, Gregorius said that he is ready to get the conversation started. He would prefer to stay in New York long-term, however, the Yankees have not discussed an extension with him yet. “I have no offer. Nothing. No talks. I’m just playing the game.”

It would be foolish of the Yankees to not at least check in with their shortstop, regardless of what their future plans are. Not only has Didi improved each year, but he is currently the Yankees’ best hitter. Gregorius is off to a blazing hot start in 2018. Through 30 at-bats, he is slugging .900 with three home runs and nine extra-base hits. Beyond that, his defense is solid, and he is a great clubhouse guy. As an added bonus, he runs the best Twitter account on the team.

On the other hand, it’s entirely possible that the Yankees will let him walk if they are able to sign Manny Machado over the offseason. It’s no secret that Machado and the Yankees have interest in each other. He grew up idolizing the Yankees, and New York was in contact with Baltimore over the offseason when they raised the idea of trading their star player. Aaron Judge even weighed in on this a few weeks ago when he said that Machado would “look pretty good in pinstripes.”

It doesn’t appear that there is room for both Machado and Gregorius on the team, though. While Machado has primarily played third base in the majors, he finally moved back to his natural position at shortstop and intends to stay there. “I moved over for a reason. I made a commitment to it, and I’m going to stick to it.”

It’s possible that Yankees money could convince Machado to move back to third base, but if the Yankees have to choose between the two, I’d rather see Gregorius stick around. The Yankees aren’t hurting for infield depth at the moment, and Didi would obviously be the cheaper option. Instead of focusing on Machado, the Yankees should look to improve their rotation. Dallas Keuchel will be a free agent after this season, and Clayton Kershaw may decide to opt out of his contract. It would be fun to see Machado’s bat in the lineup, but the Yankees should prioritize signing a starting pitcher.

Do you think the Yankees should offer Gregorius a contract extension? Do you see room for both Machado and Didi on the team? Let us know in the comment section.