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Yankees Mailbag: DJ LeMahieu extension, futures of Didi Gregorius and Dellin Betances

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The answers to this week’s mailbag have arrived!

Ask Pinstripe Alley

Hello, everyone, and happy Friday! I hope you all enjoyed the holiday yesterday. Whether you’re taking the day off or having a quiet afternoon at work, let’s catch up with a mailbag. I could only get to four questions today, but keep sending them in. There’s plenty of room for next week!

George asks: When does Mr. Cashman plan to sign DJ LeMahieu to a contract extension? The guy is a proven superstar, an amazing ballplayer, and awesome and beloved team player. He is also the Yankees’—and perhaps the AL’s—MVP for the first half of the season.

I’ve seen variations of the “extend LeMahieu” conversation floating around lately, and I find it kind of funny. LeMahieu has been phenomenal—better than expected! I cannot overstate how impressed I am by his play this season. But let’s be a little reasonable.

First, the Yankees have LeMahieu under contract next year. They have no incentive to line up an extension right now. Additionally, how many years would you want tacked on to his deal? Didn’t many fans advocate against paying Manny Machado in his age-35 season? That’s where an extension would bring LeMahieu.

I would also caution fans against declaring LeMahieu the AL MVP. He’s been great, but he’s not Mike Trout. I’m sure this will lead to a lengthy exegesis over the meaning of the word value, but it’s not that difficult. Trout is the best player in the world, LeMahieu isn’t. Problem solved!

Several have asked: What do the Yankees do with Didi Gregorius next season?

In what might be a cop-out answer, I believe the Yankees will extend Gregorius the qualifying offer. I also think there’s an even chance he accepts it, too. How many teams expect to be in the market for a shortstop next year? The list isn’t terribly long. The Reds strike me as a team to watch, though. They could use an upgrade over Jose Iglesias and Jose Peraza, and Cincinnati is intimately familiar with Sir Didi. Outside of that example, I can’t find a great fit.

If Gregorius wants certainty instead of a one-year deal, I’m sure the Yankees will talk long-term contracts. I just don’t know if they will be comparable to the extension Xander Bogaerts received. They might not come in with the highest offer, and in that case, they may not keep Gregorius. That would be a shame, wouldn’t it? Hopefully they keep him around for a while.

The Gregorius B.I.G. asks: The past three years, the Yankees have used the same strategy to address first base: Greg Bird + another younger player with significant upside and downside + a decent and affordable veteran. It worked out terribly two years in a row and many fans were dismayed that the Yankees would try it again, but it has gone well this year. Now that we’ve seen how well and how poorly this strategy can work, do you think it was a good one?

Since 2017, the Yankees have had 19 different players covering a minimum of one inning at first base. If that number seems wild, wait until you see the list of names.

Credit: Baseball Reference

How about that for a blast from the past?

As you noted, the Yankees placed an odd amount of confidence in Bird. They wanted him to succeed, but brought in veteran first basemen and minor league depth pieces to cover for him. They understood the injury risk and acted accordingly. For some stretches of time it worked, for others it didn’t.

It’s difficult to fault them for the uneven performances, though, because the process was sound. The team had the luxury of taking their time at first base because the rest of the Baby Bombers played so well. The Yankees got traditional first base offense numbers from all across the diamond. That helped a lot.

Also, the first base targets over the last three years haven’t been all that exciting. The options included signing Eric Hosmer or Edwin Encarnacion? You could make the case for them, but there’s a lot of hindsight involved.

It would have worked better if Bird stayed healthy, but that just didn’t happen. That doesn’t mean it was a bad strategy though. Sometimes you can prepare well and still have no results to show from it. That is, until you swing a trade with the Cardinals. Thank goodness for Luke Voit, right?

thehiro19 asks: What do the Yankees do about Dellin Betances? Do they let him walk after this year, offer him a QO, or try to give him a proper deal based on past performance?

Aaron Boone gave an update on Betances recently, and it’s good news. He told reporters that the right-hander was around a week away from throwing, and his shoulder was about 90% healed.

If Betances returns in August, he could get about two months of the regular season to show he can still pitch at an elite level. If all goes well, I could see the Yankees giving him a qualifying offer. I’m not sure he’d accept though, because relievers still tend to get paid in this market. Look at Zack Britton—he missed a substantial portion of last season with an injury, albeit not related to his arm, and he earned a $39 million deal.

If the bidding goes any higher than that, then I’m not sure the Yankees will push to keep him. It would be a shame, because he ushered in the youth movement. In you ask me, Betances should stay a Yankee for life.