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Ask Pinstripe Alley 6/23/18: Brandon Drury at Triple-A, Matt Boyd trade target, Yankees prospects turned busts

Our Yankees mailbag is back with answers to a bunch of your questions!

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Ask Pinstripe Alley

Earlier in the week, I put out a call for Yankees mailbag questions. We received over a dozen responses! I’m going to answer as many as I can this morning, but don’t feel bad if I missed yours. Another edit could give it a try later in the week.

Josh asks: Am I the only one upset Brandon Drury is wasting away in Triple-A while his at-bats are being given to Neil Walker? Drury could easily be giving Miguel Andujar, Greg Bird, and Gleyber Torres one day off a week to get regular at-bats. His bat is an immediate upgrade from Walker. Is this a possibility going forward?

I know you’re not the only one upset about Drury spending so much time in Triple-A. He isn’t happy either.

“I don’t belong here at all,” he told Marc Carig of The Athletic (subscription required). “I do believe that through all this stuff I’ve been dealing with, it’s going to make me a much better player in the end. Keeping that thought and that process in my head is what keeps me going.”

Drury has a point. As of Friday afternoon, he was hitting .338/.446/.500 with three home runs (172 wRC+) for the RailRiders. He’s not challenged by Triple-A pitching. Meanwhile, Walker owns a .200/.280/.280 batting line (54 wRC+) with the Yankees. He’s only appeared in 44 games, but he hasn’t exactly given the team a reason to play him.

Would it be good to replace Walker with Drury? Sure, that sounds fine on paper. I would like Drury to get regular at-bats though. Maybe he could cover Andujar or Torres for a day, but the team almost has to get them into the lineup on the daily, right? A platoon at first base with Bird could make some sense, but it doesn’t seem likely. I suspect this will be resolved following the trade deadline. Until then the roster crunch will likely remain foggy.

Turn2intampa asks: How about Matt Boyd? Big, left-handed starter from Detroit — he would look good in pinstripes.

Boyd, 27, has made 14 starts for the Tigers this season. He owns a 3.63 ERA, but has some scary peripherals. His 4.02 FIP is okay, but he doesn’t strike many batters out (7.26 K/9) nor does he get a lot of groundballs (31.3% rate). His velocity is also down across the board in 2018.

Credit: Brooks Baseball

“Adding and subtracting is something I was working on all spring,” Boyd told Jason Beck in April. “We have a game plan on what we’re trying to do, and I will take each guy a little bit [different].”

Maybe that’s intentional, but it coincided with a noticeable drop in whiff percentage. He isn’t getting as many swings-and-misses as he did last year, especially on the changeup. His surface numbers seem fine, but there are a few scary trends underneath the hood.

As a left-handed pitcher who isn’t arbitration eligible until 2020, Boyd can be enticing. He’s relatively young and controllable, but there are some legitimate questions about the quality of his stuff.

Chris asks: With so much talk about prospects and Andujar and Torres looking like they’re making it, [how about] the flip side? Which prospects broke your heart? Who did you love and convince yourselves that was going to make it, and then just never did?

This has to be Jesus Montero, right? Like many other fans, I convinced myself that he was the next great Yankees slugger. He had such a powerful swing, and while concerns existed over his catching, it was easy to dream on him mashing dingers for a long time.

The 2011 tease felt so real, too. He hit .328/.406/.590 with four home runs in 18 games. That’s a 166 wRC+. Remember when he launched his first two career homers in the same game? That was fun.

The Yankees ultimately sent him to Seattle in a trade for Michael Pineda. I had a lot of thoughts about that deal. Montero’s career ultimately cratered, and he played his way out of baseball. He was released by the Generales de Durango of the Mexican League this spring. It’s a shame. Montero had star potential.

The Gregorius B.I.G. asks: Do we have any idea why the Yankees are good at scouting and developing now? It all seemed to start at a watershed meeting about five years ago, but what did they actually do to improve? All I’ve heard is that the scouts carry around tablets with cool proprietary software now. Did they hire away the best personnel from other teams?

That watershed meeting you speak of took place on August 20th, 2013. Hal Steinbrenner convened the front office to meet in Tampa for a complete audit of the farm system. One source described the gathering to the New York Daily News as “...a preliminary session and the beginning of a process in which they’re evaluating the entire player development department and all that’s been going on with their scouting, drafting and developing over the past seasons (since Cashman was given full control of the minor league department from George Steinbrenner in 1995).”

Shortly thereafter, the Yankees named Gary Denbo the team’s Vice President of Player Development. Under his watch, the organization transformed into a big league developing powerhouse. Top prospects turned into elite superstars — see Gary Sanchez, Aaron Judge, and Luis Seveirno — while unheralded signings became productive players. We don’t know a whole lot about what went on behind the scenes, but Denbo clearly made it work.

The scouting process in itself stands out as a fascinating story. For details on that, I highly recommend Bryan Hoch’s The Baby Bombers. Hoch talked to a number of scouts and learned about their life on the road. If that sort of thing interests you, give his book a read.

NYCKING asks: Over/under 4.5 Yankees named to the All-Star Game?

My gut reaction says the under. Judge and Sanchez should be locks at their positions; the catching crop is so bad that Sanchez’s struggles shouldn’t rule him out. Then I think on the pitching side the Yankees will send Luis Severino and Aroldis Chapman. It’s possible that Torres will make the team as a reserve. Maybe Dellin Betances will get in as well. For now, though, I’m going to play it safe and say under.