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Ask Pinstripe Alley 6/29/16: Prospects, Yulieski Gourriel, and dream scenarios

This week’s Ask PSA delves into one of the top Cuban names available, high impact prospects, and a couple “what could have beens.”

Brazil v Cuba - World Baseball Classic First Round Group A Photo by Koji Watanabe/Getty Images

Thanks to everyone who submitted questions to the mailbag the other day! Now it’s time to dive into some of them. It’s probably more fun thinking about the Yankees than actually watching the Yankees these days anyway.

Parth Shah asked: Which current prospect has the biggest future impact with the Yankees?

The answer to this question is inevitably going to be an opinion. It depends on how much one considers ceiling, proximity to the majors, hitting vs. pitching, the overall package, and everything else. For me, the answer is Aaron Judge. I like Jorge Mateo a lot, but another contact-focused player isn’t necessarily going to be the difference-maker. I also really enjoy watching Gary Sanchez play, and he could be an important cog if he locks down the catcher’s position.

That being said, Sanchez doesn’t have quite the pure power of Judge. The right fielder also as superior plate discipline, as Sanchez has only walked in 4.8% of his plate appearances this year compared to 10.5% for Judge. Judge is going to strike out a lot and he probably won’t be a regular .300 hitter, but that’s okay. Jorge Posada hit .273 in a very hitter-friendly era, but his good eye and 275 career homers made that more than acceptable. Look at the Cubs—they built their potent offense by leaning on power hitters at a time in the game when there wasn’t nearly as much power as a decade ago.

There are spots on every team for multiple contact hitters, but usually, a big bat is needed to hit the ball out of the park. The Yankees don’t really have enough of those guys for 2017 and beyond aside from maybe Greg Bird. Young power hitters like Kris Bryant, Anthony Rizzo, and Kyle Schwarber helped make the Cubs’ amazing run last year possible. Bryant and Rizzo are special talents, but Judge is still the kind of player who can instantly put a team up by three instead of one. There will probably be an adjustment period whenever he is promoted to the majors, but if fans can be a little patient, they should be rewarded.

NYCKING asked: If you could have a one player from each AL East rival to play on Yanks for rest of season who would it be?

Manny Machado, Manny Machado, Manny Machado, and Manny Machado.

Okay fine, so I can only take Machado once. I’d also take Josh Donaldson off the Blue Jays, Mookie Betts off the Red Sox, and I suppose Evan Longoria off the Rays. The infield and outfield suddenly got a lot better (in this scenario, I’m moving Donaldson to first base). Jackie Bradley is having a superior season to Betts and I lean toward Xander Bogaerts perhaps being the best of the three in the long-term, but Betts covers an outfield spot and is terrific on his own.

It’s unfortunate that with Chris Archer and David Price’s shaky years, I can’t quite justify taking a pitcher, but so it goes.

TommyJohn asked: Should the Yankees offer Yulieski Gourriel the type of deal they gave Chase Headley?

I go back and forth on Gourriel. He is one of the greatest players of all time from Cuba, but he is also already 32, just a month younger than Headley himself. Over the next four years, if I had to bet, I would say that whatever Gourriel has to offer will be better than Headley. However, he is still certainly a risk since it’s certainly possible that a declining Gourriel now forced to face MLB pitching will not be as great (and now that he is over his 2015 yips, Headley is still a fine defender at third).

So I lean no on a four-year, $52 million deal for Gourriel, but I certainly wouldn’t fault the Yankees for giving it a shot (it’s not my money after all). I think if Headley hadn’t rebounded so well over the past two months, the team might consider it more, but since he did, the team would rather keep their regular third base investment. Maybe because Mark Teixeira will be gone in 2017, they could work something out where one of Headley or Gourriel finds extra time by sharing first base with Bird in wake of his shoulder surgery. I just don’t see that happening though. (I would definitely encourage going after his younger brother Lourdes after his 23rd birthday in October though.)

Greg asked: If you could magically undo one move the Yankees made from the last 10 years, which move and why?

On November 2, 2011, the Yankees allowed a lefty swingman in their minor league system to walk as a free agent after spending the last four years in their organization. No one gave the decision a second thought at the time, as he was decent in A-ball but not exactly a standout guy or even a prospect of note.

One week later, he signed with the Chicago White Sox. After impressing in Double-A, they decided to give him a shot in their starting rotation. Jose Quintana has been there ever since and is one of the most underrated southpaws in baseball. Realizing what they had, Chicago locked him to a ridiculously good five-year extension worth just $26.5 million. He is signed through 2018 with inexpensive options through 2020. That is a steal.

Sure, the Jacoby Ellsbury contract and a couple other deals have been ugly, but that’s just cash to the Yankees. They can get over that. They can’t get back several good years of a guy who would have been a tremendous cheap asset in their rotation. So that’s my pick.

Bonus question from Parth Shah again: Which Mexican restaurant chain reigns supreme and why? (Chipotle, Qdoba, Moe’s, Bolocco, Taco Bell (shudders), etc.)


1. Qdoba
2. Chipotle
3. Moe’s
[big gap]
66. Taco Bell

I’ve never even seen a Bolocco, so I can’t help you there. Barberito’s is a good chain too that I might be tempted to put over Qdoba, but I don’t think I can really count it among these since it’s only in the southeast. Qdoba gets the very narrow edge over Chipotle (which I do love) because they do solid quesadillas as well. I’m not saying I would never have Taco Bell, but I’d have to be pretty desperate for food. Or drunk.