The Good News
Unlike heading into the 2015 season when the Yankees weren't exactly sure how they were going to replace certain soon to be Hall of Famer Derek Jeter at the shortstop position, New York now has a clear-cut answer in the form of Didi Gregorius. Acquired last offseason as part of a trade involving Shane Greene, Gregorius had more than a solid first season with the Yankees, finishing the year hitting .265 with 24 doubles and nine home runs, and playing better than average defense along the way.
However, it was the way he finished his debut season with the Yankees that has the organization in a good spot at the position. He hit a remarkable .294 and posted an OPS nearly 150 points higher after the All Star break. Considering he still has yet to hit his prime either -- he doesn't turn 26 years old until February -- unlike a year ago the Yankees will head into a new season not really having to worry about the shortstop position, especially now knowing that Gregorius can handle the "pressure" of playing in New York.
That is certainly good news as the Yankees now don't have to rush any of their talented shortstop prospects up the minor league ladder in an attempt to find more production at the position; they clearly have at least a short-term answer in Gregorius, if not a long-term one too given his young age.
The Flip Side Of The Gregorius Coin
While having Gregorius entrenched at the shortstop position is great news indeed in terms of not having to rush the shortstop prospects coming up behind him, there is a flip side to that benefit; not having to move guys along quicker can and will most likely be problematic playing time-wise given the sheer number of quality shortstop prospects in the organization.
The Yankees entered the 2015 minor league season having to find enough shortstop reps for the likes of Abiatal Avelino, Tyler Wade, Vincent Conde, Jorge Mateo, Angel Aguilar, and even Thairo Estrada in the long-season leagues at the A-ball level. Given the volume of shortstop prospects, we opined before the season began that at least one of them would have to begin the year in Extended Spring Training and later play in the short-season leagues, and that wound having Estrada as the odd man out.
Even with holding Estrada back -- and he arguably was in fact held back given his skillset -- the Yankees still had to find ways to give the remaining shortstop prospects enough at-bats. That meant finding time by playing some other positions too. Avelino wound up playing 61 games at second base this past season [and 10 games at third base], Wade played 24 games at second, Conde played 51 games at second base and another 16 at third, and Aguilar played 26 games at second base and another 13 at third base.
Only Jorge Mateo played solely at shortstop, not too surprising given we ranked him first in the 'pref list' in this very same article last offseason. However, while exposing the other shortstop prospects to other positions can be a good thing in terms of increasing their versatility and positional flexibility, it does take them away from further mastering their defensive craft at their primary position and it's a point that can not be overstated; they're losing important development time.
Not having to move those shortstop prospects along any quicker given the fact that there is no big league need at the position can have a detrimental stalling effect down the road.
The Dilemma Continues To Grow
The Yankees handled their shortstop dilemma about as adeptly as an organization could have in 2015. However, while nearly all of the aforementioned shortstop prospects have seen marked improvements in their respective games, the same can be said of the next wave coming up right behind them and the problem in finding all of these shortstop prospects the necessary playing time is only getting worse as times goes on.
Sure the likes of Jorge Mateo, Tyler Wade, and Abiatal Avelino are poised to make their way further up the minor league ladder and seem ready to supplant the no longer needed services of Cito Culver and even Ali Castillo at the higher minor league levels so there will be some reprieve in the long-season leagues in general, but now just as talented shortstop prospects [and perhaps arguably even more talented] are immediately coming up right behind them, and there's no lapse in the depth there either.
Estrada, held back in the short-season leagues this season, acquitted himself admirably, hitting .267 with a team-high 17 doubles for the Staten Island Yankees. Throw in the fact he walked  nearly as many times as he struck out  and batted third in the lineup despite being the youngest everyday position player on the roster and one of the youngest in the entire New York Penn League, holding him back another season would not only be a waste of talent but certainly detrimental to his development. He needs to move up to the long-season leagues.
Hoy Jun Park, the Korean teenager signed last year as one of the top International free agents, also did an admirable job in his debut season this past year for short-season Pulaski, hitting .239 with eleven doubles, five home runs, and twelve stolen bases after essentially bypassing two minor league levels. Throw in the fact he walked  times nearly as much as he struck out , and the fact that his exit velocity was among the best not just in the Appy League this year but in all of minor league baseball, suggests there's some serious potential yet to be tapped. He really needs to move along to the long-season leagues too.
Kyle Holder, this year's second round pick out of the University of San Diego, is about as defensively ready as they come at the position. In fact, defensively he is big league ready right now. And while he hit just .213 in his debut season with the Staten Island Yankees and even though the majority of the aforementioned shortstop prospects have much higher offensive upsides, he does show good contact rates at the plate. Considering his draft status and elite defensive game, the 21-year old can't be nor should be held back in the short-season leagues next season either.
And then there's Wilkerman Garcia, another high profile shortstop signed as one of the top International signings last season. His stats in his debut season -- .281 with no home runs in the Gulf Coast League -- actually belie his top-shelf talent. He's an above average to plus defender already, he boasts above average to borderline plus speed, he has average or better power potential, and as his walk  to strikeout  ratio suggests he has serious hitting potential too. In fact, internally some team officials believe he not only could be the long-term answer at shortstop for the Yankees but some believe he might be their best shortstop prospect already.
All of the above doesn't even consider the merits of challenging Diego Castillo in the long-season leagues either. Another top International free agent signing last year, the 17-year old made a bit of mockery of the Dominican Summer League in his debut season this past year, hitting .331 with 19 extra-base hits in 56 games. Like Estrada a year ago, Castillo appears to be the odd man out in a potential long-season league assignment despite his already rock-solid game and lofty ceiling but is still a very important part of the overall shortstop depth in the Yankee farm system.
That leaves the Yankees with a minimum of nine qualtiy shortstop prospects who either have the talent or the resumes to be challenged in the long-season leagues in 2016 and yet they have just four teams to accommodate them. That't not even taking into consideration the likes of Danienger Perez, Yancarlos Baez, and Yonauris Rodriguez, three shortstop prospects at the lowever levels who have significant ceilings of their own and have experience playing in the United States already.
Having so many shortstop prospects is certainly a good problem to have but it is a problem nevertheless in terms of finding them all the necessary playing time.
A Trade Seems Inevitable
Like it or not, a trade of a young shortstop prospect [or more] seems inevitable on the immediate horizon given the success of Gregorius at the big league level so far and his youth, and the overall impressive depth of shortstop prospects at the minor league level. Finding all of them ample playing time is at the surface beyond problematic but more importantly some players will have their development stalled as a result too. One of them is going to have to be moved in the not so distant future and it's most likely a big reason why Jorge Mateo's name surfaced so much at this year's trade deadline.
None of the higher-end shortstop prospects are upper-level tested as of yet outside of Tyler Wade who had a cup of coffee with mixed results at Double-A Trenton so trading one of them now would most likely be selling lower than the Yankees would like. Whether a trade happens now though or at the trade deadline next season is a semantic debate -- it just has to happen over the next calendar year.
The three shortstop prospects that would bring back the most value right now [in order of trade value] are Jorge Mateo, Tyler Wade, and Abiatal Avelino, although there is growing support in the baseball community that Wilkerman Garcia could fit somewhere in between that trio right now. Don't be surprised if one of them winds up in trade talks over the winter and into next season; the Yankees simply can't afford to keep all of them in this growing shortstop dilemma.