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Two Insiders Break Down the Prospects who are the Yankees Most Desirable Trade Assets Ahead of the D

Guest Post from Cary Green

July 20, 2021

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I recently had dinner with two Major League Baseball “insiders.” One is a long time friend and client and the other was a friend of his. We met up at “Oystercatchers” restaurant over on Bayport Drive in Tampa, Florida for Sunday Brunch the morning after catching a Tarpons game. (I had the Crab Florentine Benedicts with the ancho chili béarnaise, served with breakfast potatoes by the way and was not disappointed.)

What I am about to write regarding my two friends’ opinions is obviously under the condition of anonymity, even though I picked up the check!

As for my opinions, I promise not to hold back!

The short of my report is that there are certain prospects that MLB scouts doubt the Yankees would part with and not all of those prospects are players that insiders think the Yankees should necessarily keep. I found that to be very interesting. There are also extremely valuable prospects that scouts think could be had very easily from the Yankees and insiders expect many rival GM’s will be targeting this short list.

The Tarpons hosted the Lakeland Flying-Tigers in a “Low-A” level ballgame this past Sunday, in a game that started at Noon at George M. Steinbrenner Field. It was the perfect day to attend a baseball game – temps in the low mid 80’s and partly cloudy skies.

Jason Dominquez roped a single and we also got to see the Yankees #9 prospect Yoendry’s Gomez pitch for the Tarpons against the Tigers #38 prospect, Jose De La Cruz. The Tarpons won 5-4 in a very cleanly played game in which nearly 20 year-old center-fielder Everson Pereira, the Yankees #18 year old prospect, had the key two-run single. Pereira was the designated-hitter and went 2-4 with two singles and a walk against no strikeouts.

Over brunch, the two MLB insiders were discussing various players and taking notes, when I brought up the topic of which Yankees top prospects would they most likely target in any trades their teams would make with the Yanks. I asked who they would take.

They quickly machine-gunned through the top Yankee prospects and pretty much unanimously identified the most appealing trade targets. I noticed neither had a very high regard for analytics, which I thought was interesting. The discussion was about the players’ abilities – as seen by people who know baseball. They based their opinions about what happened on the field of play.

Jason Dominguez’s name came up first. They both identified the 18-year-old outfielder, who is the Yankees’ #1 overall prospect, as being untouchable and even chuckled at the notion that Brian Cashman would trade him. He’s not going anywhere.

They also seemed to be in agreement that playing for the Tarpons was going to be a huge challenge for Dominguez, mainly due to him being only 18-years-old. One said, “Every scout in baseball is curious about Dominguez, because we haven’t seen him yet, but everybody’s waiting to see how he handles the pressure and the expectations, even more so than the pitching – which will be by far a hundred times better than anything he’s ever seen up to this point in his life.”

The other said, “Totally and while there is no doubt as to his tools, the hype is either going to skyrocket or it’s going to evaporate completely after a few months, and who knows, he may become realistically touchable or he may really be the next Mickey Mantle.”

Not surprisingly the next name that came up was 25-year-old Clarke Schmidt, who is now widely regarded as the Yankees’ next best prospect, slotting in at #2 overall in the Yankee system. Both insiders seemed to think last year hurt him tremendously, because, “He needed innings and he didn’t get them.” They went on to say, “Now Schmidt is injured again. That’s really hurting his ability to improve. We’d still target him in a trade because he projects as a mid-rotation, or better, starter but he’s got to prove he can stay healthy and that’s a big concern with him at this point.”

The conversation then turned to Deivi Garcia. One of the experts frowned and the other took the opportunity to dig into his Lobster Omelette which came with herbs, boursin cheese, old bay aioli, and an arugula salad. What followed was mayhem. One said, “He’s a mess.” The other said, “Yep.” The consensus was that they were both a lot higher on him last year, but each had concerns about his physicality. One said, “Garcia is, at best, a #5 Starter and more than likely, he’s a long man for most ballclubs.” The other said, “He might appeal to teams that are looking to hit the jackpot on the cheap, but he’s not worth trading for, at least to me. The Yankees have a lot other pitchers I’d look at over him and I bet in the next rankings update, you’ll see him fall easily outside of the Yankees’ top 10 prospects.”

Unsurprisingly, Oswald Peraza, the 21-year-old AA prospect came up next. Peraza was identified as a prospect the Yankees shouldn’t be so high on. After a bit of chewing and some silence, one insider said, “Cashman’s never trading Peraza, the Yankees love him. He’s still young for AA baseball, but for me, I don’t think he looks good against breaking balls. Every time I’ve seen him, his swings look awful against curves and change ups. I could see him completely stalling out at AAA. Major League pitchers would just drub him with off-speed stuff. He’s a fastball hitter right now and that’s it. End of the story.” The other insider nodded and didn’t even say a single word. Then, he said, “Gleyber Torres was way more advanced with the bat in AA ball. He was up there smashing balls to all fields and he had a lot better balance with his weight back. Gleyber’s leg kick is pronounced but slow and his hands are really fast.” Then the other insider said, “If I was the Yankees, I’d be more patient with Gleyber this season and then maybe move him to second base. The problem with that though is, what’s Cashman going to do with DJ LeMahieu?”

One thing both insiders agreed on is that they thought Peraza’s fielding is quite a bit further along than his hitting is. The Peraza conversation ending by one person saying, “Look, we’d love to have him, but the Yankees’ sense of value with him is so sky high that it just isn’t worth it. The Yankees always over-hype their prospects and Peraza is one they’re doing a serious PR job on. He’s just not all that at this point.”

23-year-old righty Luis Gil’s name came up next. It was remarked, “He’s a lively arm and everybody’s going to want him in a trade, but he has a ton of learning to do. He’s a thrower and not a pitcher.” The other expert chimed in, “Analytics departments love Gil, he’s throws up in the zone with good spin rates, but he has serious growing up to do – as in years worth. Granted he’s now in AAA but it wouldn’t surprise me to see him stay there all of this year and at least until September of 2022. He’s nowhere near ready to face patient major league hitters with those walk rates. Every time I’ve seen him pitch he’s walked 5 or 6 guys, or more even.” The other insider then said, “In my last write-up, I advised that Gil be passed on in any potential deals, in favor of Gomez or Vizcaino or maybe Volpe. Gil’s sense of knowing how to pitch is non-existent and in this league, you can’t rely on a fastball alone. Granted, he’s got a slider but his changeup is all over the place. Because of his slender frame, I just don’t know if he can handle the innings of a starter going forward. I see him as a set-up man or maybe a closer down the road.”

The conversation then turned to Austin Wells and if I had any doubt that I was in the company of truly professional baseball guys, it evaporated with what was said next. One said, “He’s not a catcher. I don’t know how else to say it. I mean, best case scenario is he’s an emergency catcher. The Yankees are wasting their time having him catch. We’d already have him at first base, even though he’s a right handed fielder, that’s where he belongs.”

The other insider added,” Yep and what I like about Wells is his overall command of the strike zone. He’s got an advanced eye at the plate. I think he projects as a .250 hitter with a very solid On-Base-Percentage.”

The conversation continued, “None of the higher ranked Yankees catching prospects impresses me. Wells is a first baseman, Siegler is terrible with the bat, and Breaux’s glove is really bad also. Honestly, the Yankees should extend Sanchez and Higgy because they aren’t going to get much help from their system until Antonio Gomez comes up and that’s not realistic to even think about until probably 2024. Gomez has the glovework that the other Yankee catching prospects wish they had and we’d target Gomez long before Siegler, Wells, or Breaux. The problem is, it’s going to take a while for Gomez’s bat to get where it would need to be. He’s relied on his raw power up to this point, but his bat-to-ball skills need work”

At this juncture of the conversation, I was beginning to feel that both insiders felt the Yankees player development department was over analytics driven and quite a bit out of touch. What they were saying made sense to me also. I had lost faith in Yankee decision making some time ago. For whatever reasons, the Yankees let analytics become too influential. I wondered if internal politics in the front office, more than anything else, have hurt the Yankees most. I also wondered if Hal Steinbrenner was badly out of touch with what was really going on with his organization. I wondered if Steinbrenner is simply more impressed with graphs and charts than he is real baseball people, who can absolutely have attitudes that push back and don’t really respect or rely entirely on analytics.

Is this single issue at the heart of the Evil-Empire’s mediocrity these days?

My pondering ended as the conversation turned to 22-year-old AA starter Luis Medina. One of the experts said, “Medina can’t pitch. He’s a bullpen guy, flat out. His big problem is control and everybody knows it.” The other added, “Medina is a guy Cashman fell in love with because of analytics. He is really raw. He’s got a power arm, but so what? He can’t locate and he can’t pitch. Honestly, we wouldn’t want him at all but all it takes is for one team to fall in love with a guy. If that happens, Cashman should move him while he still can.” The other echoed,” Yep, not a guy we’d target in a trade. The Yankees think he has a lot of value but nobody I know feels he will be what the Yankees hope.”

I was beginning to see the ugly underbelly of the Yankee system. Here we were talking about top prospects and already, a number of Yankee prospects weren’t well regarded by these two insiders.

Estevan Florial’s name came up next which I thought was interesting since Alexander Vizcaino was more highly rated. One opened with, “His makeup is terrific, he’s got tools but between all the injuries and his one glaring weakness, he’s just not a major league player. He strikes out way too much, he’d never stick.” The other expert said, “The Yankees have him trying to hit home-runs and it’s pretty much ruined him. He’s got the tools to make contract but its tough to do that when you’re swinging for the fences every time you come up. At this point, I think Florial is about to become a bust and it’s too bad, because the Yankees had something with him.”

I asked a question at this point – “So fellas, is there a player we haven’t talked about that you could identify as being somebody you’d say is a super prospect, that you’d love in any trade?” They both said at the same time, “Anthony Volpe” and then everyone started laughing. The first insider said, “I really think he’s the best position player in the Yankees system. He does it all and he’s even a leader on the field. The Yankees hit the jackpot with this kid. Brian Cashman would be a fool to trade him just to help the big league team at this year’s deadline.”

The other expert added, “Volpe is a guy we’d love to trade for and he’s got a lot of value which is sky-rocketing right now”

The conversation continued, “Volpe has instincts that are rare. I think everybody’s going to be inquiring about him at this year’s deadline, where there is still a chance to steal him while his value is still such that he’s obtainable. Cashman may be in such a lather to upgrade a position of need, I feel he could be persuaded to part with Volpe.”

The reply – ”Yes and Cashman’s taking serious heat in the New York market so he may feel if he doesn’t act now, his job may be on the line.”

I was left with my fears confirmed by these two professionals. It’s possible that Brian Cashman might part with someone he really shouldn’t give up just to try to prop this team up. The entire industry might be looking to dangle someone Cashman sees as the answer to an area of need, only to fleece him by relying on their scouts to guide who they ask for in return.

I thought, is Brian Cashman the guy I want the Yankees really want making this decision?

Well, it’s a moot point, because Hal Steinbrenner is the boss in a lead from the top down organization that doesn’t like to be pushed back on and he fully supports Cashman’s decisions so perhaps the Yankees are heading into this deadline on the verge of making some enormous mistakes that will haunt the organizations future for a long time.

Desert came and our time was coming to a close quicker than I hoped it would. I had more questions to ask… However, the waitress was fast and coffee came quickly, so we lingered.

It was then that Josh Smith’s name came up. Both guests mentioned him next and one said, “I don’t know if long term, he’s best suited for shortstop – mainly because of his arm, but Josh Smith can flat out hit and he’s a real ballplayer. The Yankees are aware of this and I think we’ll see Smith move to second base at some point in his development. He’s still only 23, so there’s time for him to learn but every day that goes by with him out of position is another day of reps that he misses.” The other insider added, “Oh, we’d definitely be in on Josh Smith. He’s undervalued right now, he’s the perfect throw in for a trade to get it over the top. We’d take Smith over several other Yankee prospects ranked ahead of him and he could be had on the cheap.”

Next up came Eziquiel Duran. The first comment was, “Duran should be rated way higher in the Yankee system but we’re not complaining because we’d love to acquire him. In fact, almost everybody would take him over Peraza, that’s how good he is and its no secret among scouts.”

The reply was, “Agreed, Duran fields his position really well, he’s got speed and his bat could really play up in the future. Somebody could easily grab Duran right from under the Yankees’ noses and most of their fans and internal people wouldn’t realize it until it was too late. Because of his value, he’d be asked for in most trades I would imagine.”

With that, our conversation ended.

The food filled my belly, but the conversation filled my brain even more.

There are going to be a very interesting two weeks as we head to the deadline.

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