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SSTN Weekly Mailbag: Trading Judge, Centerfield Help, and Realistic Trades!

By Andy Singer



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Well, here we go again. The Yankees looked dominant for two whole days…and then had a clunker to finish the series. Jordan Montgomery continues to impress even when he comes to the first inning without his best stuff, so at least we have that. On the bright side, two wins out of every three games the rest of the way will get the Yankees the AL East crown. Do I think that’s likely? No, not hardly, but there is enough parity in the current Wild Card race to keep the Yankees’ playoff hopes alive, and once a team reaches the playoffs, anything can happen. For that reason, I don’t expect the Yankees to sell at the deadline, but I wouldn’t be shocked to see a real shake up on the roster. That’s going to require creativity on Cashman’s part and a willingness on Hal’s part to loosen the fiscal belt. One of those is more likely than the other. I’ll leave it to you to decide which is more likely.

In this week’s SSTN Mailbag, we’ll evaluate the likelihood of trading Aaron Judge, again try to find help in centerfield, and discuss some realistic trades. Let’s get at it:

Kevin asks: Would the Yankees really trade Aaron Judge before his contract is up? More and more I see people writing and talking about it but I don’t think the Yankees would actually do it. Does it help the roster refresh to trade Judge?

There have been a few articles lately in prominent publications recently that have mused about the potential return in an Aaron Judge trade. I am not going to say that the idea is completely without merit, because there are valid reasons to be concerned by Aaron Judge’s long-term value. Over the years here at SSTN, many of us have written about Judge’s Free Agent case, which is complicated by his injury history, advanced age at Free Agency, and projecting athletic decline in one of the largest players to ever play the sport professionally. Right now, Aaron Judge is one of the 10-15 best all-around players in the sport, possibly even better than that depending on how you grade him defensively. In 2021, Judge has been healthy and as productive as he’s been in any season other than his rookie year in 2017. The reality is that Judge would command quite a haul in a trade scenario.

That doesn’t mean the Yankees should trade him, though, and that’s for both baseball and non-baseball reasons. Did the Yankees contemplate trading Derek Jeter as he approached his arbitration years in the early 2000s, despite the fact that he had likely peaked as a player? Did the Yankees nickel and dime Don Mattingly as they tried to put a winning team around him, even in his declining years? Did the Yankees not find a way to utilize Hideki Matsui as he aged, rather than cast him off as a flawed, aging player as they pursued their first championship in close to a decade? The answer to all of those questions is quite obviously no. The Yankees’ revenue-to-salary ratio has ballooned unbelievably over the last decade and a half, even when accounting for rising costs. Frankly, Hal Steinbrenner is not putting enough of the profits back into this team, and it’s the reason Yankee fans have to complain about anchor contracts. Am I okay with the Yankees overpaying Aaron Judge relative to his likely performance over the next 7 or so years? Yes! The Yankees should rediscover some semblance of reasonable revenue-to-salary ratios so fans don’t have to complain about Stanton’s contract anymore. I’d much prefer to have the focus be on the field, and the Yankees certainly have the means to make that happen.

Aaron Judge can easily be part of the core of this team for at least the next 4 seasons. That’s a guy you keep around. The Yankees have the ability to build a team around him, if they’re willing.

Gus asks: Is there any help on the way in CF? I can’t keep watching Gardy and the new guy out there. It doesn’t seem like anyone’s trading a CF yet, but will they soon?

I’m not sure any help is coming on the trade front anymore, as some of the teams that could potentially sell off a CF don’t look like they’re in sell mode yet. However, I can pass along some good news from down on the farm.

Most of you know that I have been very skeptical of Estevan Florial’s ability to help the Yankees this season. I think his issues with pitch recognition will be a major Achilles heel at the big league level, and the only way that he can work through that development is by seeing upper level pitches for a significant period of time in AAA. Well, despite the fact that Florial really struggled initially at AAA, he seems to be heating up in a big way.

Over his last 82 plate appearances, Florial has hit .338/.463/.538, with 3 HR, 17 RBI, and 7 SB. Most importantly, his walk rate (18.3%) and strikeout rate (23.2%) are among the best of his career for any stretch. It may be a flash in the pan, but it could also mean that Florial is finally turning the corner at the plate and fulfilling some of his enormous potential. He projects as a plus defender, so if he’s even a slightly below average hitter, he’s better than anything the Yanks have had in CF this season. Don’t be surprised to see Florial in the Bronx by the end of July.

David asks: Are there any realistic trades the Yankees can make to shake-up the roster and improve the Yankees chances of a playoff run?

I’m just not sure yet what’s going to be available on the market. However, while I’m not sure the Yankees will actually shake things up, I think there are two teams who could be interesting trade partners for the Yankees: the Cubs and the Royals. Both teams will likely be in sell mode by the trade deadline, and both have targets who could be of interest to the Yankees.

If I’m Brian Cashman, I want defense, a left-handed bat, and an ability to get on-base. They may not be able to check all of those boxes in one player, but here’s two I’ve got my eye on:

Ian Happ, Cubs, OF/IF

Andrew Benintendi, Royals, OF

Happ is having a bit of a down year at the plate, but he is a switch hitter who plays good defense in CF (and passable infield defense at 2B and 3B), and has a history of positive performance at the plate. Plus, he comes with two more years of team control after 2021. His stock is low right now, so the Cubs may hesitate to deal him, but I’d bet on a second half bounce back.

Benintendi is having a resurgence with the Royals, showing good energy while making contact and getting on-base. He bats left-handed and typically runs the bases well, all things that would be welcome additions to the Yankee lineup.

The Yankees have prospects they can spare, so both of these guys would be on my short list.

#AaronJudge #EstevanFlorial

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