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SSTN Weekly Mailbag: Trade Deadline Questions

By Andy Singer


OK, this wasn’t the way I expected to start the 2nd half of the season. The Yankees were looking to get a hot start against Boston, but instead, we’re talking about canceling games because a significant percentage of the team has tested positive for COVID. Most importantly, I hope all of the players who have tested positive make it through their illness without complication. However, the 2nd half now begins on a similar sour note to the end of the first half. I was looking forward to possibly seeing Trey Amburgey suit up as a lefty-killing option against a heavily left-handed Red Sox pitching staff. Now that’s delayed a bit. Let’s just hope for a return to normalcy soon.

As always, thanks for the great questions, and keep them coming to In this week’s SSTN Mailbag, we have a few questions about the trade deadline and player values more generally. We also discuss a fun thought experiment that involves Giancarlo Stanton and Bryce Harper. Let’s get at it:

Paul asks: Assuming you are forced to trade Aaron Judge, what would be the best realistic trade you can think of?

OK, I’ll begin this answer the same way that I did last week’s answer regarding Aaron Judge: there isn’t a person in the world that could force me to trade Aaron Judge if I were GM of the New York Yankees. From both a baseball and marketing perspective, trading Aaron Judge is a lose-lose proposition no matter how you cut it. However, I do think it is important to understand his value from a baseball perspective, so let’s tackle Paul’s question.

First, let’s talk about who Aaron Judge is from a bottom-line perspective. Including his 2017 rookie year, Aaron Judge has a .954 OPS, 154 OPS+, 136 HR, elite walk rates, vastly improving strikeout and chase rates, and he’s a premium defensive right fielder who can fake it in center field occasionally. On a rate basis, Aaron Judge is one of the most valuable players in the sport, and Judge averages 5.5-8 WAR per 550-600 plate appearances by just about every publicly available WAR calculation. However, it is already his age-29 season, he only has one more year of team control, and he is likely to command $25+ million on a long-term deal in Free Agency. Further complicating matters is an unsettled CBA which will likely shift the financial landscape across baseball and the reality that no one really knows what the aging curve for a player Judge’s size will look like.

For all of the reasons above, there really isn’t a good comp for an Aaron Judge trade. Some might point to the Red Sox’s trade of Mookie Betts, but that was a pure salary dump at the time (any argument to the contrary is revisionist history as far as I’m concerned) because the Red Sox were unwilling to saddle themselves with Betts’ contract. Ditto for Cleveland and Francisco Lindor, who is a less valuable player than both Judge and Betts anyway. In both cases, Cleveland and Boston had tanked their leverage for a trade. Furthermore, everyone knows that the Yankees have the money to pay Judge whether they want to or not, and the Yankees recognize Judge’s value in the New York market. For that reason, the market value for Judge is significantly higher than either Lindor or Betts, regardless of the factors that could diminish Judge’s trade value.

One factor that was abundantly clear in both Cleveland and Boston’s trade demands though was solid MLB-ready talent and high upside minor league talent. If we boost the value on both ends of that assumption, we can begin to see what Judge’s value could be. I am also going to assume that the Yankees would be rebuilding if they were to trade Aaron Judge, though I expect that the rebuilding effort would be of the fast variety (think 1-2 seasons).

I’m going to use Yankee prospects in a trade proposal, as most of you reading a Yankee-centric blog are more familiar with Yankee prospects. For the low-minors lottery pick, it would have to be someone with significant tools with a higher than typical chance of making it to the Majors. The deal starts with a Jasson Dominguez-type talent in the outfield.

Now, we need to add a young, Major League-ready piece. The closest prospects like that from a value perspective are Oswald Peraza and Estevan Florial. Peraza has more upside, plays SS (the most defensively valuable position on the diamond), and is likely just a year away from making his Major League debut, so let’s include Peraza.

Then, I think we’d want two upside arms, one close to the Majors, one further away. Pitchers round out trades like this because they have less value due to their propensity to get hurt. Pick one of Luis Gil or Luis Medina. I’m a bigger Medina fan, but Gil is closer to the Majors, so let’s say Gil. Yoendrys Gomez is a pitcher in the low minors with tons of talent, but less certainty due to a lack of a third pitch and some injury concerns. He’d be the fourth piece to close out a deal.

So, even with the factors that mitigate Aaron Judge’s value, I think an offer that starts with players like Dominguez, Peraza, Gil, and Gomez at least would get the conversation started. I even think I’m a little light, but says I’m pretty close. Yes, Aaron Judge would likely get a huge return in a trade, but I still don’t think it would put the Yankees closer to a championship.

Cary asks: Being realistic, “if” the games leading up to the trade deadline, which are exclusively against teams the Yankees are 8-15 against so far ytd, don’t go well and the Yankees sink into a deeper hole – it’s possible that Brian Cashman becomes a small scale seller.

The Yankees have lots of arms other teams might covet & they also have pitchers on that list they might want to build around going forward (thinking Green & Loasiga). That said, would Lucas Lutge, Domingo German, possibly Aroldis Chapman, Zach Britton, Justin Wilson and Darrin O’Day be the most likely pitchers on the block?

I think that Wilson could be a gonner even if the Yankees are in buy mode at the trade deadline. I wasn’t a fan of the move in the first place, and Wilson has done nothing to improve my confidence. However, he’s an easy salary to move to offset any salary coming back in a deal the Yankees make, so Wilson is far from chained to the floor.

Beyond that, I think Green, German, Loaisiga, Britton, and Chapman all have value (in descending order) at the trade deadline. O’Day is hurt, so he’ll have no value for the remainder of the year, and Luetge is an easily replaceable arm.

In particular, Green and German could be valuable trade chips come deadline time if the Yankees decide to sell modestly. Green has been an elite reliever for years (last weekend notwithstanding), and many contending teams would kill to have him in the back of their bullpen. German can be valuable as a starter or a reliever and is cheap for a couple of years still, so he’ll be valuable regardless of whether the Yanks sell or not. From there, Chapman and Britton’s value are mitigated by salary, age, and injuries, while Loaisiga has an arm held together by thumb tacks (as much as I like him). That’s pretty much how I break it down.

Rudy asks: [A] strange thought just popped into my head re the trade deadline. Would you trade Bryce Harper straight up for Stanton?

This one is a lot of fun! Obviously, a trade like this wouldn’t happen now, but it’s a fascinating thought experiment just because of how much both players have been discussed in the Yankee Universe over the last 3+ years. Let’s start with a blind comparison of their 2018-2021 seasons:

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Click to Enlarge

The two players are pretty darn close! Player 1 hits for more power and a bit more overall value offensively while also displaying better plate discipline, but he doesn’t hit the ball as hard and hits for a lower BABIP. Player 2 smokes the ball with consistency, which likely helps him with a higher BABIP, which likely means he’ll produce offensive value for longer. Care to guess who is who?

Player 1 is Harper, Player 2 is Stanton. Frankly, I was shocked to see that Stanton’s BABIP was so high given his lack of ability to run anymore, but there it is. When you look at the batted ball data, Stanton sprays the ball all over the place at line drive launch angles, which makes him almost un-shiftable, while Harper pulls almost everything, making him a player that’s easy to shift against.

Both players have anchor contracts, with an equal number of years that will likely be brutal. Both are likely on the tail end of their prime’s and neither has any defensive value anymore, though at least Harper can fake it in the outfield.

Frankly, I think this is a push, but I’d still probably take Harper based on age and handedness. At the end of the day though, value-for-dollar, Stanton may actually be the better buy if he stays on the field (which is a big if).


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