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  • Writer's pictureAndy Singer

Trade Deadline Reaction: Andy Singer

Updated: Sep 22, 2022

Photo Credit: Joe Nicholson, USA TODAY Sports

I don't think it's hyperbole to state that this was the single most exciting Trade Deadline of my lifetime. Often times there are significant rumors, none of which come to fruition. This is the first year in which I think more than half of the franchise-altering rumors that were floated came true. For those that haven't read it yet, I highly recommend reading what my fellow SSTN writers had to say yesterday regarding their reactions to the Trade Deadline in the special Wednesday Discussion. I wasn't ready to give my reaction, as my feelings about a particular deal (more on that in a minute) were sure to cloud my analytical perceptions of what the Yankees did.

I already reviewed the Benintendi trade separately last Friday (to summarize: great deal for the Yankees given the cost, even if Benintendi comes back to Earth given the likelihood that his BABIP regresses due to his propensity for weakly hit singles through the infield), so I won't analyze that deal specifically below. What will follow is an analysis of each trade individually in chronological order, and then I'll zoom out to look at the Yankees' Trade Deadline maneuvers from a macro perspective. Let's get at it:

The Trades

Monday, August 1st: Yankees trade RHP Hayden Wesneski to the Cubs for RHP Scott Effross

We all thought that the Yankees were going to bring David Robertson back for a 3rd go in pinstripes, and the logic was sound: Robertson has largely turned back the clock, using his cutter/fastball/curveball combination to accumulate excellent strikeout numbers, limit walks, and prevent runs in a sustainable fashion; the Yankees are very familiar with his medicals and personality; and he has a track record of success in playoff competition and under the pressure of playing in New York. So the Yankees made a deal with the Cubs...for a reliever not named David Robertson.

Scott Effross doesn't exactly jump off the page, but he has pitched very similarly to David Robertson in 2022, and he does a lot of things the Yankees like: he throws a devastating sinker and combines it with a whiffle ball slider that bears a striking resemblance to the whirly slider the Yankees are teaching many of their pitchers. Effross's pitch mix allows him to limit homers and accumulate more strikeouts than his bottom-line velocity would seem to indicate. Most importantly, Effross won't be eligible for Free Agency until after the 2027 season, so this move improves the Yankees' bullpen for the 2022 World Series run and in future seasons as well.

Hayden Wesneski had a really hot start to his AAA season, but he has cooled off in recent months. Wesneski has a chance to be a very solid 4/5 starter if everything clicks right, but he was not ready to help the Yankees in pursuit of a championship in 2022. More to the point, I have a hunch that even at maturity, Wesneski is the type of pitcher for whom the front office would attempt to find an upgrade long-term. Wesneski will get a chance to prove he belongs as soon as this season with the rebuilding Cubs, and the Yankees stabilized their bullpen.

Both teams got what they needed out of this deal, a rare win-win on the MLB trade market.

Monday, August 1st: Yankees trade LHP Ken Waldichuk, RHP Luis Medina, LHP JP Sears, and MI Cooper Bowman to the Athletics for RHP Frankie Montas and RHP Lou Trivino

On the surface, it might seem as though the Yankees gave away a lot to get Montas, and some fans might be further confused by the acquisition of Trivino given his dismal results in 2022. I assure you, the Yankees may have sliced into their minor league pitching depth with this move, but this trade was as good a deal as the Yankees could have hoped for.

I was very sad to lose each of these pitchers, particularly so in the case of Luis Medina and to a lesser extent, JP Sears. Those of you who have read my writing over the years know that I've been pretty close to the biggest Medina apologist on the internet since he first appeared in videos after his signing. Sure he has control issues, but Medina is athletic with some of the most electric stuff in all of baseball anywhere. Medina runs out of options next year, but I think his floor is as an impact reliever, and I remain convinced that he has advanced far enough with his fastball command and overall control to try starting at the big league level initially. Waldichuk may be the highest ranked prospect according to most popular publicly available scouting outlets (though Fangraphs agrees with me, and ranked Medina the number 3 prospect in the Yankee system), but Medina is the biggest wild card in the trade, and the guy the Yankees might regret dealing the most.

Waldichuk throws hard with a good slider and a good enough change-up to start, but he might also end up in the back of a bullpen long-term has he struggles to hold his stuff deep into outings and he still needs polishing. Waldichuk has the upside of a mid-rotation starter though, and he's likely to help Oakland as soon as next season.

I liked JP Sears more than most as he slowly made his way through the Yankee system. He displayed solid control over all of his pitches and good command of his fastball and at least his slider. What didn't come until the last couple of seasons was multiple bumps in velocity that allow him to live in the mid-90s out of the bullpen and only slightly less than that as a starter. I think the package is there for Sears to be a good back-end starter or a good lefty out of the bullpen, though his diminutive stature has some scouts worried about his long-term durability and fastball plane.

Cooper Bowman makes a lot of contact and is a really good up-the-middle defender whose arm is probably a little light for shortstop, but he appears to be a good defender at 2B. Bowman is also an excellent baserunner who steals more bases than his natural speed dictates he should. He's not a high-probability big leaguer, but the exact type of prospect the Athletics should take a chance on right now.

As good as those prospects are, the Yankees needed to bolster the rotation heading into October, as some cracks had begun to show. Frankie Montas does exactly that, as he's right there with Cole, Sevy, and Nestor in terms of the ability to dominate a game. Montas has a bowling ball sinker and a kitchen sink of offspeed stuff and breaking balls that makes it incredibly difficult for hitters to gameplan against. I ranked Montas very evenly with Luis Castillo and Carlos Rodon, the other two realistic prizes of the starting pitching market. The bonus is that Montas is around next year as well before he needs an extension. Montas > Taillon/Monty/German, and that matters in October.

Trivino has a track record of success as a closer (a pressure-packed spot), and the underlying metrics indicate that he has pitched into some really bad luck in 2022. Trivino still misses a ton of bats with an elite strikeout rate, and he has three pitches (slider, cutter, and change) that hitters really struggle to square up. The Yankees likely see an immediate place Trivino can tweak his arsenal to coax some better results (look for him to choose to focus on either his four-seam or sinker, not both) in the long-term.

In short, the Yankees made themselves a more formidable team in October with this deal, and while the Yankees exhausted some upper minors pitching depth, this is a deal you make every time if you think you can win the World Series. I'm sure that players in the clubhouse felt energized to know that the Yankees were doing everything in their power to improve in their pursuit of a World Series ring.

Tuesday, August 2nd: Yankees trade OF Joey Gallo to the Dodgers for RHP Clayton Beeter

I thought it was hysterical that some people honestly believed that the Yankees would be forced to DFA Joey Gallo. As terrible as he's been as a Yankee, the power remains, he runs well, and he's a good outfield defender. As a plus, he also has been acknowledged to be a good clubhouse presence; it just didn't work in New York, and I think other teams recognized that while his value had diminished significantly, there is real value there for a team outside of New York's bright lights. While the Yankees' return on investment is in the negatives, Beeter is an interesting pitching prospect, who I referred to as "Luis Medina Lite" to someone who asked me about it.

Beeter has truly overwhelming stuff, sitting in the mid-high 90s with plus stuff across the board, but with little feel for fastball command or general control. This means he gets hit a little too much given his high octane stuff and he walks too many batters. However, the Yankees have turned a weakness into a strength in recent seasons, proving that they are among the best in baseball at developing pitching, and I expect them to help Beeter maximize his potential. He could be a flamethrower out of the bullpen, or he may just click and become a really interesting starter. Oh, and he has options remaining, unlike Medina.

The Yankees and Gallo both needed a change of scene, and the Yankees did a good job to get something of value here.

Tuesday, August 2nd, 5:55 PM: Yankees trade LHP Jordan Montgomery to the Cardinals for OF Harrison Bader

This one shocked me as much as everyone else. In fact, Paul Semendinger and I were texting each other at the deadline with dropped jaws, sure that another last minute trade for a starting pitcher would be announced. Alas, it was not to be. In a vacuum, I think the Cards win this trade by a hair. However, we don't operate in a vacuum. I needed to cool off for a day before I analyzed this one.

Monty has long been a personal favorite, and I think he's more valuable than most realize. Monty's loss will make the rotation weaker in the regular season...but I think this trade makes the Yankees stronger in October.

It is true that Bader is on the IL right now, but the Yankees clearly believe that there is a high probability that he will be fully healthy by October. And that's really what this is about. As we have seen in recent heartbreakers in the Bronx, run prevention is everything in a short series. The Yankees' playoff rotation is greatly improved with the addition of Montas, and Bader adds a truly elite option in CF and an elite baserunner depending on the situation. I'd also add there's more untapped potential in Bader's bat, but I think that work will have to wait until the offseason.

I'm still lukewarm on this deal, as are some in the Yankee front office and clubhouse, but I see the logic.

The Big Picture

Here's the complete list of who left at the Trade Deadline:

  1. LHP Jordan Montgomery

  2. OF Joey Gallo

  3. LHP Ken Waldichuk

  4. RHP Hayden Wesneski

  5. RHP Luis Medina

  6. LHP JP Sears

  7. MI Cooper Bowman

Here's who came back to the Yankees in those deals:

  1. RHP Frankie Montas

  2. RHP Lou Trivino

  3. RHP Scott Effross

  4. OF Harrison Bader

  5. RHP Clayton Beeder

The Yankees cut into their depth and minor league system, but they only gave up 1-2 guys that realistically could have helped in October. They acquired 4 players who can certainly help in October, and more than the 1-2 other outgoing players could have. There is no legitimate analysis of the front office's moves that could come to the conclusion that the Yankees aren't better positioned for the playoffs today than they were two days ago.

I'm not even counting Benintendi here, who also deserves to be counted. The Yankee lineup is more well-rounded, the starting rotation is more powerful, and the bullpen is significantly deeper. Brian Cashman and company did a superlative job at the Trade Deadline, better than they've done in a long time.


Cary Greene
Cary Greene
Aug 05, 2022

Something else to consider regarding the Montgomery trade. John Heyman of the post reported, "It’s clear the Yankees didn’t love Montgomery (“he’s been available for a while,” says a rival). And word is, Montgomery wouldn’t have made their playoff roster. Plus Aaron Hicks (0-for-his-last-24) has become an issue again.".

So basically the Yankees traded a pitcher who wasn't even going to be on the playoff roster in order to obtain next year's starting center fielder and avoid having to stare down Scott Boris in order to sign Brandon Nimmo, who is the best available center fielder and also will be by far the most overpriced in terms of AAV.


Cary Greene
Cary Greene
Aug 05, 2022

Personally I was never high on Luis Medina. Due to lack of command, in SIX YEARS he never made it past Double-A. This season alone, 5.4 BB/9 with "only" 10K/9? If his arm is eletric, he should be striking out people at a higher clip. The 6.9 Hits/9 shows his stuff is tough to deal with, but he's perpetually beating himself with all the walks. He doesn't understand "how" to pitch and he likely never will. He's still young but for him to advance as a starter would take massive strides this season and next. Likely he winds up in the bullpen and he won't cut it there either witch such poor command. He's a thrower, not a pitcher.


Cary Greene
Cary Greene
Aug 04, 2022

5:00pm: There was no last-minute trade of either Rodon or outfielder Joc Pederson, tweets Andrew Baggarly of The Athletic. Both remain with the Giants and are now ineligible to be traded with the deadline passed. The Giants can still issue a qualifying offer to both players, with Rodon standing out as a particularly obvious candidate to receive one.

2:20pm: The Yankees have also checked in on Rodon, though they’re seen as a “long shot,” Jon Heyman of the New York Post tweets.

After the possible trade with the Marlins went south, Cashman was clearly looking for a starter. He also failed to extend Judge and there is zero guarantee that he's going to be back. A return is 50/50 at…


Aug 04, 2022

got a question

which is more likely.... that an AL East team will catch the Yankees

or that the Padres will catch the Dodgers?

Cary Greene
Cary Greene
Aug 05, 2022
Replying to

Great point about Freeman.


Cary Greene
Cary Greene
Aug 04, 2022

DiDi Gregorius was released today by the Phillies. The Yankees might want to sign him to a minor league deal and consider platooning him with Falefa, providing he starts hitting at AAA.

Paul Semendinger
Paul Semendinger
Aug 04, 2022
Replying to

I'd rather have Marwin than Didi at this point because Marwin can play multiple positions.

I love Didi. But, he's not the guy to bring back.

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