Grading the New York Yankees trade deadline

Ryan Garcia
andrew benintendi, yankees
Jul 29, 2022; Bronx, New York, USA; New York Yankees left fielder Andrew Benintendi (18) hits an infield RBI single to tie the game in the eighth inning against the Kansas City Royals at Yankee Stadium. Mandatory Credit: Wendell Cruz-USA TODAY Sports

The Yankees have had a busy deadline, making big moves left and right.  With how much pressure Brian Cashman had to make big trades and improve this team, he’s done wonders. Instead of looking at the deadline as a whole, I’ll break down each trade and grade how the Yankees and Brian Cashman did in each trade.

Andrew Benintendi For Three Prospects

Andrew Benintendi was one of the better outfielders on the trade market. With a wRC+ ranging between 120-125 this year and solid defense, Benny was a solid player to add to a team that needed a little offensive spark. They traded three pitchers, none of which were top 10 prospects in the Yankee farm system:

  • RHP Beck Way
  • LHP TJ Sikkema
  • RHP Chandler Champlain

No pitcher involved in the deal had reached AA with the Somerset Patriots, however, they still have some upside. The Royals didn’t get “scraps” in return for Benintendi, but the Yankees did deal guys who they mostly dealt to clear space in the farm and save themselves from losing prized prospects in the Rule-5 Draft. The Yankees didn’t get an elite player by any means, but they get one with great on-base skills, and if he can find his power stroke in NY, he could be a great pickup. A 115-120 OPS+ bat is what I expect from him.



Grade: B+

Yankees Pick Up Scott Effross In a One-For-One

The Yankees losing Michael King changed everything. They needed a new stud reliever, and Jack Curry’s tweet about the Yankees getting Scott Effross stunned me. Scott Effross has posted elite numbers this year, posting a 2.66 ERA and 2.18 FIP alongside a 21.9% K-BB%. He’s done so in high leverage situations, ranking in the top 30 in Win Probability Added for relievers, and he’s got nasty stuff. His submarine arm slot creates for some disgusting movement that should fit in nicely with a Yankee bullpen that posses a plethora of guys with wicked stuff.

The Yankees traded a good prospect in RHP Hayden Wesneski for him, but Effross has 5.5 years of control remaining. This is a top 30 reliever with some incredible movement, and they’ll love throwing him into high leverage spots. He isn’t just a guy that can handle righties, with lefties posting an OPS below .500 against Effross and striking out 30% of the time against him.

Grade: A

Yankees Get an Ace and a Reclamation Project

The Yankees desperately needed to acquire an ace-caliber pitcher, and Frankie Montas perfectly fit that mold. He has good strikeout numbers, generates a ton of groundballs, and has wicked stuff. He’s got 1.5 years of control, and the Yankees are definitely going to be a formidable opponent with him and Cole anchoring the top of the rotation. Montas ranks 17th among 86 starters in fWAR since 2021 and 15th in strikeouts (minimum 200 IP). He’s. bonafide ace, and there’s room for him to improve with better pitch selection in New York with Matt Blake.

Also in the deal is RHP Lou Trivino, a reliever with great stuff but poor results. A high K% and high GB% should typically result in a low ERA, and yet his is over 6. On Fireside Yankees, we discussed how Lou Trivino could improve, and his four-seam fastball usage being cut down dramatically is an easy way to see that happening.

In return, the Yankees traded LHP Ken Waldichuk, LHP JP Sears, RHP Luis Medina, and 2B Cooper Bowman. Waldichuk and Medina were top 10 prospects in the Yankees’ farm system, but ultimately this haul seems underwhelming for Oakland in comparison for what the Reds got for Luis Castillo. The Yankees preserve their best position player prospects and have the requisite pitching talent in their last two drafts to start replenishing the mass exodus of arms in the farm.

Grade: A+

Yankees Dump Joey Gallo

The Yankees trade Joey Gallo to the Dodgers and, in return, get Clayton Beeter. Beeter is a wild-card arm with great velocity but horrible command and a HR problem. If he can get his mechanics down, he could definitely be a great starter, but reality is that he’s probably a reliever at the next level. He’s a 45 FV prospect with multiple 60-grade pitches, but he is Rule-5 eligible soon, and so that will be a task for the Yankees to figure out eventually.

The Yankee originally acquired Joey Gallo for a big haul, but it didn’t pan out. His OPS+ plummeted in NY to below a 90 when he was around a 115-120 in Texas. A disappointing outcome for Gallo and the Yankees and an example of good process but bad results. The Yankees needed left-handed power, and Gallo just didn’t bring the power he was expected to have. I’ll reserve the A’s for moves that clearly made this team better and give a modest grade for getting a good return back for a struggling slugger.

Grade: B

The Stunner That Brings In Speedy Center Fielder

As if the deadline was not already hectic enough, the Yankees and Cardinals make arguably the least expected trade of the day. The Yankees traded LHP Jordan Montgomery to the Cardinals and, in return got CF Harrison Bader. Harrison Bader most likely won’t return until late August or early September, but his impact in October will certainly be felt. Aaron Hicks has started to struggle again, and Bader provides a clear upgrade in CF in all aspects. He’s a ~105 OPS+ bat with elite speed and is arguably the best defensive CF in the sport. I wonder how he’ll adjust to NY, but seeing that he grew up in NY and isn’t going to be asked to be a star-caliber player, I think he’ll do nicely here.

Losing Jordan Montgomery absolutely hurts. The pain of losing a long-time Yankee added onto the fact that now Domingo German will regularly start until Luis Severino returns in September. This isn’t a move for August, rather for October, but it still is a risk. If anything goes wrong, Jameson Taillon getting the ball in Game 4. Cashman is really taking a huge risk trying to improve the roster.



Grade: B-

The Yankees overall deadline is an A. They’ve gotten a lot better in a lot of different way and are primed to make a title run. We’ll see if this is truly their year, but a lineup that loaded with their pitching should do pretty nicely.