Grading Yankees' transformative 2022 MLB trade deadline moves

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Every New York Yankees fan’s fear was that the 2022 MLB trade deadline would pass with a whimper, as teams like the Padres, Dodgers and Mets reloaded for the stretch run. In reality, though, you had to know the Bombers wouldn’t intentionally close a championship window.

After all, 2021’s deadline featured a pair of Brian Cashman splashes in Joey Gallo and Anthony Rizzo. That team wasn’t a finished product. It was a borderline playoff contender that needed a midseason overhaul to get over the hump — and barely made it, at that. This year’s roster was different. The 2022 Yankees were an obvious contender beginning to show wear-and-tear after starting at a record-setting pace. And Cashman did not rest on his laurels, even after being outbid for his main pitching target.

Though Luis Castillo will not be pitching in the Bronx — except on Wednesday, f@&* — the Yankees wound down the deadline by acquiring Frankie Montas, relievers Lou Trivino and Scott Effross, and Royals outfielder Andrew Benintendi, as well as dealing Joey Gallo (but you knew that weeks ago) and Jordan Montgomery (which has left a simmering pile of embers, even hours later).

There’s no Juan Soto in that pile, but plenty of additions to the framework, and the Yankees are a more complete team now than they were post-Subway Series.

In order to add core pieces, New York surrendered several upper-level pitching prospects from a system that practically breeds them at this point. Hayden Wesneski, Ken Waldichuk, Luis Medina and JP Sears are gone, soon to be replaced by Will Warren, Matt Sauer, and a number of other fast-risers. You have to give to get, and the Yankees didn’t escape unscathed. They did, however, manage to hang onto Anthony Volpe, Jasson Dominguez, Austin Wells, Trey Sweeney, and — most shockingly — Oswald Peraza.

Will all those players factor into the Yankees’ on-field future, or some tremendous package to be formed later? This extremely active and somehow still non-seismic trade deadline deserves proper grading.

Grading New York Yankees’ 2022 MLB Trade Deadline haul

NEW YORK, NY – JULY 28: Andrew Benintendi #18 of the New York Yankees (Photo by Adam Hunger/Getty Images) /

Grading Yankees’ Andrew Benintendi Trade: A-

New York’s move for Benintendi gets docked a half-letter grade because the ex-Sox is a relatively powerless alternative to Ian Happ, who was also available, and Juan Soto, who was a pipe dream wrapped in a candy-coated rainbow.

That said, the Yankees obtained an All-Star who knows and loves the ballpark, and who can be counted on to pick up runners on base, whether through singles, doubles, well-placed grounders, or sacrifice flies. Benintendi is rented reliability.

He cost only Beck Way, an up-and-coming pitching prospect, T.J. Sikkema, a nasty lefty who’s barely pitched since being drafted and must be protected from this fall’s Rule 5, and Chandler Champlain, a Low-A relief option. Those three pitchers are various levels of intriguing, but you’d sacrifice any and all of them to add more bat-on-ball skills to a Yankees lineup that finished July atop all of baseball in terms of production, but still appeared to need a spark.

For a Yankees team that spent July mostly stuck in the mud and near-.500, you could do far worse than a battle-tested playoff “veteran” who’s still just 28 years old and plays exceptional defense. Benintendi hasn’t had his Signature Yankee Moment yet, but has been ol’ reliable in the interim. No complaints here.

Scott Effross #57 of the Chicago Cubs (Photo by Rich Schultz/Getty Images) /

Grading Yankees’ Scott Effross Trade: A

Without Michael King’s extremely tough-to-swallow injury, a Scott Effross trade likely doesn’t happen, based on the cost of its completion. Hayden Wesneski is a helium balloon right now, and the Yankees probably would not have pulled the trigger on a reliever with 5.5 years of control attached if they could still count on King.

A reliever this good who’ll be around for this long costs more than a rental like Mychal Givens or David Robertson, though, and the Yankees gave to get, silencing some mounting instability in the back end of their bullpen.

Most assumed the Yankees would try to swing a summer deal for “The Next Clay Holmes” — and they did, we’ll get to that shortly — but The Original Clay Holmes is hitting an unfortunate wall at the moment. Factor in recent slowly-but-surely progressions from Aroldis Chapman and Jonathan Loaisiga, and the complexion of the Yankees’ bullpen is about to shift once again midseason.

Effross has been special, the type of change-of-pace arm who could own the late innings in the Bronx with his sweeping slider and devastating cutter. In order to get 5.5 years of bullpen production, you need to surrender a top-10 pitching prospect on the verge of the big leagues, who brings a sweeping breaker of his own alongside a bulldog mentality.

Wesneski should be nails in Chicago, but Effross was needed now, and he’ll be needed next year, the year after, and three years from now. Luckily, he’ll still be under team control then.

Frankie Montas #47 of the Oakland Athletics (Photo by Lachlan Cunningham/Getty Images) /

Grading Yankees’ Frankie Montas Trade (And Don’t Sleep on Lou Trivino): B+

Forgive the conservative grade here, but Montas’ recently-barking shoulder looms large in the wake of Luis Severino hitting the 60-Day IL and returning in mid-September (at best). Montas has been excellent dating back to the start of 2021, finishing sixth in the Cy Young chase last season, and has very solid statistics against the Yankees’ main competition. 1.83 ERA in 19.2 innings against the Red Sox. 1.87 ERA in 33.2 against the Rays. 8-5, 3.40 ERA against the Astros. That’ll all play.

Somehow, the Yankees managed to acquire him without surrendering top shortstop Oswald Peraza, too, leaving the 22-year-old as a second-half option in the Bronx. Even so, Ken Waldichuk, Luis Medina and JP Sears is one hell of a big-league ready trio; even if Medina eventually transitions to the bullpen, he’s still a heat-chucking maniac.

Still … Brian Cashman has a “go for it” team and he is going for it. For too many years, he’s come up just short on Montas-level talents and beyond, seemingly scarred by Larry Rothschild’s unsuccessful tinkering with Sonny Gray. This time, he dealt some painful prospects away for a shot at a genuine No. 2 starter, whose import only increases with Luis Severino gone until mid-September.

Lou Trivino? Somehow, his BABIP is a ridiculous .451, meaning that any time anyone makes contact with his pitches — mostly on the ground — they bat nearly .500. That’s unsustainable and kooky beyond belief. Even if he doesn’t get back to the level he’s reached in previous years after Matt Blake streamlines his arsenal and places him in front of the Yankees’ superior infield defense, it’s still a worthwhile gamble, and a cherry on top of an impressive-but-not-perfect trade.

Joey Gallo #13 of the New York Yankees (Photo by Dustin Satloff/Getty Images) /

Grading Yankees’ Joey Gallo Trade to Dodgers: A+, Depressing Necessity

The New York Yankees would surely have loved to keep Joey Gallo, the 40-homer All-Star they obtained at the 2021 trade deadline.

Unfortunately, the team never had control of that player to begin with.

Instead, the Yankees’ version of Gallo was a tragic .160 hitter whose time in the Bronx ended right around when he began to give interviews about how he had very little interest in showing his face in the streets of New York City. The Yankees were his childhood team. Suddenly, they needed to find an out clause for a down-and-out slugger.

Unfortunately, Gallo will not get the chance to recover somewhere with dimmed lights; he heads to Los Angeles in exchange for Dodgers right-hander Clayton Beeter, a top pick from 2020 who’s struck out 88 men in 51.2 innings while walking 35. Still, he ranks 15th in MLB Pipeline’s Dodgers list, and is about as strong a prospect as New York could’ve hoped to receive here in a deal that the whole world knew was going down.

Gallo’s fate in the Bronx was the worst-case scenario. His average dropped 60 points from where it needed to be for his brand of baseball to translate, and in turn, some fans made harassment of the 28-year-old into their entire brand. A swap with Milwaukee or Atlanta felt ideal. A Dodgers trade? The Yankees prioritized the return over Gallo’s comfort. That’s the business, yet again.

Harrison Bader #48 of the St. Louis Cardinals (Photo by John Fisher/Getty Images) /

Yankees Trade Jordan Montgomery to Cardinals for Harrison Bader: D

The New York Yankees added Frankie Montas — legitimately Frankie Montas! — the Monday before the 2022 trade deadline. By the time Tuesday rolled around, their rotation was worse than the one Montas had joined the day prior.

Brian Cashman beat the buzzer by dealing Jordan Montgomery to the St. Louis Cardinals in exchange for defensive superstar center fielder Harrison Bader, who is unfortunately in a walking boot at the moment, and might be sporting one until the end of the season. He may come back in September. He may not. If he doesn’t, the Yankees receive a player to be named later for their No. 5 starter.

Many fans presumed this deal was completed as a precursor to Pablo Lopez or Carlos Rodón heading to the Bronx. It was not. Nothing followed.

Montgomery, a good-not-great left-hander who never got the requisite run support, had seen his ERA beef up to 3.69 recently. Regardless of whether or not he’d make an ideal playoff rotation (he wouldn’t), he’ll now give way to Domingo German every five days, a deplorable outcome.

The Yankees’ desired October rotation is Gerrit Cole, Frankie Montas, Luis Severino and Nestor Cortes Jr. Severino is currently on the 60-Day IL; by mid-September, we’ll know more about his lat. If a playoff-bound team only has four trustworthy starters (in August, with one on the shelf), that is not enough trustworthy starters.

Cashman has questions to answer about his motivations here. Otherwise, it seems the team is relying on absolutely zero depth beyond their four postseason arms, hoping nobody gets hurt in two months when one of the names in question is hurt already. Hopefully Bader gets back and shines as the team’s sixth outfielder, which is double the amount of outfielders that typically take the field at any given time.

NEW YORK, NEW YORK - SEPTEMBER 10: Aaron Judge #99 of the New York Yankees in action against the New York Mets at Citi Field on September 10, 2021 in New York City. New York Mets defeated the New York Yankees 10-3. (Photo by Mike Stobe/Getty Images)

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Grading Yankees’ transformative 2022 MLB trade deadline moves