Regrading Every Trade Deadline Deal the Yankees Made This Season

From a Frankie Montas blockbuster to the Harrison Bader head-scratcher, here's our updated grades on New York's five trade deadline deals.

When the Yankees made five different moves at this year's trade deadline, bolstering the big-league club with several impact players, New York received rave reviews. 

Sure, one trade was notably a head-scratcher, one star got away and another move never came to fruition, but overall, it was hard to criticize the Yankees when the dust settled on August 2. 

At the time, New York was the best club in the American League, a team with a 12-game cushion in their division riding a 109-win pace. 

General manager Brian Cashman made it clear that he wasn't satisfied with a hot start to the regular season. This club invested a significant chunk of their pitching depth in the farm system to give the organization a better shot to win the World Series this year. 

In hindsight, while some moves turned out to be tremendous for New York, others haven't panned out as the Yankees would've hoped. 

Let's take a look back at each of those five trades, regrading the deals now that the regular season has come to a close.

Regrading Every Trade the Yankees Made at This Year's Deadline

From the Joey Gallo trade to moves for Frankie Montas, Scott Effross and Harrison Bader, here are upgraded grades on each trade deadline move the Yankees made after the conclusion of the regular season.

Yankees Acquire Andrew Benintendi

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Yankees get: OF Andrew Benintendi

Royals get: RHP Chandler Champlain, LHP T.J. Sikkema, RHP Beck Way

Grade: B

Adding Andrew Benintendi to the mix was New York's first trade leading up to the deadline, a tone-setting move to show that this club wasn't messing around.

Benintendi started slow, but eventually found his rhythm. After going 2-for-25 to begin his Yankees career, the sweet-swinging outfielder slashed .296/.337/.466 from August 7 to August 31. The Yankees went 9-14 in that span, but it wasn't Benintendi's fault—their record could've been much worse if it wasn't for his boost in production.

Unfortunately, Benintendi would only appear in one more regular season game after that stretch. The 28-year-old broke the hook of his hamate bone in his right wrist on a swing and miss in Tampa Bay on September 1 and hasn't played since.

There's still a chance Benintendi can play a role in October, but the fluke injury casts a shadow on this trade. Considering the lefty is a rental, you want to get as much out of Benintendi as possible before the end of the year. If he's not able to play again in the postseason (or struggles in his return), this grade will sink even lower.

Plus, if it wasn't for the emergence of Oswaldo Cabrera, Benintendi's injury would've left a gaping hole in left field. Aaron Hicks has turned his season around over the last few weeks, but still, that's far from ideal considering the alternative. 

This is one of those trades that could age poorly depending on how the pitching prospects develop down the road. Then again, New York has been churning out high-quality arms in recent years. With all due respect to those three pitchers, they were expendable to go out and try to win a championship this season.

Yankees Acquire Frankie Montas, Lou Trivino

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Yankees get: RHP Frankie Montas, RHP Lou Trivino

Athletics get: LHP JP Sears, LHP Ken Waldichuk, RHP Luis Medina, 2B Cooper Bowman

Grade: C-

Without the inclusion of reliever Lou Trivino, this trade would be an F for the Yankees.

Frankie Montas was acquired to be a No. 2 in their starting rotation, an ace-caliber arm that was one of the most coveted starters available at this year's deadline. He didn't live up to expectations at all in pinstripes and ended up back on the injured list, dealing with an injury that the Yankees knew about before the trade took place.

Montas posted a 6.35 ERA in eight starts after the six-player swap. He allowed four-plus earned runs in five of those eight outings. The Yankees won just three games when he was on the mound.

Again, to make matters worse, Montas ended the year on the 15-day injured list with shoulder inflammation, the exact same issue that he dealt with earlier in the summer with the Athletics. He's unlikely to play in the American League Division Series and quite frankly, it's hard to justify him earning a roster spot even if he was healthy.

That was an injury Montas and the Yankees shrugged off as the trade went through, a deal that included three of the Yankees' best pitching prospects—Waldichuk was New York's No. 1 pitching prospect and Sears had been helping out in the big leagues already.

At least Trivino has been solid in the bullpen, a much-needed reinforcement. The right-handed reliever allowed just four earned runs in 21.2 innings pitched with the Yankees (1.66 ERA) over the final two months of the regular season. He's poised to play a key role in the playoffs since he has plenty of high-leverage experience from his years with Oakland.

Montas has one more year of control, so he has a chance to win over Yankees fans next season. Trivino has two more seasons remaining on his current deal.

Yankees Acquire Scott Effross

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Yankees get: RHP Scott Effross

Cubs get: RHP Hayden Wesneski

Grade: A-

Where would the Yankees be entering the postseason without Scott Effross?

Effross closed two games for New York after returning from the injured list in September. Overall, he allowed just three earned runs since he was acquired by the Yankees and all three came on one swing (a three-run home run off the bat of Cardinals shortstop Paul DeJong on August 7).

The sidearm reliever wasn't a big name by any means at the time of the trade, but now he's one of the most important arms in the Yankees' bullpen leading up to the ALDS, up there with Trivino and Jonathan Loáisiga.

This appears to be a deal that benefits both sides as well. Wesneski was another highly-touted starter in New York's farm system, a right-hander that was poised to make his debut with the Yankees by the end of this season. He's already shown what he can do at the big-league level with Chicago, posting a 2.18 ERA in six appearances (although five of those six outings came against teams that didn't make the playoffs).

If Wesneski turns out to be a top-shelf starter, we'll look at this deal differently down the road, but the beauty of adding Effross is that he'll be around for a long time. The funky rookie reliever won't be a free agent until after the 2027 season. That's five more years of control in the bullpen.

Yankees Trade Joey Gallo

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Yankees get: RHP Clayton Beeter

Dodgers get: OF Joey Gallo

Grade: A

With the way Gallo's tenure in pinstripes went, New York could've traded the struggling slugger for a box of scraps and benefitted from the deal. In this case, they got a talented right-hander back from Los Angeles.

Clayton Beeter, New York's new No. 9 prospect (per MLB.com), pitched to the tune of a 2.13 ERA in seven starts with Double-A Somerset after the Gallo trade, a dramatic improvement from his numbers with Double-A Tulsa in the Dodgers' system to start the 2022 season (5.75 ERA in 18 outings).

Beeter will need to show next year in his first full season in the Yankees' system that he's for real. Getting a pitcher with some upside back makes the whole Gallo saga an easier pill to swallow. Still, Yankees fans won't forget how poorly that trade worked out for New York at last year's trade deadline. Many of the prospects New York used to acquire Gallo from the Rangers are already in the Majors, flashing their potential for Texas.

Gallo finished the year hitting .162/.277/.393 for the Dodgers with seven homers and a 41.6 strikeout percentage in 44 games. He began this season batting .159/.282/.339 with 12 home runs and a 38.8 strikeout percentage in 82 games with New York. 

In other words, even with a complete change of scenery, Gallo has been virtually the same player in a different uniform.

Yankees Acquire Harrison Bader, Trade Jordan Montgomery

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Yankees get: CF Harrison Bader

Cardinals get: LHP Jordan Montgomery

Grade: A-

When this deal went through, at the buzzer before the deadline, there was an uproar among Yankees fans. Why trade a consistent, homegrown starter for an injured outfielder?

Even if Jordan Montgomery went on to pitch well for the Cardinals, helping to lead them to a division title, Harrison Bader has had an immediate impact with New York since returning from plantar fasciitis.

Bader's offensive numbers are far from scintillating—.217/.245/.283 in 14 games—but he's come up with some clutch, run-scoring hits and swiped a few bags as well. His defense is elite, both in the advanced numbers and in the eye test. Having him in center field for the postseason and for all of next year is worth the price of admission. 

Looking back, while it was a shocker to subtract Montgomery, think about how he would fit in this team's pitching staff entering the postseason. With Gerrit Cole, Nestor Cortes and Luis Severino in the rotation (with Jameson Taillon and Domingo Germán both ready to start games if needed as well), Montgomery would either be in the bullpen or left off completely.

The Montgomery deal was a shock to the clubhouse, a reminder that this sport is a business, but it's a move that's paying off when games matter most.

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