Re-grading Yankees' 2022 trade deadline: What went so very wrong?

Captain Hindsight, reporting for duty.

Obviously, in the light of day, many of the Yankees' 2022 trade deadline deals look different than they did at the moment of execution. My knee-jerk feelings on all of these trades was well-documented with our instant reaction last summer; and no, I'm not just linking this because I gave theFrankie Montas deal a "B+" and worried about his shoulder.

A lot of the way we now view the 2022 trade deadline shifted this offseason, and not just because of the announcement of Montas' surgery. In all, the shuffling looks a lot more profound if Andrew Benintendi comes back to finish the job this offseason rather than accepting a freaky high offer with the Chicago White Sox (best of luck!).

Things had, of course, already changed when Benintendi was taken out of the Yankees' playoff run, where he was supposed to play the role of "Astros Killer". They changed when Scott Effross was ruled out for last season and the 2023 campaign, just before the playoff roster was announced. And yes, they changed when Montas showed up with a busted wing and was never able to fix it.

The 2022 trade deadline instant grade was optimistic for a reason. The Yankees surrendered very little for Benintendi. They gave more for Montas and Effross and, in doing so, patched up their three biggest deficiencies. Unfortunately, they didn't receive more than a month's worth of patches. No matter what the pitching prospects surrendered ultimately amount to, it's hard to look back at this deadline with even a semblance of the joy we felt in the moment.

You know, the moment before Jordan Montgomery was traded, which wrecked the deadline ... but also somehow got the Yankees the best asset they accrued in any deal last year? We're tired. It's tiring. Let's do it.

Re-Grading the 2022 Yankees Trade Deadline (aka Grading Disasters on a Sliding Scale)

Grading Yankees' Andrew Benintendi Trade

Then: A-
Now: B

In perhaps the biggest Rage "What the Fffffff" of the 2022 season ... man, it is so incredibly frustrating how Benintendi's season ended.

Right when he was heating up. A month before he'd have a chance to cement himself as the Yankees' contact-forward missing piece in the postseason. Thanks to a fractured bone that he thought he'd had removed a decade prior. Just wonderful.

A five-year, $90 million for Benintendi, after his Yankees tenure, feels like an unreasonable ask. But it would've been so much fun to watch him, at his peak, become the latest Boston/New York crossover to bring a title to the Bronx. The trade package the Yankees surrendered here was surprisingly light; headliner Beck Way has begun 2023 with a 17.18 ERA.

All things considered, the only pain here was already suffered last September, but it continues to burn that the Yankees were robbed of seeing whether their plan was sound by a freak accident.

Grading Yankees' Frankie Montas/Lou Trivino Trade

Then: B+
Now: Generous D

The process of acquiring Frankie Montas, Frontline Starter, can be as "sound" as you'd like it to be, in your own personal vacuum. When the pitcher acquired self-reports that he was trying to pitch through a shoulder injury all of last summer, it's impossible to look back on this trade kindly.

It's tough to honestly believe that Brian Cashman and the team medical staff didn't do their due diligence last season when acquiring Montas, but ... in retrospect ... it's also tough to believe anything different.

The Yankees must not have seen anything structurally worrisome in Montas' MRIs. If they'd asked the man honestly, though, he would've told them he didn't feel right. Maybe they asked him. Maybe they went through with the trade anyway. Maybe they found Ken Waldichuk/JP Sears/Luis Medina a small price to pay, and decided the risk was worth the reward, even as the odds of the reward coming to fruition shrank every time Montas picked up a baseball and felt "not 100%".

We didn't receive the documents clearing Montas last summer, but we believe the pitcher. He wasn't right. He didn't shake it off. And this never should've happened. Cashman has not picked the right high-profile starter in a long, long time. Please don't ask me about Carlos Rodón.

Lou Trivino is alright. He's also injured.

Grading Yankees' Joey Gallo Trade to Dodgers

Then: A+
Now: A+++

Joey Gallo had a viscerally unpleasant Yankees tenure made all the more gruesome by the fact that he was so easy to root for. Childhood Yankee fandom. Titanic power. Underrated defense. All-Star pedigree.

None of it ever showed up.

Dealing two months of Gallo for a warm body of any kind, after his .160 average with 88 strikeouts in 58 games (93 OPS+) somehow got worse in Year 2 (.159 average, 77 OPS+, 106 strikeouts, 82 games), would've been a victory. Now that we know he also fizzled out in Dodger Blue, and resulted in the Yankees adding a top-15 prospect in Clayton Beeter to their system, this goes from a "sure, why not" to an "absolutely, yes, thank you, can we do this again?".

Beeter might be a reliever long-term, but so far, so very good; he's struck out 14 men in 11 innings at Double-A Somerset. His ERA is 0.82.

Gallo has been great so far in the Twin Cities. That is fantastic. His inability to click in the Bronx might have involved the most painful performance anxiety we've seen in this era of modern Yankees baseball. But any way you slice it, this trade is a tremendous Cashman victory (and a bizarre Andrew Friedman oversight), just like it was last year.

Grading Yankees' Harrison Bader/Jordan Montgomery Trade

Then: D
Now: B+ Pending Bader Extension, and a Win-Win

The low grade on this trade was wholly deserved at the time. Sacrificing pitching depth, willingly, for a team that needed more pitching and is historically injured, was a wild gamble. Fittingly, the Yankees lost Montas and Nestor Cortes Jr. soon after, with Luis Severino still on the shelf. All this, and the man they acquired in return was injured and out 'til September? D might've been kind. Oh, and the chemistry killing! This also killed team morale. Right.

But ... lost in the anger cycle was the fact that we know Jordan Montgomery. We know he is a mid-tier starting pitcher with relatively low annual ERAs, relatively low swing-and-miss, and relatively low trust levels entering a postseason series. Montgomery would be helping the Yankees eat innings right now. He would also occasionally be allowing seven runs in an inning, as he did to the upstart Diamondbacks earlier this week. He is a fine pitcher who plays up in the NL Central -- and, it should be mentioned, lasted only 2.2 innings and walked 3 in last year's postseason.

Bader? He became a Yankees postseason legend last October when he drilled three home runs against Cleveland and two against Houston. He embodied what New York City still believes itself to be: hard work. speed, and a little bit of deserved flash.

If you'd asked me to reevaluate this trade in March, I would've enthusiastically bumped it a tick or two. Now that the oft-injured Bader is rehabbing again, I'm less bullish on the obvious win (especially since the Yankees' rotation is still hurting).

You know, when an executive or writer attempts to evaluate a win-win deal and calls it a "good baseball trade"? Think Luis Arraez for Pablo López. Sure, it hurts to lose either player, but need-for-need ... it turns out alright.

Trading Montgomery for Bader was a bad baseball trade. The Yankees needed reliable starting pitching. They still do. The Cardinals had too many outfielders. They still do. They were happy to pawn Bader off on the Yanks.

And yet ... win-win. Pretty safe win-win. Talk about bad process leading to unexpected results.

BONUS: Grading Yankees' Gleyber Torres/Pablo Lopez Non-Trade

My brain ... is on fire ...

It's almost impossible to imagine these current Yankees sustaining their pace without Gleyber Torres, who's contributed quite a bit thus far, matching Rickey Henderson's exploits. The 2023 rotation looks a lot better with Pablo López ... but the 2022 rotation doesn't improve tremendously with his addition (4.61 ERA in Aug. 2022, 5.33 in Sept. 2022) ...

... But that's irrelevant, because he wouldn't have faced the same teams ... but maybe he never perfects the sweeper and ticks up his velocity this offseason if he comes to the Yankees ... but he probably does, considering he arrived in Minnesota fully evolved ... you know what? Ugh. We would've given this a C+ last year, and would have to bump it up to a B this season, knowing what we know about the Yankees' rotation.

Would they have extended López like the Twins did, though? Would they have let Carlos Rodón go elsewhere, in order to do so? It's tough, but give us a healthy Rodón (someday ...) and Torres over Lopez. Brutal call to have to make in the Metaverse, though.