Typically, the subjective assessment of a GM's trade deadline ends up somewhere in between, as faint praise mixed with cautious optimism. If someone "goes for it" -- especially someone with a reputation for success -- it's often hard to fault them ... until the pieces come clattering down. If someone decides to play things safe -- again, if they have pedigree -- most of the discourse backs their direction until we're given the benefit of hindsight.
Yankees GM Brian Cashman, who sits on his hands about as often as he chooses the correct pieces in free agency and trade talks (rarely), has certainly earned that benefit of the doubt from those who cover his maneuvers. For as long as Hal Steinbrenner has smiled and nodded in his direction, there's been a sort of silent agreement that, yes, while things may look fuzzy now, Cashman ultimately knows what he is doing. The criticism for, say, Billy Eppler of the Mets or Sandy Alderson of the Mets or [INSERT NAME HERE] of the Mets has always been louder in the mainstream.
Until Tuesday, when Cashman looked at a flawed roster, determined that said flawed roster was "still in this," then proceeded not to supplement it accordingly in any way. Whether you believe in this group of Yankees or not, what he chose to do was objectively wrong. You think this group's a dud? Sell. You think it's a winner? Buy. You claim it's a winner, and you don't buy? You, my friend, have failed.
This time around, Cashman wasn't quite so teflon in the aftermath, as he spewed platitudes about how the group was obviously "in it to win it" but couldn't add a left fielder today, yesterday, or in either of the past two offseasons because of that goshdarn budget. Media veterans like Jon Heyman and Joel Sherman openly skewered him, with Sherman's Wednesday morning column taking a battleaxe to Cashman's past several seasons, if not the entire post-2017 era. The Athletic's Chris Kirschner and Brendan Kuty, access be damned, both awarded him with "F" grades for Tuesday's efforts, treating him like the negligent steward he's been for several seasons now.
If the tide was about to turn and make things toxic enough for Steinbrenner to take note of his investment cheapening, it would look a lot like this.
Yankees GM Brian Cashman needs to answer for years of failure ... according to New York sportswriters! Alright! We're getting somewhere!
In the late '90s, Cashman was the steward of a team that someone else had built, and built extremely well. In the mid-2000s, he splurged on offensive star after offensive star, building a ridiculously deep lineup that somehow didn't work at all come October (and was never paired with a pitching staff of any kind). In 2005, they got outgunned by the Angels, as Randy Johnson faltered spectacularly. In 2006, Kenny Rogers and the Tigers effortlessly dismissed them. In 2007, Cleveland did the same.
That led directly to Cashman's one success story: the 2009 World Champions, a team absolutely covered in lefty bats and switch-hitters. Even that team didn't have a rotation, though; an expensive three-man unit carried them to the finish line in George's "budget be damned" farewell season.
Since then, it's been more of the same offensively. Regular season juggernaut, postsason also ran. 20 years after he was first tasked with trying to create a competent playoff offense, he still refuses to deviate from his unworkable blueprint.
Or take it from Sherman himself, someone who might just have the chance to turn this thing around with his acidic pen:
"It would take a book to delve deeply into how the second-highest-paid team was hitting .230, was 21st in runs per game and counted journeyman strikeout artist Jake Bauers as their most impactful hitter not named Judge.- Joel Sherman
But there are drafts that have not netted even enough average bats. There is an international market that has not brought a Juan Soto or Ronald Acuna Jr. or Wander Franco. There was the plummet of Greg Bird, Gary Sanchez, Miguel Andujar and Clint Frazier — and holding onto them way beyond their expired warranty.
There was unrelenting arrogance to stay overly right-handed and disregard strikeouts even as one postseason after another exposed it as a failed philosophy; plus left them lacking diversity and athleticism when that is needed more than ever."
The Yankees failed on Tuesday. Of course they did.
But it takes more fortitude to note that not only did they fail spectacularly at threading the deadline needle this week, but they also failed in 2022. And in 2021. And certainly in 2020. Don't forget 2019, when the rocket ball gave them a unique chance to topple the Astros, but they sat silently at the trade deadline as their injured core yearned for supplementing. They failed in 2018, adding right-handed anchor Giancarlo Stanton after he "fell into their lap" for a reason. They've failed Aaron Judge since the day he debuted.
But let's say it one more time, loud and clear: the nebulous "Yankees" didn't fail. Brian Cashman failed. And you're beginning to see that sentence written more and more often by people who really, truly matter. Maybe it'll help. Nothing else has so far.