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Yankees GM Brian Cashman's Biggest Mistake

Yankees General Manager Brian Cashman is one of the great GMs of any team at any time. Even legends are imperfect, however. So while it’s easy to forgive someone who’s done so much for the team, one mistake is as unforgivable as it is unfathomable.


Yankees Stadium still waiting for banner 28


Yankees General Manager Brian Cashman will go down in team history as perhaps the greatest GM the team has ever had. He’s made a lot of great moves over the years and guided the Yanks to being a perpetual playoff team.


Despite the title of the article, I’m a fan. But one of his decisions has hamstrung the team for years, likely preventing them from already making it to, if not winning, the World Series.


That’s a bit too big to overlook.


But before I reveal his biggest mistake, and to keep the suspense going, I’m going to take a moment to discuss his second-biggest blunder.


I’m Not a Number


Cash seems to think that the players are merely a series of numbers. He’s wrong about that. Every year there are teams built to win it all. The Yankees might be one of them more often than most, but they are never the only team.


To compete against those other teams–the Astros, Braves, Dodgers, et al–takes more than just looking up their stats on Baseball America.


It takes guts and courage.


It takes walking out there on the field every day feeling like you’d rather die than lose that day’s game.


You have to give everything you have to beat those other teams. If you’re not willing to work harder than everybody else, then somebody’s outworking you. And they’re going to win.


That’s why it’s imperative to make sure everybody Cashman puts on the team gives maximum effort every day. But even that’s not enough. You’ve got to have someone with a bit of the red-ass, someone who’ll get in the other players’ faces when they don’t play the game the right way.


Which brings us to Gary Sanchez and Gleyber Torres.


I was a big fan of Gary’s when he arrived, even though I knew of his disciplinary problem from his time at Double-A. That excitement only grew when he spent his rookie campaign looking like the second coming of Babe Ruth.


Soon enough, however, he made it clear that doing everything in his prodigious power to propel the Yankees to their next title just wasn’t in his DNA. It’s why he’s no longer on the team and why he’s struggling to stay in baseball.


But he shouldn’t have been a Yankee as long as he was. I remember the game where he failed to tag out a runner coming home who should have been out by ten feet. But Gary was just too nonchalant to make the play. Winning was not important enough for him to simply bend down.


That’s inexcusable.


First, he should have never been allowed to stay on the team long enough to make such a lazy play. Second, he should have been traded before the first pitch was thrown the next day. I won’t mythologize George Steinbrenner, but one thing he knew for sure was that kind of play infects the clubhouse and ruins championship teams.


The Boss would have traded him in the middle of the game. And he would have been right to do so.


How can the manager or team leaders expect the rookies and free agents to try their hardest when one of the untouchable Baby Bombers plays like that? A player like that is a poison in the clubhouse.


A player like that has to go, now.


But that’s not what Cashman did. He kept him on the team for years after he should have been gone because all he could see was the back of his rookie baseball card.


Arrested Development


How did he think that would affect the development of someone like Gleyber Torres?


My guess is he didn't think about it at all. More’s the pity as Torres came up needing guidance on playing the game hard and smart. He needed to be around guys who showed up every day with a fire in their belly and a burning desire to win.


Playing alongside Sanchez did not help. Instead, it led to Gleyber thinking dogging it is fine at the major league level. It’s hard to say how much this impacted Gleyber’s development, but we do know he still struggles with those same issues today.


Which is why Torres should have been traded two years ago.


He has not until recently shown the desire and drive to win at all costs. He’s been showing that a lot more lately, but that doesn’t help the 2021 Yankees or the 2022 Yankees.


I’m not sure anyone can help the 2023 Yankees.


Why the Yankees Keep Losing to the Astros


But it goes beyond that. Every clubhouse needs a player who holds everyone else accountable for not playing at a championship level.


We all know what Kirk Gibson did for Destiny’s Dodgers. That great Yankees dynasty had a locker room full of intense players. And they had Jorge Posada, who would put guys up against a locker if they played below the Yankees level.


It’s why the Astros have been the best team in the American League over the last few years. The cheating, scumbag Astros.


Every team wants to knock them out of the playoffs for what they did. Yet they just keep on winning and making it to the World Series. Why? Because they’ve got Alex Bregman. That guy looks pissed all the time. He looks like he’d fight you under the stands for not turning a difficult double play.


I don’t know anything about the Astros, except that they’re a bunch of cheating scumbags. But my guess is he drives that team with his fiery approach to the game.


Where is that guy for the Yankees? Aaron Judge is as passionate about winning as any player in the game. But he can’t put a guy up against a locker. He’s huge. If he did that, he’d come off like a bully.


Giancarlo Stanton, too, I’m sure, wants to win as badly as anybody. But his mellow Southern California vibe–and propensity for watching his non-home runs bounce back into the field of play instead of running out of the box–disqualifies him from that role.


The Yankees simply don’t have that guy. And it’s hurt them.


That’s on Brian Cashman.


Yankees GM Brian Cashman's Biggest Mistake


That brings us to an even bigger mistake than that one: replacing Joe Girardi with Aaron Boone.


We’ve got several years of data now and I can’t help but notice that Girardi got more out of his players and the team. This isn’t just speculation. For instance, the aforementioned Gary Sanchez had his best years under Girardi. In 2016, Sanchez slashed .299/.376/.657, then followed that up by hitting .278/.345/.531 in 2017.


He also hit 53 homers over those two years.


Then Girardi was fired at the end of 2017, and Sanchez went steadily downhill after.


He fell hard and fast to .186/.291/.406 in 2018, then posted a slash of .232/.316/.525 the following year. In 2020, he hit just .147/.253/.365. And while he did hit 34 home runs in 2019, his home run totals for 2018, ‘20, and ‘21 were just 18, 10, and 23.


That is not the next Babe Ruth.


More importantly, his focus and effort regressed under Boonie.


Proof of Concept


An additional example in the difference between the two managers comes from Michael Kay. Every year the Kayster would show how many wins the Yankees were projected to have. And he’d also show how every year, Girardi led his teams to surpassing those expectations.


Every year.


I notice Kay doesn’t bring that up anymore. That’s likely because Boonie is getting less from his players, not more.


Yet Yankees fans everywhere remember how Girardi’s tenure ended. The Baby Bombers unexpectedly took the eventual champions and scumbag cheater Astros to game seven of the 2017 ALCS. Whether they would have won that series had the Astros not cheated, we’ll never know.


But we do know they haven’t been as close since. In fact, they’ve gotten worse every year, even though the roster has gotten better.


They lost to the hated Red Sox in the ALDS the following year. And even though they made it back to the ALCS in 2019 against the Astros, the series didn’t seem nearly as competitive as the Yankees lost in six.


2020 saw them lose to the Rays in the ALCS, while they regressed all the way to losing the Wild Card game in 2021 once again to the Red Sox.


Last year might have been the biggest disappointment of all. Here's how ESPN summed up the start of the Yankees season:


The Bronx Bombers are absolutely dominating the opposition this season, as they've reached 50 wins in 67 games for a winning percentage of .746. It puts them in a class of their own in MLB this season -- the next closest squad, the New York Mets, are six games behind. The Yankees have a commanding lead in the AL East and they're pretty obviously the team to beat in the postseason.

Except they weren't. This all-time Yankees team got shut out in the ALCS by the Astros in a feeble effort by the Bombers. This year, they might actually miss the playoffs altogether.


Girardi’s Yankees were hungry and tough and played with an edge. Boonies boys go down without a fight.


That’s also on Brian Cashman.


Playing by the Book


What makes it so perplexing is that Cash loves statistics. But that’s exactly how Girardi got so much out of his teams. He used his dozens of notebooks to see how to put each player in exactly the right position to maximize his chances of success. That seems like a good thing.


But apparently, getting the most out of the players and guiding them to premature playoff success just wasn’t good enough for Cashman. Yeah, who wants that?


Instead, he decided that the team needed a buddy. Giradi's biggest sin was he didn't hang out with the players and didn't play video games with them. In fact, the only test Cashman gave to his candidates was handing them the statistics of the players and seeing who could construct a lineup the way he and his executives would do it.


That’s not a manager; that’s a puppet.


But Cash got exactly what he wanted. Aaron Boone hangs out with the boys and plays video games with them. He never criticizes them as that might hurt their feelings. And he never pulls them from a game when they dog it or benches them for poor play. God forbid.


I’m sure that makes everyone from Gleyber to Cashman feel just dandy. But it hasn’t helped them hang banner number 28, has it?


Don’t get me wrong: that type of manager is fine if the players are putting the pressure on themselves. If the players are truly policing the clubhouse. But it’s not okay when your superstar brings his Opie Taylor, aw-shucks attitude through the door. Or when your other supposed superstar, Stanton, lets doubles turn into singles while he watches from home plate.


That kind of team needs someone to get pissed off when they underperform. They need someone to hold them accountable.


And since it’s definitely not going to come from laid-back Hal Steinbrenner or iceman Brian Cashman, it needs to come from their manager.


That’s never going to happen. Not when the manager is too busy being a buddy to put pressure on the players.


The Incredible Shrinking Yankees


The results are clear to see. The Yankees currently sit at 50-45 and the bottom of the AL East. Even the Red Sox are above them, and there is no comparison between the two rosters. They also sit 2.5 games out of the Wild Card, again below the Red Sox.


I’m not saying the Yankees can’t win a world championship with Boonie as the manager. There’s still time to make their way into the playoffs. I’m just saying they’ll have to do it in spite of Aaron Boone, or at least coincidental to him.


And they’re sure not going to be a dynasty.


It comes down to one simple fact. In sports (and gambling), you never mess with success. That’s especially true in the superstitious world of baseball. This is a sport filled with guys who, if they put on a pair of new underwear and win that day, might not change their underwear again until they lose. It’s why Wade Boggs ate chicken before every game, which is far less gross than the underwear example.


Well, Girardi was successful. He’d already led one squad, the 2009 Yankees, to the promised land. But Cashman fired him anyway, infuriating Yankees fans and the baseball gods. Then he doubled down on that error by hiring Aaron Boone.


That is Yankees GM Brian Cashman's Biggest Mistake. And it’s one the Yankees and their fans have been paying for ever since.


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