Yankees: At what point are we allowed to get mad at Brian Cashman?

The Mets and Padres have made blockbuster trades. The Yankees have done … nothing.

For years, general manager Brian Cashman has been the gold standard for front office executives across Major League Baseball. He’s been running the show for the New York Yankees since 1998 and has four World Series to show for it. He’s the longest tenured general manager in baseball.

However, one could say the glory days are long gone.

Three of those championships came from 1998-2000 and, not to be harsh, but the team’s infrastructure was already in place thanks to Gene Michael and Bob Watson. Make no mistake about it, Cashman orchestrated a number of moves to bolster those squads, but it’s not like he built those clubs from scratch.

That’s been his journey ever since the team missed the playoffs in back-to-back seasons in 2013 and 2014. That’s when all of their star players started to decline or leave in free agency. The last of the dynasty figures were officially on the way out. That’s when the real challenge started.

We’re not sitting here saying Cashman’s done a bad job since then, but it just simply hasn’t been enough based on the annual expectations for the organization. And after we’ve watched the San Diego Padres and New York Mets make massive splashes this offseason, we’re continuing to ask ourselves questions.

Cashman’s been an active GM who’s at the forefront of everything, that’s why he’s lasted this long. He’s built a new, contending Yankees team from scratch. He’s moving in stride with advanced analytics. He still makes the needed big free agent signings. He’s a trade wizard. But at some point, you simply have to go for it all. Cashman has largely been a reactive GM in recent years rather than a proactive one.

We’re done hearing about the Yankees’ lost profits. The entire world lost profits. Everyday Americans can’t make ends meet. Meanwhile, a team worth $5 billion is terrified of eclipsing a luxury tax threshold that will cost them a few million. On the flip side, we can understand not being hasty in free agency at the moment. The market is undefined and there’s no sense in the Yankees throwing money around when they have nothing to base it off of.

But there’s something to be said about being passive in a buyer’s market, especially via trades. Cashman notoriously loves to make deals, but he’s never that aggressive. You could point to the Giancarlo Stanton trade a couple of years back, but that wasn’t a case of emptying the farm system to address an immediate area of need in order to contend. They didn’t give up a whole lot because they were inheriting a mammoth contract … and, sorry to say it, but the acquisition featured a redundant player. The Yankees didn’t really need Stanton.

You could point to the Sonny Gray trade too. But 1) that didn’t work out for the Yankees and 2) that was one of those instances in which Cashman was trying to capitalize in Gray’s declining value. Why can’t we just get someone at their peak, pay a premium, and move on?

The Yankees need pitching, and they still don’t have it. Gerrit Cole is a great start in that department, but if the Houston Astros couldn’t win the World Series with him and Justin Verlander atop the rotation, how can the Bombers expect to do that without a No. 2 … or No. 3 … or No. 4 starter? We have no idea what the cast of arms behind him are capable of heading into 2021. We have no idea if DJ LeMahieu will be back. Even worse? We have no idea what the potential backup plans are. Many feel we still need one for Gary Sanchez! There are a lot of issues! There are zero solutions! The season’s been over for nearly three months.

So we ask, when can we start expressing frustration with our highly-esteemed general manager? It feels wrong, but where else do we go? We can yell about Hal Steinbrenner all we want, but the Yankees owner isn’t stopping Cashman from emptying a portion of the farm system to acquire a guy like Luis Castillo to fortify the rotation. It always feels like the Yankees are waiting to strike when the moment’s right, but that’s not how it always works. You need to create your own opportunities instead of getting shepherded around by market value and all that nonsense. Overpay for once!

We hate to say it, but we need a little Dave Dombrowski aggression. No regard for the future 3-5 years from now. The Yankees’ premier window is 2021 and 2022. It’s a sin to even draw that parallel, but why are we waiting to make the most shrewd move possible? It can’t incessantly be about getting every single detail of the deal to potentially fall in your favor. You gotta give to get. We know, this is coming from a non-GM, but we’ve seen enough.

We just sat here and watched the Mets make a trade we’ve been proposing for months. Did we need to make that exact deal? No. But we need to do something. Standing around and watching during an opportunistic offseason when the Yankees have more questions than answers as it pertains to their World Series aspirations is only going to make the concerns and media grow louder.

We don’t want to blame Brian Cashman. And he has time to turn it around. But if the Yankees are going to view Luis Severino as an “acquisition” once he returns from Tommy John or think a one-year stopgap option at shortstop will be the answer in the event LeMahieu leaves, then we’re just not sure where else to point the finger.

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