3 tough offseason decisions Yankees need to make, but won't

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Aaron Judge said it. These New York Yankees need many a change to fix whatever's broken. The injuries. The lack of depth. The prospects that flame out once they reach MLB. The complacency. The will to win. Making contact! It all seems so simple, but the Bombers have made it look incredilbly difficult for four years now.

This offseason, there's no doubt the front office (and Hal Steinbrenner) will be working tirelessly to alter the perception that's now dominated the baseball sphere: the Yankees are weak, underwhelming, and far behind the curve.

That means drastic decision making needs to be on the horizon -- something the Yankees are usually hesitant to orchestrate, unless it's something beyond unexpected and detrimental to team chemistry (see: every trade deadline deal since 2021).

Heading into 2024, the Yankees are in grave danger of wasting another year of Aaron Judge's and Gerrit Cole's primes. The 2021 and 2023 seasons have already done enough damage.

But does the organization have the guts to make ruthless moves in order to improve the bigger picture? Probably not, but here's what needs to be done.

3 tough offseason decisions Yankees need to make, but won't

Sell high on someone: Gleyber Torres? Clarke Schmidt? Top pitching prospects?

This is the move they're most likely to make because Brian Cashman loves disrupting the balance of the roster. But in our eyes, it's still unlikely. He's probably not going to get the value he seeks in any trade, which usually halts negotiations rather swiftly for the Yanks.

Torres is the obvious one, solely because he's been in rumors for the better part of a year and probably won't be on the team beyond 2024. Is it the best decision for the Yankees to trade their second-best hitter? Not exactly, but if they can address multiple needs by moving him, then they should. After all, Torres shouldn't be your second-best hitter -- that's how deep the Yankees' problems run.

Clarke Schmidt is another option, but he didn't end the year on a high note and represents an asset the Yankees probably shouldn't part with. A controllable starter through 2027? Teams kill for that. And the Yankees need starting pitching. But again, if the price is right, this deal has to happen.

Same goes for Austin Wells + the Yankees' glut of highly-rated top prospects. Wells, in theory, shouldn't get in the way of a Juan Soto trade. Nor should any of the team's top prospects outside of Jasson Dominguez. The Yankees need to be aggressive in the right ways this time around. They won't be, though. We can assure you of that.

Trade Giancarlo Stanton and/or DJ LeMahieu at any cost

With that aggression, costs be damned! Again, that's no longer part of the Yankee way. Every investment is calculated down to the penny and every risk factor is considered before Cashman dips his quill in ink and signs off on it. It's exhausting and rarely produces results.

But the reality is there needs to be some level of carelessness on the financial front. They gave $360 million to Judge and $162 million to Carlos Rodón, which was a start, but now it's time to cut bait with more distressed assets and pay for them to leave.

Aaron Hicks was the start of that, but he wasn't necessarily the entire problem. The Yankees played a very big role in his struggles. But that $30 million sacrifice was clearly tough for Steinbrenner and Co. to swallow.

So they might be dry heaving over the toilet thinking about Giancarlo Stanton's remaining $88 million and DJ LeMahieu's remaining $45 million. But one of them needs to go (Stanton, definitely) if this team wants to improve its flexibility and athleticism. Stanton can't hit. He can't run. He can't play defense.

But if that's too much for the Yankees to handle, trading LeMahieu and eating around ~$20 million of his remaining $45 should be on the table. LeMahieu's defensive versatility is an advantage, but his inconsistent offense, loss of power and nonexistent speed play roles in hampering the Yankees' offense. Though giving some underwhelming younger options a chance over DJLM isn't exactly enticing, it at least improves the team's athleticism and helps them project their future.

Stanton and LeMahieu have held the Yankees back in some capacity for some time now (Stanton on and off since 2019 and LeMahieu since 2021). Time to move on and find any marginal upgrade.

Give Brian Cashman a cushy front office job that doesn't matter and bring in a new baseball operations person

And finally, give the people what they want! Cashman is no longer suited to call the shots for the Yankees. He cannot be the one signing off on decisions that shape the future or even improve the immediate outlook. How much longer can the Yankees stomach his moves setting the organization back?

When you think about it, the Yankees' lone World Series victory since 2001 came in 2009 when Cashman was given the green light to spend $500 million as George Steinbrenner was knocking on heaven's door. Since then? It's been the most disappointing era of Yankees baseball since the pre-dynasty days. And the mishaps have all been self-inflicted.

Hal Steinbrenner was instrumental in cutting spending after the 2017 and 2018 seasons and left the duties to Cashman to make cost-effective moves to improve the roster. The 2018 roster flamed out hard in the playoffs. The 2019 roster endured an historic amount of injuries, chugged along nicely, but succumbed to the Astros in the ALCS. Then, from 2020 on, outside of the addition of Cole and re-signing Judge, very few Cashman moves have paid dividends (Clay Holmes, Jose Trevino, Wandy Peralta?). In fact, many have been disastrous (Joey Gallo, Josh Donaldson, Isiah Kiner-Falefa, Anthony Rizzo, Luis Severino, Aaron Hicks, Andrew Benintendi, Rougned Odor, Jay Bruce ... do we need to keep going?).

On top of that, the player development and drafting has been terrible The Yankees' homegrown, drafted WAR leaders since Cashman took over in 1998 are Brett Gardner, Aaron Judge and ... Anthony Volpe. It's actually insane.

The Yankees need a new direction. They don't want to fire Cashman? Fine. Elevate him to a position that doesn't matter -- one that makes it seem like he's the head honcho, but really just keeps him in a cushy role as legacy member of the front office. Bring in a forward-thinking GM and allow him/her to create their own front office and let Cashman be the guy the GM forces to sign off on whatever moves are being made.

The Most Special Assistant to Hal Steinbrenner? Yeah, we like that one. It makes the most sense, too.

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