The 2023 Offseason is Brian Cashman's Biggest Test Yet

  Now that the World Series is over five days from now the offseason begins. With that in mind, this is the biggest offseason that Brian Cashman will have in his 25-year tenure as Yankee General Manager. For the first time since 2016 the Bronx Bombers watched the postseason from their couches, and they earned that right.

Amazingly, this team finished over .500, although not that far above that mark. This iteration of the Bronx Bombers finish with the same record as that 2016 team—but the feeling with this squad feels different. Following the 2016 season, there was hope of the two power bats that would usher in the “Baby Bombers,” and in that offseason, the farm system was rated in the Top 10 in all of baseball. There was almost certainty that Brian Cashman would put a championship team around Aaron Judge, Gary Sanchez, Greg Bird, and Luis Severino that would be a title contender for years to come. There was hope. And that hope almost turned into reality. Almost.

But, that was then and this is now.

This time around the only hope coming from the Yankee fanbase is from the standpoint that Majority Owner Hal Steinbrenner will move on from Brian Cashman and Aaron Boone and from the blind obedience to analytical thinking. It is that thought and that thought alone that will reinvigorate this fanbase. Not some once in a lifetime signing. However, that hope will not become reality. At least not this season. All of that certainty in Brian Cashman and his front office has gone away. The Bronx hasn’t captured a title in 14 years. That means Cashman is starring the franchise's longest championship drought (18) right in the face with each passing day. The organization undoubtedly knows this and is dealing with the current situation of the ballclub and is stuck between a rock and a hard place. Either they can change the way they go about business, tell their fans they will do so while also trying to compete for a championship, or double down, and in turn spend more money to fix up the holes on the roster that have been issues because the organization has been following a failing process.

When it comes to the actual roster there is hope in two different avenues. There is a slim gleamingly of hope that the Yankees can somehow  move on from Giancarlo Stanton. That hope, at least this offseason, will not become reality due to his play on the field, his physical state, and the amount of money owed to him. Stanton has not delivered on his MVP talent outside of one postseason in 2020. He has for the large part been a failure because he hasn’t been on the field and even when he has, he has aged at an alarming rate. The second avenue is a Juan Soto trade. Right now, the 25-year-old Superstar left fielder doesn’t seem like he is Bronx bound even with all the preliminary reporting. It is still early, and the Bombers do have the capital to make a trade of that magnitude happen, but that would be a complete 180 from how Brian Cashman operated about 15 months ago.  

Further, at some point the elephant in the room needs to be addressed by the Yankees themselves. And that two-ton uncomfortable conversation comes in the form of an organizational audit.

The independent audit doesn’t seem like it is going to be/was (we still don’t know if the audit happened or if it will happen at all) what the Yankee fan base was sold when it was reported. Supposedly the company that came in at seasons’ end/or is still yet to come, would take a wholesale look at the way the Yankees operate. Hal Steinbrenner then has to do something he hasn’t truly done since taking over as the Principal Yankee Owner, operate like a shrewd businessman. AND, everyone else in the front office also needs to follow suit.

Cashman needs to address not only the organizational philosophy, the roster itself, but also why there is a revolving door going into the athletic trainer’s office. Figuring out the long-term health for the length of a full season is paramount. Changing the way the team plays on the field needs to change because it hasn’t resulted in a World Series or even a trip to the fall classic. After that, you can get to the needs of the squad on the field, and that starts with the bullpen.

If you look at team ERA, the Yankees are the best team in baseball. When you watch this bullpen daily, they look more like middle of the road. Part of this has to do with the injury issue because many arms have gone down over the course of the season because of numerous reasons, but even when healthy there is nobody in the bullpen that has a defined role. There is no closer. There is no reliable left specialist. There are no innings eaters. There is no Swiss army knife that every dominant bullpen has (just look at the past few champions they all have one). If the Yankees cannot build up the starting staff to go longer than five innings, yes, no matter what you do to the bullpen by July 1st it will burn out. But when there is no stability to go along with a lack of starter depth that is how you allow games that shouldn’t be losses become them.

When it comes to every day players; the Bombers don’t have an everyday left and center fielder at the current moment. There is a platoon at third base, an unknown at first, and a roadblock at catcher. Everson Pereira had a decent season, but he will continue to carry rookie status in 2024 and didn’t play well enough to hand over the keys of the left field job to him. There isn’t another player in the organization that will challenge Pereira in Spring Training. That means Brian Cashman either must make the Juan Soto trade or sign someone outside the organization. While in center field whoever the Yankees sign will be a cheap stopgap player as Jasson Dominguez recovers from Tommy John Surgery. The third base job between Oswald Peraza and DJ LeMahieu will play itself out over the course of Spring Training and the early part of the regular season. Peraza, when given his second chance in September, did make the most out of it looking like he could be a good player for a long time. LeMahieu, while struggling for the majority of the season, found something in the second half under interim hitting coach Sean Casey. At first the reason there is an unknown is because nobody knows how Anthony Rizzo will play after dealing with concussion symptoms for almost two months that ended his season. While with the catching position—there are just too many players for too few spots. Jose Trevino coming off wrist surgery will have to prove he is the same player he was prior to the surgery in the hopes he returns to All-Star form. The backup spot is where it gets messy. Either Austin Wells will have to start the season in the minors, or the Yankees will have to package Kyle Higashioka or Ben Rortvedt in a deal. Higashioka is the longest tenured Yankee and has shown real leadership within the Bomber clubhouse, so moving on from Higashioka would have to lead to a real upgrade elsewhere on the roster. Rortvedt has almost no value because he hasn’t played much in the two years he has been in the Bronx and hasn’t shown a clear quality that would be a key selling point when he is on the field. Unless the Yankees put a point of emphasis on playing Wells at first base some in Spring Training, it is highly unlikely that the Yanks break camp with three catchers on roster and something will happen.

The future and present for the Yankees seem to be in a holding pattern waiting for a picture-perfect situation to fall out of the sky. However, if you believe the bill of goods being sold to you out of the Bronx, then the Yankees will look themselves in the mirror this offseason. In order to get the Death Star and Evil Empire back to being fully operational they will need to act on the reflection they see staring back at them. Even if they disagree with what they are seeing…