Yankees: Why is Brian Cashman Still Here?

MLB: Washington Nationals at New York Yankees

The 2023 MLB season for the New York Yankees was an absolute disaster. The team failed to make the playoffs this season, though, they were lucky to have an above .500 record (82-80). Much of the blame for this season has been directed toward Yankees General Manager and Senior Vice President Brian Cashman.

He has made a ton of questionable moves in the past few years, but four truly stood out as they ended up hurting the Yankees last season, and one other move that was a disaster previously. This has prompted fans to ask the question, “Why is Brian Cashman still here?”

1. The most obvious failure this season was the whole Josh Donaldson Saga

Josh Donaldson was an absolute disaster for the Yankees last season. It seems the only reason why New York acquired Donaldson was because Cashman wanted to get rid of Gary Sanchez.

That turned out to be a Disaster with the amount of injuries that he has suffered and even when healthy, Donaldson just declined so much that his hitting power and technique were abysmal. The defense with Donaldson was not great either, which was another reason why Cashman wanted to do the deal as explained in the quote below.

The Donaldson saga worked so well for the Yankees that the team ended up just releasing him mid-season. It’s difficult to say which addition was worse during his tenure: Joey Gallo or Josh Donaldson.

The Gallo deal was probably worse as at least in the Donaldson deal the Yankees got a decent utility player in Isiah Kiner-Falefa. In the Gallo deal it hurts because one of the prospects in the deal was Ezequiel Duran who has done well with the Texas Rangers.

At least the Yankees managed to trade Gallo for something instead of straight-up releasing him as they did with Donaldson.

2. The Yankees’ Gamble of Frankie Montas has not paid off

Many criticize the Yankees for the Carlos Rodon signing, but at the time, it seemed like a reasonable contract. Unfortunately, it didn’t turn out well due to injuries. However, the real deal that was a lot worse was when Cashman acquired Frankie Montas from the Oakland Athletics.

In the transaction, the Yankees acquired both Frankie Montas and Lou Trivino in exchange for JP Sears, Ken Waldichuk, Luis Medina, and Cooper Bowman. Both Trivino and Montas missed most of the season due to injuries. As of now, Montas is a free agent, and Trivino might not be the same pitcher coming off Tommy John surgery.

The prospects that the Yankees gave up could have been more useful to the team compared to Montas and Trivino, both in the present and future. This move damaged the team’s present, and we will see how much damage it produces when the prospects fully develop. At least Cashman took the blame for making this deal.

3. The Terrible Overpay of Aaron Hicks

Aaron Hicks had shown flashes of potential but also inconsistency during his time with the Yankees. The extension seemed like a substantial commitment for a player who had only one standout season. The move was met with skepticism by many fans and analysts.

Hicks was eventually released as the team just lost faith in him. That release resulted in significant financial implications for the Yankees and left a void in the outfield. That void was intended to eventually be filled by top prospect Jasson Dominguez. Unfortunately, Dominguez’s injury added to the woes, and his availability in 2024 became uncertain with how he Tore his UCL last season.

In hindsight, this extension is considered a costly mistake for the Yankees, given its long-term effects and financial implications. It’s one of the moves that have generated criticism and frustration among the fan base.

4. Staying Mostly Quiet at the Trade Deadline

This was highly infuriating for Yankees fans because it was evident that the team needed to make changes with the clear struggles they were facing. Given the team’s World Series aspirations, immediate changes were necessary. So, what did the team do at the trade deadline? Well, next to nothing.

The only moves the Yankees made were minor, acquiring Kenyan Middleton and Spencer Howard, essentially serving as band-aids for a struggling pitching rotation that is likely going to be overhauled in the offseason. With high expectations and the need to either be buyers or sellers, the Yankees opted for a mostly neutral approach, making minor moves, and Brian Cashman failed to deliver.

Perhaps a couple of major moves could have pushed the Yankees into a wild-card playoff spot.

Dishonorable Mention – Remember the Whole Jacoby Ellsbury saga

The move to sign Jacoby Ellsbury did not directly affect the 2023 MLB season for the Yankees, but it is often regarded as one of the worst contracts in Yankees history, and Cashman had involvement in this deal, so it has to be mentioned.

Jacoby Ellsbury signed a seven-year, $153 million deal to join the New York Yankees after strong seasons with the Boston Red Sox. However, signing him turned out to be an absolute disaster. Ellsbury was a below-average hitter with the team and kept getting injured, which ultimately ended his career. The Yankees had to part ways with him as a result.

When the Yankees finally made the move to release Ellsbury, it got messy. The team owed Ellsbury around $26 million (2020 Salary and the buyout for the 2021 season). The Yankees did not want to pay it due to Ellsbury receiving unauthorized medical care, which did not sit well with the Players Association. Eventually, it got settled, but this happening under Cashman’s tenure did not paint him or the Yankees’ organization in a good light with how this dragged on and trying to throw Ellsbury under the bus.

A majority of the moves Cashman has made have heavily flopped and while many 100% blame Aaron Boone, it’s not his fault that the GM made too many changes to the team and brought in the wrong pieces.

It is stunning that the Yankees have not decided to part ways with Cashman, especially after missing the playoffs where the expectation was the World Series. Maybe it has something to do with the fact the Yankees gave Cashman a multi-year extension and they don’t want to buy him out of his contract, but things need to change for this team and now.

What happened last year should have been a wake-up call and it was a clear sign that Cashman had to go. Yet they kept him which has been a headscratcher and will continue to be for the time being.

Cashman needs the Yankees to make the playoffs next season. Especially with ownership facing pressure from fans after the disappointing season and a ton of people are questioning why Cashman is still here. It is playoffs or bust and if that does not happen, Cashman could be out of a job as Steinbrenner likely can’t take another disappointing season.

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