Yankees, Cashman Should Part Ways

Yankees Cashman

After another postseason exit at the hands of the Houston Astros, the New York Yankees find themselves at a crossroads. Longtime general manager Brian Cashman’s contract is up, and early indications suggest he will return. However, the team needs to look in the mirror and carefully consider whether Cashman should come back. The Yankees have failed to reach the World Series since their championship year of 2009. While they are a near-perennial playoff team, they lose for basically the same reason every year: their offense goes to bed in October. This suggests issues with roster construction, which should be blamed on the front office. Cashman is certainly capable of putting together a competitive roster, but it’s clear he’s not the person to get the Yankees over the hump. At this point, bringing on a fresh face as GM would set them up better for the future.


Early Success Shouldn’t Justify Cashman’s Return

A major reason Brian Cashman has lasted for so long is the Yankees’ championship legacy of years past. As soon as he took over the top front office job, the Yankees won three straight World Series from 1998 to 2000. However, most players on those teams were added under prior leadership. In particular, former GM Gene Michael drafted or signed a lot of the homegrown talent (i.e. Derek Jeter, Mariano Rivera, Andy Pettitte, Jorge Posada, etc.) forming the Yankee dynasty. That’s not to say Cashman deserves no credit for those titles. Certain offseason and midseason additions he made likely helped the Yankees over the finish line. But they had already laid a competitive foundation upon his ascension to the top job.

To Cashman’s credit, he successfully built a championship team in 2009. He made waves in the offseason by signing Mark Teixeira, CC Sabathia, A.J. Burnett, and Nick Swisher. Thanks largely to these signings, everything went right for the Yankees that year. They had a dominant regular season, and won every playoff series with relatively little sweat. Unfortunately, that core could not replicate their playoff success over the next few seasons, and the club entered a rebuilding phase in 2013.

In subsequent years, Cashman has shown an ability to build postseason teams. But they have not been good enough to get back to the World Series, losing in the ALCS five times since 2010, with three of those losses to Houston. Despite all of Cashman’s early success, it was so long ago now that it no longer makes sense to use it as a barometer of his performance. Failing to reach the World Series for over a decade with the resources at his disposal should be a bigger strike against Cashman than it currently seems to be.


A Missed Opportunity

Cashman has made a few questionable decisions in the last few years. These decisions now look particularly bad after how this postseason went. During the 2018-2019 offseason, both Bryce Harper and Manny Machado were available as free agents. It was a massive opportunity for the Yankees to sign a generational talent. At the time, Cashman made it clear up front that the team had no designs on Harper.



Among these six outfielders were Jacoby Ellsbury, who ended up being a disastrous signing, Jackson (then Clint) Frazier, who languished in the minors for an extended period before his brief Yankees tenure was limited by injuries, and Aaron Hicks, who was signed to a seven-year deal in 2019 that has looked increasingly bad since. Since signing with the Philadelphia Phillies that offseason, Harper has won an NL MVP, was largely responsible for the Phils’ magical run to this year’s World Series, and has continued his Hall of Fame trajectory.

The Yankees also passed on Machado, who ultimately signed with the San Diego Padres. He is a finalist for National League MVP this year and helped lead the Friars to their first NLCS appearance since 1998. Failing to sign either star, especially with how they looked in 2022, reflects badly on Cashman now. This is especially true in the case of Harper, who reportedly preferred the Yankees as a destination, and was willing to change positions to make it work. To not even reach out to him looks unforgivable in hindsight.


A Disastrous Trade

Another questionable decision by Cashman reared its’ ugly head in 2022, especially in the postseason. In March, he unloaded Gary Sanchez, who struggled with the Yankees the previous few seasons, and needed a change of scenery. He also gave up Gio Urshela, a very good two-way player who was a pleasant surprise during his Yankees tenure. In return for those two, the Minnesota Twins sent veteran third baseman Josh Donaldson, infielder Isiah Kiner-Falefa, and young catcher Ben Rortvedt. Throughout the season, Donaldson struggled at the plate despite being a plus defender. IKF possessed a roughly league-average bat in 2022, but was very subpar at shortstop, where the Yankees insisted on playing him despite his stronger defense at third base in prior years. Rortvedt saw no major-league action due to injury.

In the postseason, Donaldson was a major liability at the plate, striking out 16 times in 29 at-bats, and driving in no runs. Kiner-Falefa struggled in the field in October, with one error arguably costing them a game in the ALDS. He then tag-teamed a blunder with Gleyber Torres in Game Four against the Astros, botching a double play to help Houston complete their sweep. In recent days, Cashman praised Donaldson and expressed his intent to bring him back.



This seems puzzling at best to anyone who watched the Yankees regularly this season. Donaldson was a great player at one point, a former All-Star and MVP, but he’s past his prime. Cashman helped the Twins massively by taking on Donaldson’s nearly $22 million salary for 2022. This enabled Minnesota to sign Carlos Correa, a prized free-agent target the Yankees had eyes on initially. Donaldson and IKF were two major reasons the Yankees came up short this year. They are also two prime examples of the Yankees’ perennial problem, an offense that can’t get it done in the most important month.

Rather than cutting their losses, the front office is floating them both as viable options for next year. This approach seems to go against the team’s stated annual goal of winning a World Series. It shows their satisfaction with the status quo, even though this team, as presently constructed, clearly cannot beat the Astros. If the front office cannot spot obvious weaknesses on the team, major changes should be on the table.


Yankees Should Move On from Cashman

It’s clear that the Yankees’ winning ways early in Brian Cashman’s tenure have earned him extensive goodwill with ownership. But while the team remains a perennial playoff contender, they haven’t won a World Series in 13 years. They haven’t even appeared in the Fall Classic during that time. This is a team that states every year that they hope to, and are built to, win a World Series. That is obviously a lofty aim, and of course it won’t happen every single year. But for a team with the Yankees’ resources, the fact that it’s always “close but no cigar” is unacceptable.

The Yankees need a front office shakeup. A core good enough to compete year after year is in place. But they cannot continue to fall short in the same areas, and hope the same approach will eventually work. Brian Cashman has done a lot of good for the Yankees organization. They have won a lot during his tenure. They always put a winning team on the field. For too long, though, it has not been a World Series-level team. It is time for the Yankees and Cashman to part ways. A new approach just might get them over the finish line.

Main Photo:
Embed from Getty Images

Players Mentioned:

Derek Jeter, Mariano Rivera, Andy Pettitte, Jorge Posada, Mark Teixeira, CC Sabathia, A.J. Burnett, Nick Swisher, Bryce Harper, Manny Machado, Jacoby Ellsbury, Jackson Frazier, Aaron Hicks, Gary Sanchez, Gio UrshelaJosh Donaldson, Isiah Kiner-Falefa, Ben Rortvedt, Gleyber Torres, Carlos Correa