Will the Yankees keep Brian Cashman as general manager moving forward?

Alexander Wilson
New York Yankees, Brian Cashman
Dec 11, 2017; Orlando, FL, USA; New York Yankees general manager Brian Cashman reacts as outfielder Giancarlo Stanton (not pictured) is introduced at a press conference at Walt Disney World Swan and Dolphin Resort. Mandatory Credit: Kim Klement-USA TODAY Sports

The New York Yankees may have their sights set on extending Aaron Judge, but they also have to deal with the contract of general manager Brian Cashman. Cashman‘s current deal expires on December 31, so the Yankees still have him locked in for the next two months before the new year.

While some may argue that owner Hal Steinbrenner should move on from Cashman given the many blunders he’s made over the years, leading to premature playoff exits — being a perennial playoff team isn’t a bad thing at the end of the day.

Ultimately, the Yankees remain in contention every single season, thanks to a ton of financial commitments.

Nonetheless, the expectation is Cashman will be extended, given his long-standing relationship with the Steinbrenner’s and the connections he’s created in New York. He understands how to maneuver around this market and brush off the criticism, but that doesn’t avoid the fact that the Yankees haven’t been to the World Series in over a decade.

No word yet on a new contract, but one source said it’s “100 percent” Yankees general manager Brian Cashman will be back. Cashman’s deal expires Dec. 31.

Per Jon Heyman of the New York Post

The Yankees need better big-money decisions from Brian Cashman:

Oddly, Brian has struck gold on smaller players like Nestor Cortés, Jose Treviño, Clay Holmes, and Matt Carpenter this past season. However, his bigger signing seem to flop at an astronomical pace. Looking back at the contract he delivered Jacoby Ellsbury, Giancarlo Stanton‘s value up to this point, Aroldis Chapman struggling the past few seasons, and many more inefficient decisions.

Cashman now has to turn his attention to Aaron Judge, who he lowballed before the 2022 season began. A seven-year deal worth $31.5 million per season was never going to get it done, and Judge increased his price tag by millions, likely even surpassing 36 per year.

It will be interesting to see how much flexibility Cashman has in the financial department, but luckily, he has a few big-money players hitting the free agent market, notably Chapman and Zach Britton, who account for $30 million in savings.