The New York Yankees gave general manager Brian Cashman a new contract as their first order of business during the MLB Winter Meetings. However, his comments after signing the extension didn't exactly inspire confidence.

Cashman spoke to the media in San Diego on Monday. One of the topics brought up was current free agent superstar Aaron Judge. The Yankees GM said his team was in active negotiations with their potentially-former outfielder.

Despite this, Cashman revealed they were not aware Judge planned to be in person at the MLB Winter Meetings. Furthermore, they had no current plans to meet with the reigning AL MVP face-to-face.

Judge will reportedly be in San Diego on Tuesday, likely to meet face-to-face with interested teams. The superstar outfielder has not given assurances to New York that they can top another team's final offer.

“The way this winter is going to play out, it could take us down a lot of different roads we didn’t expect,” Cashman said Monday.

Besides the Yankees, the most interested team is the San Francisco Giants. He is currently expected to receive a nine-year contract with any team he signs with. And the Giants reportedly aren't interested in being outbid for the California native.

If Judge signs elsewhere, the Yankees must shift gears quickly. Unfortunately, replacing a player of Judge's caliber isn't easy. And there likely isn't a quick-fix free agent they can bring in to replace what they lost.

New York isn't out of the running until Judge signs on the dotted line elsewhere. However, Cashman's comments don't paint the brightest picture if you are a Yankees fan.