Throughout history, the New York Yankees have had nothing but the greatest talents in baseball. Backed by their never-ending pool of financial resources, the Evil Empire became MLB's biggest juggernaut.

But the Brian Cashman - Hal Steinbrenner era hasn't been anything close to that. If anything, they've missed the chance to sign or trade for multiple stars, just to end up trading for bad contracts or overpaying for players just to keep them there.

That's why there's some legit concern about them messing up again and losing Aaron Judge in free agency. However, Cashman seems pretty confident in the team's ability to retain the reigning AL MVP.

MLB News: Brian Cashman Says Yankees Are Being Very Aggressive In Pursuit Of Aaron Judge

“It’s his dance card,” Cashman said, per MLB.com. “He’s a free agent. He has a chance to make decisions for him and his family. I can tell you that we are negotiating hard. [Yankees managing general partner] Hal Steinbrenner has been very public. I can tell you Hal is putting his money where his mouth is, where he told his fan base he was going to make every effort to sign this player.”

“We’d love to have our player back,” Cashman added. “We’d love to be able to continue to call him our player every step of the way as he follows what looks like -- as long as nothing happens -- a career path right to Cooperstown. We’d love it to be in pinstripes every step of the way. At the same time, there’s competition. Who they are or how many, I couldn’t tell you. I just know we’re putting our best foot forward and feel we have a lot to offer.”

According to the latest reports, the Yankees have already reached out with an eight-year deal that would exceed the $300 million plateau. However, the San Francisco Giants, Los Angeles Dodgers and several other suitors could reportedly even top that figure.

All things considered, the Yankees cannot afford to lose a generational player like Judge, especially after failing to go the distance and win the World Series since 2009. Should that be the case, then there wouldn't be a single valid reason why Brian Cashman should keep his job.