How likely is Brian Cashman to extend Aaron Judge?

New York Yankees outfielder Aaron Judge turned some heads earlier in the week when he he said “a goal” of his is to be a a lifetime Yankee. Judge has made comments like this before, but coming before his last season prior to free agency, any extension talks are a bit more pressing. After another All-Star and Silver Slugger season, Judge will certainly command a lot of money, especially being the Yankees’ first home-grown offensive star in quite some time. However, history suggests that General Manager Brian Cashman may not get a deal done.

While the Yankees are, of course, willing to spend pretty pennies in free agency, contract extensions are less common for the team to do, especially for hitters and also a player of Judge’s caliber. Most recently, the team extended center fielder Aaron Hicks through 2025 for $64 million, and how that’s working out so far isn’t terribly inspiring with Hicks having missed virtually all of the 2021 season. Brett Gardner was also extended before 2014 with a year remaining until free agency for four years and $52 million. The only true long, “lifetime” extension Cashman has given out in recent years was CC Sabathia’s in 2011, which was negotiated to avoid him opting out of his preexisting deal.

Cashman appears to have no qualms about letting even his best stars reach free agency if the negotiations are not going to his liking. If he let Mariano Rivera and Derek Jeter reach free agent status, do you really think he’d lose any sleep about letting Judge do it too? For Rivera and Jeter, there was almost zero chance they’d sign with any other team. If Judge reaches free agency, there will doubtless be very many other teams legitimately bidding for his services.

One major sticking point on the years and total dollar amount Judge will receive is his age. Judge will turn 30 in April, which suggests his peak may already be over or will be soon. Judge, a former MVP runner-up (and should-be winner) is not going to settle for a short-term deal, though, suggesting his team and Cashman could very well be at an impasse all offseason.

His lengthy injury history doesn’t help dispel the notion that he won’t age well over the length of a long contract either. Hicks and Gardner were 29 and 31 years old, respectively, when they received their extensions, so it’s certainly been done by Cashman before, but both of their deals pale in comparison to what Judge will get, either through an extension or in free agency. And both have dealt with injuries and underperformance — neither are necessarily deals the Yankees would do again if they had the chance to change history.

For all the money that the Yankees have, Cashman has spent recent years preaching the importance of financial flexibility. While all of that flexibility has yet to win the Yankees a pennant in over a decade, this doesn’t appear to be changing as a practice any time soon. Regardless of how much you like Judge, it would probably be financially prudent to see if he can get through another largely healthy season before deciding how much money to commit to him. That, plus Brian Cashman’s history, means Judge and the fans will probably have to wait another year to find out if their star outfielder will really be a Yankee for life.