Will the Yankees extend their young stars?

Mea culpa: at this point, I hesitate to brand the Yankees as cheap, as I have implied in past articles. Instead, I will say the Yankees have been meticulous about how they spend their money. They have shown a reluctance to hand out lucrative long-term contracts to free agents, but they haven’t been shy about granting short-term contracts to “Tier two" free agents, even if it means going over the luxury tax. Judging from such behavior, the Yankees seem to be committed to securing long-term flexibility and avoiding dead money.

If this hypothesis is correct, what matters for the Yankees when they consider whether to sign a given free agent or not isn’t the money involved per se, but the length of the contract. The question then arises: will the Yankees apply this same guiding principle when it comes to extending their young stars in the not-too-distant future?

For example, consider Aaron Judge, who based on past performance is likely to receive the most handsome payday out of the so-called Baby Bombers. Judge will enter free agency in the 2022-2023 offseason, following his age-31 season. Judge’s relatively late debut (he was 25 in his first full year) and immediate impact in the bigs make for an interesting conundrum - do you extend him now at the risk for of paying for his decline into his late thirties, or do you let him walk at 31, when he will likely still be productive?

Judging from the Yankees’ apparent aversion to long-term commitments, I’d wager that the Yankees will either let Judge test the market, or maybe even flip him for prospects as he nears free agency. Judge is indeed a mega-star, but his age and size will make him a more under unpredictable investment than the likes of Bryce Harper and Manny Machado are now, and look where the Yankees stand evenon that front. I think the current front office is content to reap the benefits of Judge’s team control years when he is vastly underpaid, much like they did with Robinson Cano.

Of course, I’m not arguing that the Yankees will let everyone walk. If not Judge, I’m sure the Yankees will at least make an attempt to retain one of Luis Severino or Gary Sanchez, if only due to positional scarcity. But the Yankees’ recent modus operandi forces me to harbor doubts about the prospect of the current core being intact in five years’ time. It seems like they value having the necessary resources to address team needs at any given point, rather than tying current stars to the roster in an attempt to prevent talent from slipping away and making future roster construction more straightforward.

At this point I’m kind of tired of arguing the merits and demerits of the Yankees’ “flexibility over all” strategy. Yet I will say this: that strategy is based on two assumptions. One is that there will always be readily available talent on the market for the Yankees to supplement their core. Another is that the Yankees will be able to maintain a core of young, cost-controlled talent in the years to come even beyond the current crop of Judge, Sanchez, Severino and co., via the acquisition of blue-chip prospects or developing their own. I’m not so sure these are any more safer or riskier than biting the bullet on long-term investments.