SAN DIEGO — The baseball players in the $300 million contract club have one obvious thing in common, but prior to this week’s MLB Winter Meetings, they shared something else, too: They all put pen to paper in their 20s.

All 10 of MLB's $300 million hitters played at least two seasons of those deals in their 20s. But Aaron Judge, who reportedly has a nine-year, $360 million agreement in place with the New York Yankees, is about to Kool-Aid Man his way right through that perceived barrier.

Unsurprisingly, all of the $300 million deals in baseball history are recent and ongoing, the earliest being Giancarlo Stanton’s extension signed in November 2014. Among them, you get a snapshot of what recent MLB front offices have viewed as super-elite players. And the overwhelming takeaway is that these sorts of contracts, nowadays, go to stars who are both great and young.

Fairly or unfairly, major deals for superstars in their fourth decade of life — Miguel Cabrera, Albert Pujols, Robinson Cano and (for somewhat different reasons) Alex Rodriguez — have been maligned as cautionary tales, identified as a metaphorical, dread-inducing species of contract called an “albatross.” No hitter over 30 had bested Cabrera’s eight-year, $248 million extension with the Detroit Tigers until Judge’s reported pact with the Yankees on Wednesday. Anthony Rendon, who turned 30 in June of the first season of his $245 million deal with the Los Angeles Angels, is perhaps the closest thing to a spiritual successor.

What the intervening years have seen instead is a rush to identify and sign superstars at earlier and earlier ages, preferably (for teams) before they ever reach an open market where a bidding war might ensue. Since Cabrera’s deal, MLB teams have combined a ruthless pursuit of efficiency with just enough life-changing money for the top talents, and extensions have become the norm for elite players. Mike Trout, Mookie Betts, Jose Ramirez, Francisco Lindor, Nolan Arenado, Jose Altuve: Those are the top six position players, by FanGraphs WAR, since Cabrera’s contract began in 2016, and not one of them has ever been a free agent.

Seventh, though, is Judge. And by rejecting the Yankees’ overture — a seven-year, $213.5 million extension — prior to 2022, he pressed baseball to grapple once again with the matter of an elite talent at a suboptimal age.

Younger, better, faster, stronger

MLB’s labor structure, which keeps players under team control for their first six seasons of major-league service, has long led to situations in which stars are vastly underpaid in their 20s, then finally rewarded for past performance as their skills wane.

In most cases, the disappointment of highly paid stars underperforming overshadows any consideration for the unfair financial purgatory the system already subjected them to. Fans boo. Players feel the double-whammy of declining ability and mounting antipathy. Team owners browbeat and dismiss the general managers who negotiated the deals. Most everyone winds up unhappy.

So before we rocket ahead and begin conceiving of this deal in hindsight, remember that this bitter reality is brewed by the system, not the players caught up in it. None of them has a responsibility to sacrifice money to make everyone else feel better. Judge believed he was worth more than the $213.5 million the Yankees offered in spring 2022. Then he swung it into existence by belting 62 homers and letting the open market have the final say.

Unfortunately, though, there’s one big, honking reason the Yankees of December 2022 committed $360 million to a soon-to-be-31-year-old: Because they didn’t have a 25-year-old to give it to instead.

It’s not difficult to process why teams have recently been working to sign elite stars to deals that cover, say, ages 25 to 35 instead of 30 to 40. Pre-free-agency deals for Betts, Lindor and others come with a lot of benefits even at huge total values. Namely, the structure can be more fitted to the team’s liking when there’s no bidding war involved, and there’s a wider realistic window to achieve a justifying payoff — in the form of a World Series, a record chase, an MVP, whatever.

The early-career deals for Wander Franco, Julio Rodriguez and even Fernando Tatis Jr. show that thesis at its most extreme. You can call the Tatis deal a disaster for the Padres over his injuries and (repeated instances of poor judgment) if you want, but are you really certain you won’t be proven dramatically wrong at any point before 2034?

The Yankees’ real albatross

Judge’s deal anticipates, at a fundamental level, a player worth about 5 Wins Above Replacement per season ($8 million per 1 WAR is a common shortcut for assessing value on the open market, though it often varies). Yet everyone knows it doesn’t work quite that cleanly. He’s capable of the extraordinary — his 2022 was worth 11.4 WAR per FanGraphs, his 2017 worth 8.7 WAR — but more often, he checks in right around that 5-WAR threshold.

Or, to be more precise, he has checked in around that threshold — past tense. But the aging curve for hitters is cruel, sapping peripheral skills such as baserunning and defense, which adds up and puts pressure on the bat to be even better … right as those hitting abilities start to dwindle as well.

It’s difficult to envision Judge as anything but a homer-bashing titan after the previous year, but history says his days of world domination are indeed numbered. Since integration in 1947, 35 hitters have recorded three or more seasons of 5-plus WAR in their age-31 seasons and beyond, according to Baseball-Reference. But since Barry Bonds’ last peak year in 2004, only three players have managed that feat: Adrian Beltre, Ichiro Suzuki and Ian Kinsler.

If you narrow the scope to hitters 6-foot-5 or taller, it’s even bleaker: Since 1947, Dave Winfield and John Olerud put up two 5-WAR seasons apiece, Mark McGwire did it five times (potentially, of course, with the assistance of performance-enhancing drugs), and no one else has done it more than once.

There’s no lesson there, just pure scarcity. The road ahead of Judge is depressingly difficult.

I’d bet Yankees GM Brian Cashman isn’t expecting 39-year-old Judge — or even 36-year-old Judge — to be a 5-WAR player. He and the Yankees’ front office probably aren’t even anticipating much more from Judge’s 2023 to 2031 seasons than they were this spring — before the Bonds impersonation and the 62 homers and the whole "carrying them through the summer while the rest of the lineup took a nap" thing.

The Yankees are looking at 2023, and perhaps 2024, and acknowledging that the best, most direct way to keep their competitive window wide open — an annual imperative in the Bronx — involves asking Judge to hold it there as they attempt to incorporate younger prospects, such as shortstop Anthony Volpe, while maximizing the tenures of other expensive stars, such as ace Gerrit Cole and outfielder Giancarlo Stanton.

In terms of the Yankees’ finances, Judge’s astoundingly great 2022 — and the resulting leap from $213.5 million to $360 million — was a black swan event, an entirely unforeseeable campaign that might stick around as a different large, metaphorical bird, if you’re into the shorthand for contracts that age poorly: an albatross.

The Yankees know how this works, though. Being the Yankees means they have to pony up in this moment — and that they have the money to do so. A little unpleasantness is the price of chasing a ringing achievement.

And Aaron Judge just showed how lucrative that can be.