The albatross lives: Aaron Jud...

SAN DIEGO (AP) — The baseball players in the $300 million deal club had one apparent thing in common, but they also shared something else before to this week's MLB Winter Meetings: they all signed contracts in their twenties.

All ten of MLB's $300 million batters spent at least two seasons of their contracts in their twenties. However, Aaron Judge, who has allegedly signed to a nine-year, $360 million contract with the New York Yankees, is going to Kool-Aid Man his way right through that supposed barrier.

Unsurprisingly, all of the $300 million contracts in baseball history are recent and continuing, with Giancarlo Stanton's extension inked in November 2014 being the most recent.

Instead, in the ensuing years, there has been a rush to find and sign superstars at younger and younger ages, preferably (for teams) before they reach an open market where a bidding war would begin. Since Cabrera's contract, MLB organizations have paired a merciless pursuit of efficiency with just enough life-changing money for the best talents, and exceptional player extensions have become the standard. Mike Trout, Mookie Betts, Jose Ramirez, Francisco Lindor, Nolan Arenado, and Jose Altuve are the best six position players according to FanGraphs WAR since Cabrera's deal began in 2016, yet none of them have ever been free agents.

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.

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.