Coming off arguably the greatest walk year ever, Aaron Judge can expect a monster payday this offseason. Judge will undoubtedly be the subject of a high-stakes bidding war between the Yankees (prohibitive favorites to retain the prolific slugger at -165 odds on DraftKings Sportsbook), Giants and Dodgers, with the Mets in play as a potential dark horse (despite assurances owner Steve Cohen won’t risk his relationship with Hal Steinbrenner) if all else fails.
As phenomenal as he was this past season, flirting with what would have been only the second Triple Crown in the past half-century, Judge still carries question marks about his age (he’ll be 31 next spring), durability and how he’ll adjust to his new surroundings if he leaves the decidedly-hitter-friendly dimensions of Yankee Stadium, particularly its laughable right-field porch (314 feet from home plate).

Judge’s decision to bet on himself was the right one, raising his value exponentially after declining a seven-year, $213.5-million extension that, in retrospect, seems almost insulting. Whether it comes from the Yankees, Giants (who are prepared to move heaven and earth to bring the prodigal son back to his rightful home in Northern California), the deep-pocketed Dodgers or a mystery team lying in wait, Judge has a pot of gold waiting for him at the end of his free-agent rainbow, a nine-figure sum Tim Britton of The Athletic predicts will make him the highest-paid position player in MLB history.
While the deal Judge signs this offseason is unlikely to rival the length of Bryce Harper’s mammoth, 13-year contract, Britton feels $320 million over eight years is a reasonable expectation, arguing the likely American League MVP has significantly outperformed Anthony Rendon and Francisco Lindor, both of whom are pocketing well north of $30 million annually.
“He’s closer, but maybe not all the way to, where Alex Rodriguez was when he signed his landmark 10-year deal with Texas. The difference with Judge is his age, obviously; he’ll be 31 next season, not 25 like Rodriguez. [Robinson] Cano got his 10-year deal entering his age-31 season nine winters ago, but since then, no one that age has signed an open-market deal for more than seven years,” writes Britton. “In recent years, we’ve seen some teams sign exceptionally long-term deals through age-38 or age-39 seasons with younger stars like Mike Trout, Bryce Harper and Mookie Betts. That would work as an eight or nine-year deal for Judge.”
The Yankees have until next Tuesday at 4 PM ET to extend the All-Star outfielder a one-year, $19.25-million qualifying offer, which he’ll presumably reject, assuring New York draft compensation in the event of Judge signing elsewhere. Other free agents of note this offseason include former NL batting champ Trea Turner, two-time Cy Young winner Jacob deGrom and Red Sox star Xander Bogaerts.
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