Aaron Judge free agency
Kirby Lee-USA TODAY Sports

The Yankees’ bid for a 28th World Series title just ended, but that means the Aaron Judge free agency train is now kicking into high gear.

Just how much will the slugger sign for this winter? We know he’s outperformed the $213.5 million extension New York offered him in March. The new AL single-season home run record holder outperformed it so much that his next contract will likely start with a “3” at the beginning.

Could he challenge Mike Trout for the richest contract in baseball history, though? Judge will be entering his age-31 season in 2023, and Trout’s $426.5 million deal seems out of reach…or is it? Agent Leigh Steinberg thinks the slugging outfielder will blow past that number.

Steinberg, who was the inspiration behind the movie, Jerry Maguire, discussed his reasoning for why Judge could command a half-billion dollars over a 10-year term with Front Office Sports:

He immediately and dramatically enhances a team’s offensive output. He’s a good team player. And for any team that’s not sold out, he’s an immediate box office draw. So he might be one of the few players who pays for part of his contract in ticket sales.

That reasoning is decent. It’s not like Steinberg (who doesn’t represent Judge) hasn’t been involved in these kinds of negotiations. He represents Kansas City Chiefs quarterback Pat Mahomes, who signed a 10-year, $450 million deal.

We didn’t get any details on how Steinberg would structure this deal outside of Judge earning $50 million per year. Many of MLB’s big-market teams will be interested in acquiring the outfielder. The crosstown Mets and baseball’s richest owner in Steve Cohen will at least do their due diligence.

Judge, a California native, will likely be courted by the San Francisco Giants and Los Angeles Dodgers, too. From recent reports, both teams are willing to do drastic things to sign the slugger. Los Angeles is reportedly thinking about moving Mookie Betts, a five-time Gold Glove right fielder, to second base. Meanwhile, the Giants are determined to land Judge and “won’t be underbid” in any negotiations.

This will be a fascinating series of events to watch unfold in the coming weeks. It’s clear that Judge will at least sign a contract between $300 and $400 million. But would a team actually go up to $500 million to give him no choice but to sign with them? Especially after we’ve seen how similar contracts have worked for other over 30 MLB stars (see Pujols, Albert and Cabrera, Miguel)?

I don’t know, folks. That seems doubtful to me, but who knows what’ll happen once the bidding officially starts? This seems like an unrealistic number, but the Aaron Judge free agency situation is one we’ve never experienced before.

Matt Musico can be reached at matt.musico@xlmedia.com and you can follow him on Twitter: @mmusico8.

Matt Musico is an editor for ESNY. He’s been writing about baseball and the Mets for the past decade. His work has been featured on numberFire, MetsMerized Online, Bleacher Report, and Yahoo! Sports.