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Thursday, September 18, 2025

Aaron Judge Could Command Record $500M In Free Agency

  • Leigh Steinberg thinks Yankees superstar could score $500 million, 10-year deal.
  • Judge is “an immediate box office draw,” Steinberg tells FOS.
Brad Penner-USA TODAY Sports

$500 million. 10 years. All guaranteed.

That’s the monster deal New York Yankees superstar Aaron Judge could land as he enters free agency, according to super-agent Leigh Steinberg.

That would be the richest player deal in Major League Baseball history. But if there’s anybody who could become baseball’s first $500 million player, its Judge, who set the new American League record with 62 home runs this season. 

“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,” Steinberg told Front Office Sports. “So he might be one of the few players who pays for part of his contract in ticket sales.”

Steinberg, the real-life inspiration for the movie “Jerry Maguire,” knows whereof he speaks. He negotiated the biggest contract in the NFL — Patrick Mahomes’ $450 million, 10-year deal. Over his 40-year career, Steinberg has secured $4 billion worth of contracts for over 300 athlete clients. 

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Judge turned down a seven-year, $213.5 million extension with the Yankees to test the potentially lucrative waters of unrestricted free agency. His bold decision is about to pay off.

A $50 million per-year contract would more than double his current $19 million a year salary. A 10-year pact would take the 30-year-old right fielder through his 40th birthday in 2032. 

Here’s how Judge’s potential deal would stack up against the highest-paid players in MLB via Spotrac:

  • Mike Trout, Los Angeles Angels: $426.5 million, 12 years.
  • Mookie Betts, Los Angeles Dodgers: $365 million, 12 years.
  • Francisco Lindor, New York Mets: $341 million, 10 years.

MLB teams are loath to guarantee contracts as players enter the twilight of their careers. But the 2017 Rookie of the Year might be one of the few who can pull it off, Steinberg said.

The towering 6’7” slugger is the best player on the most famous baseball team in the country’s largest TV market. The home-grown Yankee is coming off the best year of his career in which he nearly won the AL’s Triple Crown with 62 home runs, 131 RBI, and a .311 batting average.

If the Yankees don’t pay up, their cross-town rivals in Queens are waiting in the wings. 

With a net worth of $15 billion, Mets owner Steve Cohen is the richest majority owner in MLB. Cohen bought the Mets for $2.4 billion in 2020. He proved with his Lindor signing that he’s willing to pay big money to bring a winner to Citi Field.

Potential bidders such as the San Francisco Giants or other clubs would have to weigh whether they want to pay a luxury tax for their increased payrolls. The issue for Judge, said Steinberg, is how many guaranteed years he gets under his new contract.

“The question is: Are you paying a long-term contract for past performance? Or future projected performance? But if a franchise was going to make a bet on future productivity, he’s about the best candidate around,” said the chairman of Steinberg Sports & Entertainment.

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