• Loading stock data...
Sunday, December 14, 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. 

YES ‘Satisfied’ Aaron Judge’s Historic HR Came During Its Telecast

Despite attempted horse-trading among national channels, Aaron Judge hit his historic 62nd…
October 5, 2022

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.

Linkedin
Whatsapp
Copy Link
Link Copied
Link Copied

What to Read

MLB Offseason Spending Heats Up With Trio of Big-Money Deals

A trio of deals this week is expected to loosen the market.
Visalia Rawhide played their home opener Tuesday, April 11, 2023 against the Rancho Cucamonga Quakes.

Marc Lasry’s PE Firm Steps Into Minor League Baseball

Avenue Sports Fund’s new entity, OnDeck, has acquired two MiLB teams.
Sep 20, 2025; Chicago, Illinois, USA; Chicago White Sox pitcher Yoendrys G—mez (94) delivers during the first inning against the San Diego Padres at Rate Field.

Winners and Losers in MLB Draft Lottery

The Southside Chicago club will get its first No. 1 pick since 1977.
Pete Alonso

David Rubenstein’s Orioles Finally Give Free Agent Huge Contract

Pete Alonso is leaving New York after seven seasons.

Featured Today

How Pickleball Became One Massive Private-Equity Rollup

Pickleball roads lead back to billionaire Tom Dundon.
Dec 9, 2025; Toronto, Ontario, CAN; New York Knicks guard Jalen Brunson (11) dribbles against Toronto Raptors guard Jamal Shead (23) during the first half at the 2025-26 NBA Emirates Cup at Scotiabank Arena
December 13, 2025

The Lucrative NBA Cup Is Here to Stay

The in-season tournament, launched in 2023, is turning into a staple.
The Los Angeles Chargers host executives from UCLA Health on Wednesday, August 7, 2024 at The Bolt in El Segundo, CA.
December 7, 2025

The Multibillion-Dollar Business of Pro Athlete Recovery

What started as ice baths has evolved into a multibillion-dollar industry.
Big League Wiffle Ball
November 29, 2025

Celebrity-Backed Wiffle Ball Has Big-League Aspirations

Big League Wiffle Ball team owners include Kevin Costner and David Adelman.

Caitlin Clark Says She’s ‘100%’ in Return to Court at USA Camp

Caitlin Clark returned to the court at full strength for USA Basketball.
Trinity Rodman
December 11, 2025

NWSL Will Vote on Seismic Rule Change to Keep Stars Like Rodman

The battle over Trinity Rodman’s future could reshape the NWSL.
Tennis
December 11, 2025

Tennis Pro Suspended 20 Years for Alleged Match-Fixing Syndicate

Quentin Folliot was also fined $70,000.
Sponsored

20 Years of Coastal Cool: How Johnnie-O Became a Force in Golf,..

A style movement powering one of the fastest-growing brands in sports and lifestyle.
Jan 18, 2024; Calgary, Alberta, CAN; Calgary Flames center Dillon Dube (29) against the Toronto Maple Leafs during the first period at Scotiabank Saddledome.
December 10, 2025

Third Hockey Canada Trial Defendant Signs U.S. Pro Deal

Dillon Dubé signed a professional tryout agreement with the Blues’ AHL affiliate.
Sabalenka
December 10, 2025

Sabalenka’s Battle of the Sexes Promo Turns Into Tennis Media Mess

An edited interview led to a mixup on Piers Morgan’s show Tuesday night.
Sponsored

20 Years of Coastal Cool: How Johnnie-O Became a Force in Golf,..

A style movement powering one of the fastest-growing brands in sports and lifestyle.
December 9, 2025

Colts Sign 44-Year-Old Philip Rivers to Practice Squad

Rivers last played for the Colts in 2020.