• Loading stock data...
Thursday, December 25, 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

Sep 21, 2025; Kansas City, Missouri, USA; Kansas City Royals catcher Carter Jensen (22) hits a two run single against the Toronto Blue Jays during the fourth inning at Kauffman Stadium.

Chiefs’ New Stadium Site Is Set. Now It’s Royals’ Turn

The MLB club is also looking on both sides of the Missouri-Kansas border.
Rob Manfred
exclusive

MLB Teams Fear League Will Pick Winners and Losers in Tech

One company under consideration was founded by a top MLB exec’s uncle.
Sep 27, 2025; Philadelphia, Pennsylvania, USA; Minnesota Twins pitcher Kody Funderburk (55) and catch

Twins’ New Investments Value Club at $1.75 Billion

The Twins have also announced a succession plan.

Featured Today

Heated Rivalry (L to R) - Connor Storrie as Ilya Rozanov and Hudson Williams as Shane Hollander in Episode 104 of Heated Rivalry. Cr. Sabrina Lantos © 2025

Hockey Needed Some Virality. Then Came ‘Heated Rivalry’

No one was prepared for the Canadian show’s smash success.
December 23, 2025

What It Takes to Pull Off Florida’s First Outdoor NHL Game

The Rangers will face the Panthers in Miami’s first NHL Winter Classic.
December 14, 2025

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.
Sep 7, 2025; Flushing, NY, USA; Carlos Alcaraz (ESP) and Jannik Sinner (ITA) poses for a photo after the final of mens singles at Billie Jean King National Tennis Center

The Year of Carlos Alcaraz and Jannik Sinner

Novak Djokovic acknowledged that the duo are above the rest.
Dec 21, 2025; Detroit, Michigan, USA; Detroit Lions cornerback Rock Ya-Sin (23) tackles Pittsburgh Steelers wide receiver DK Metcalf (4) during the fourth quarter at Ford Field.
December 24, 2025

DK Metcalf Will Lose More Than $45M After NFL Upholds Suspension

The suspension voids $45 million in guaranteed money.
Sep 27, 2025; San Jose, California, USA; Bay FC forward Racheal Kundananji (9) takes a shot on goal against the Utah Royals in the second half at PayPal Park.
December 24, 2025

Some Women’s Soccer Stars Wouldn’t Qualify Under NWSL’s New ‘Rodman Rule’

Players oppose the policy and the union is planning to take action.
Sponsored

The Hidden Tech Behind Every Touchdown

Nearly two-thirds of NFL stadiums already rely on Cisco networks, and the Super Bowl will showcase the full scale of the partnership.
December 24, 2025

NBA Players Taking More Control Over Where Fine Money Goes

The NBPA matched $1.6 million in donations in the 2025 offseason.
Aug 22, 2025; Detroit, Michigan, USA; Brooks Koepka of Smash GC address the media after the quarterfinals of the LIV Golf Michigan Team Championship at The Cardinal at Saint John's Resort.
December 23, 2025

Brooks Koepka Leaving LIV Golf After Four Years

The golfer’s future on the PGA Tour or elsewhere is unclear.
December 23, 2025

NWSL Moves Forward With Star Rule After Players Rejected Plan

Players wanted to raise the salary cap instead.
December 22, 2025

DK Metcalf Suspended Two Games For Swinging at Fan

Metcalf plans to appeal.