Thursday, October 8, 2026
  • -
    days
  • -
    hours
  • -
    minutes
  • -
    seconds

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

Want more from Front Office Sports
in your search results?

Add Front Office Sports on Google

$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.

Download the FOS App

The business of sports, in your pocket.

QR code to download the app

Scan the QR code to get the app now.

Linkedin
Whatsapp
Copy Link
Link Copied
Link Copied

What to Read

Kenny Albert Fox Sports
First at FOS

Kenny Albert’s Last-Minute NLDS Fill-In Came Mid-Colonoscopy Prep

Albert filled in for Joe Davis, who had lost his voice.
Oct 4, 2026; Los Angeles, California, USA; Atlanta Braves pitcher Didier Fuentes (72) throws during the sixth inning against the Los Angeles Dodgers in game two of the NLDS for the 2026 MLB Playoffs at Uniqlo Field at Dodger Stadium.

MLB Division Series Extends Postseason Ratings Streak

Fox Sports and TNT Sports saw initial viewership lifts in the Division Series.

Jimmy Rollins: MLB Analytics Gurus Undervalue Team Chemistry

“I went to the college of MLB. Where’d you go?”
First at FOS

Yankee Stadium Quietly Suffered a Summer Peanut Shortage

The Yankees mysteriously ran out of peanuts this summer.
podcast thumbnail mobile
Front Office Sports Today

10/7/26 – EuroLeague Rejects NBA, LeBron’s Helicopter Sparks Backlash, $12M Super Bowl Ads

0:00

Featured Today

Oct 3, 2026; Starkville, Mississippi, USA; Alabama Crimson Tide head coach Kalen DeBoer waits to run onto the field prior to the game against the Mississippi State Bulldogs at Davis Wade Stadium at Scott Field. Mandatory Credit: Petre Thomas-Imagn Images

Who Is Alabama Football in Year 3 Under Kalen DeBoer?

The No. 6 Crimson Tide host No. 2 Georgia on Saturday.
Cubs behind the scenes
October 6, 2026

Hollywood and TikTok: Sports Media’s New ‘Blueprint’

Teams and leagues are pouring money into the quest for fans.
October 2, 2026

How the Baseball Cap Became a ‘Behemoth’

The hat has become essential for athletes, fans, and the sports-agnostic.
Morishita-Sato-homerun-celebration-at-Meiji-Jingu-Baseball-Staidum-2025
September 28, 2026

Japanese Baseball Is Fighting Back Against MLB Talent Drain

Nippon Professional Baseball is reimagining how to be a global juggernaut.
Aug 9, 2026; Bedminster, New Jersey, USA; President Donald Trump walks out of the clubhouse during the final round of the LIV Golf New York tournament at Trump National Bedminster.
September 25, 2026

Trump’s Year of Sports Gets Busier With CFB, Presidents Cup

The impact of Trump’s attendance varies across each sporting event.
Aug 23, 2026; Westfield, Indiana, USA; Jon Rahm tees off on hole 18 during the final round of the LIV Golf Indianapolis golf tournament at The Club at Chatham Hills.

Jon Rahm Will Not Participate in LIV 2.0

Rahm was LIV’s biggest star besides Bryson DeChambeau.
Jun 9, 2025; Phoenix, Arizona, USA; Arizona Diamondbacks pitcher Justin Martinez (63) throws against the Seattle Mariners in the ninth inning at Chase Field.
October 7, 2026

Another Startup Is Trying to Sell Shares in Athletes’ Future Earnings

“We are basically building a mini Robinhood,” Agentiq’s cofounder tells FOS.
October 7, 2026

Coco Gauff Says Racist Abuse Has Been ‘Draining’ at China Open

Gauff pulled out of the Wuhan Open after the match.
Sponsored

Beyond the Scorecard: How Dow Is Putting Purpose at the Center of Women’s Golf

Discover how Dow and the LPGA are building a partnership with lasting impact.
October 5, 2026

LeBron’s Fanatics Deal Includes Helicopter Use

The helicopter has repeatedly gone between NYC and Philly.
October 5, 2026

Alex Ovechkin Announces Retirement After 22 Seasons

The Capitals superstar said this season will be his last.
Tom Brady Raiders
September 30, 2026

Tom Brady Biographer Still Not Ruling Out NFL Comeback

Brady’s last NFL season was in 2022.
Sponsored

Beyond the Scorecard: How Dow Is Putting Purpose at the Center of Women’s Golf

Discover how Dow and the LPGA are building a partnership with lasting impact.