• Loading stock data...
Wednesday, March 4, 2026

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

Tigers, Red Wings Get New TV Home With Detroit SportsNet Launch

The Detroit venture is the latest in a series of team-based moves.

Another Young Pirates Phenom, Another High-Stakes Decision

The Pittsburgh teenage phenom is turning heads despite his young age.
Sep 28, 2025; San Diego, California, USA; San Diego Padres third baseman Manny Machado (13), left, and Jackson Merrill (3) celebrate after scoring during the first inning against the Arizona Diamondbacks at Petco Park.

Drew Brees, Joe Lacob Among Interested Padres Suitors

A record-setting deal could be in place by Opening Day.
Sep 28, 2025; Cumberland, Georgia, USA; Atlanta Braves pitcher Charlie Morton (50) waves to fans while walking to the dugout after pitching against the Pittsburgh Pirates during the second inning at Truist Park.

Braves Post 11% Increase in Revenue in 2025 to $732 Million

The MLB club said the formation of BravesVision leans in to specific advantages.

Featured Today

Nicole Silveira

The Tattoo Marking Membership in the Most Exclusive Club in Sports

For athletes, the Olympic rings tattoo is “about everything it took.”
Dec 25, 2025; Denver, Colorado, USA; Denver Nuggets forward Spencer Jones (21) reacts against the Minnesota Timberwolves during the second half at Ball Arena.
March 1, 2026

Young Athletes Have Entered Their LinkedIn Era

Athletes can’t play forever. Some are laying the groundwork for Act 2.
[Subscription Customers Only] Jun 15, 2025; Seattle, Washington, USA; Botafogo owner John Textor inside the stadium before the match during a group stage match of the 2025 FIFA Club World Cup at Lumen Field.
February 27, 2026

The American Sports Owners Feuding Over a French Soccer Team

John Textor is at odds with Michele Kang and investment giant Ares.
[Subscription Customers Only] Jul 13, 2025; East Rutherford, New Jersey, USA; Chelsea FC midfielder Cole Palmer (10) celebrates winning the final of the 2025 FIFA Club World Cup at MetLife Stadium
February 21, 2026

Soccer’s ‘Crown Jewels’ Are Devouring Smaller Clubs

Mega conglomerates are feeding a big business machine. Fans are furious.

Hawks Stand By ‘Magic City Monday’ Promotion

Al Horford and Luke Kornet criticized the strip club-themed night.
Jan 28, 2026; Melbourne, Victoria, Australia; Jessica Pegula of United States celebrates her victory over Amanda Anisimova of United States in the quarterfinals of the women’s singles at the Australian Open at Rod Laver Arena in Melbourne Park.
February 25, 2026

Pegula, Keys Blame ‘Tough’ Tennis Schedule for Rash of Withdrawals

Pegula won in Dubai, then withdrew from a WTA 250 event.
Jeffrey Epstein and Ghislaine Maxwell
February 27, 2026

Jeffrey Epstein Was Funding Maryland Girls Club Soccer Powerhouse

The team website thanked Epstein and Ghislaine Maxwell for their mid-2000s donations.
Sponsored

From USWNT Star to NWSL Franchise Founder

Leslie Osborne, former USWNT midfielder, shares how athletes are moving from the pitch to the ownership table.
Jack Draper
February 25, 2026

Indian Wells Triples the Prize Money for Mixed Doubles

The “Fifth Slam” is leaning in to the mixed doubles trend.
February 23, 2026

Serena Williams Now Eligible to Play But ‘No Word’ on Indian Wells..

Her sister, Venus, will play at the BNP Paribas Open.
February 23, 2026

Mexican Soccer Postponed Amid Violence With World Cup Months Away

Tennis and UFC events will continue as planned.
Anthony Kim
February 20, 2026

Inside Anthony Kim’s Chaotic Path to Stunning Victory at LIV Golf

Anthony Kim joined the 4Aces after Patrick Reed abruptly left LIV.