• Loading stock data...
Wednesday, January 14, 2026

Aaron Judge’s Career Season Is Perfectly Timed

  • The four-time All-Star’s refusal is arguably one of the bolder business moves by a player in free agency.
  • The decision should pay off — maybe by an extra $100 million.
Brad Penner-USA TODAY Sports

New York Yankees slugger Aaron Judge spent this weekend chasing Roger Maris’ American League record of 61 homers, but so far has just fallen short. Whether he ties the record or not, however, he’s still sitting on a massive payday.

This offseason, the Yankees offered Judge a seven-year, $213.5 million extension, which would have been among the 20 most lucrative contracts in MLB.

The four-time All-Star’s refusal is one of the bolder business moves by a player in free agency. The decision should pay off — maybe by an extra $100 million — after one of the single greatest contract years since free agency’s inception in 1976.

  • Curt Flood’s refusal to be traded in 1969 ultimately paved the way for modern free agency itself — but torpedoed his own successful career.
  • In May, ESPN insider Jeff Passan estimated Judge could command at least $300 million, making him one of the 10 highest-paid players in MLB.
  • That estimation didn’t factor in the 30-year-old breaking a home run record and making runs for the Triple Crown and AL MVP.

All Rise (Especially Contract Leverage)

Yankees GM Brian Cashman will want to keep Judge in pinstripes, but other teams are chomping at the bit. Judge himself has hinted at being open to leaving the Bronx (he has jokingly spoken about his affection for Red Sox fans).

The fan who caught his 60th blast on Tuesday said he only hoped Judge would remain a Yankee next year.

Linkedin
Whatsapp
Copy Link
Link Copied
Link Copied

What to Read

May 30, 2024; Atlanta, Georgia, USA; A detailed view of a Washington Nationals hat and glove on the bench against the Atlanta Braves in the ninth inning at Truist Park.

Nats Are Latest Team to Join MLB Media Umbrella

The MLB club is departing the Orioles-controlled MASN after 21 years.

Fanatics Is Already in Apparel, Collectibles, Betting—Now It’s a Content Studio

The merchandising giant is pushing into a new business vertical again.
Sep 24, 2025; Toronto, Ontario, CAN; Boston Red Sox third baseman Alex Bregman (2) hits a single against the Toronto Blue Jays in the first inning at Rogers Centre.

Cubs Land Bregman Prize While Red Sox Questions Mount

The veteran third baseman leaves Boston after just one season.
Black Rabbit

The Netflix Star Who Makes Sure NBA Players Have Clean Towels

How a Nets staffer landed a breakout role on “Black Rabbit.”

Featured Today

NHL Ditched Its Dress Code. Hockey’s Fashion Era Arrived Quickly

With no dress code, impeccably dressed players are seeing big-money deals.
January 6, 2026

Hockey in Florida Was Once a Risk. Now It’s Thriving

The state of Florida has become a traditional—and highly lucrative—market.
Dec 30, 2025; Los Angeles, California, USA; Los Angeles Lakers guard Luka Doncic (77) reacts after scoring a basket against the Detroit Pistons during the second half at Crypto.com Arena
January 4, 2026

Why Pro Sports Team Valuations Will Keep Climbing in 2026

Asset scarcity and increasing media-rights deals underpin soaring valuations.
Imagn Images/Front Office Sports
January 2, 2026

FOS Crystal Ball: Predictions for the Business of Sports in 2026

Here’s what FOS journalists think could be on the horizon.
Bryson DeChambeau

Bryson DeChambeau: Doing Only Majors and YouTube ‘Incredibly Viable’

DeChambeau says choosing YouTube over LIV or PGA Tour is “incredibly viable.”
Aug 23, 2025; Detroit, Michigan, USA; Brooks Koepka of Smash GC plays his shot from the fairway on the sixth hole during the semifinals of the LIV Golf Michigan Team Championship at The Cardinal at Saint John's Resort.
January 13, 2026

PGA Players Support Koepka’s Return: ‘Great Move’

Top players are reacting to the major decision.
Tiger Woods of Jupiter Links answers questions from the media after a TGL match against New York Golf Club at SoFi Center on January 13, 2026, in Palm Beach Gardens, Florida.
January 14, 2026

Tiger Woods Defends Koepka’s Return: ‘A Win for Everyone’

Woods was influential in greenlighting Koepka’s coming back.
Sponsored

ESPN Edge Innovation Conference 2025: Inside the Technology Shaping the Future of..

At ESPN Edge Innovation Conference 2025, ESPN showcased how AI, immersive tech, and a rebuilt direct-to-consumer platform are redefining the future of sports media.
Jan 9, 2026; Los Angeles, California, USA; Los Angeles Lakers forward LeBron James (23) moves the ball against Milwaukee Bucks guard Kevin Porter Jr. (7) during the second half at Crypto.com Arena.
January 12, 2026

LeBron Will Wear Special Jersey Patch for Fanatics Trading Cards

Fanatics Collectibles, which owns Topps, is the NBA’s official trading card licensee.
Brooks Koepka
January 12, 2026

Brooks Koepka Agrees to Give Up Millions for PGA Return

Koepka quit LIV less than three weeks ago.
January 9, 2026

Tigers and Skubal File a Whopping $13 Million Apart on Salary

The ace pitcher is seeking a record-level salary in arbitration.
January 9, 2026

WNBA Union Highlights Big Gap With NBA Health Benefits

WNBA players have far more limited health benefits.