• Loading stock data...
Wednesday, September 3, 2025
The biggest names in sports media. All in one room. Get your ticket now!

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

Oct 13, 2024; Philadelphia, Pennsylvania, USA; Philadelphia Eagles quarterback Jalen Hurts (1) and wide receiver A.J. Brown (11) celebrate their touchdown pass during the second quarter against the Cleveland Browns at Lincoln Financial Field.

TV Ratings Just Changed Again. The NFL Will Be the Big Winner

Nielsen’s new viewership system will have a big impact on sports.

MLB Extends Leaves of Clase, Ortiz as Betting Probe Continues

Their paid non-disciplinary leaves have been extended “until further notice.”
Ohio State Buckeyes wide receiver Jeremiah Smith (4) celebrates with offensive lineman Donovan Jackson (74) after a touchdown catch against Notre Dame Fighting Irish in the first quarter during the College Football Playoff National Championship at Mercedes-Benz Stadium in Atlanta on January 20, 2025.

The Most Expensive Roster Year in College Football History

The House settlement created revenue-sharing—and a big NIL loophole.
Mar 12, 2024; Phoenix, Arizona, USA; Los Angeles Dodgers designated hitter Shohei Ohtani talks with translator Ippei Mizuhara in the dugout against the San Francisco Giants during a spring training baseball game at Camelback Ranch-Glendale.

Bookie Believes Shohei Ohtani ‘Was Aware’ of Interpreter’s Gambling

Mathew Bowyer ran the illegal gambling business used by interpreter Ippei Mizuhara.

Featured Today

‘You’re Going to Get Beat Up’: The Liberty’s All-Male Practice Squad

A select group suits up weekly to take on the defending champs.
August 24, 2025

The Honey Deuce Effect: How Tennis Perfected the Signature Cocktail

Sold every 1.5 seconds, they total more than $12 million in sales.
Dec 21, 2024; Austin, Texas, USA; Texas Longhorns quarterback Arch Manning (16) warms up as the Texas Longhorns prepare to play the Clemson Tigers in the first round of the College Football Playoffs at Darrell K Royal Texas Memorial Stadium.
August 23, 2025

Schools Are Hesitant to Allow PE Into Their Athletic Departments

Regardless of budget, schools don’t believe the risk is worth the reward.
Oct 2, 2024; Rosemont, IL, USA; Big Ten commissioner Tony Petitti speaks with the media during the 2024 Big Ten Women’s Basketball media day at Donald E. Stephens Convention Center.
August 22, 2025

‘Not Ready to Jump In’: Power 4 Commissioners Aren’t Sold on PE

Top leaders in college sports have yet to see a satisfactory proposal.

No American Men in US Open Semifinals After 2024 Breakthrough

Two American men played in the semifinals last year.
Aug 6, 2025; Los Angeles, California, USA; Son Heung-min poses during an LAFC introductory press conference at BMO Stadium
August 31, 2025

Son Heung-Min Effect Will Hit Big for MLS and L.A.

With a record signing, the South Korean supernova has landed at LAFC.
September 1, 2025

Gareth Bale: MLS Quality Hurt By Low Salaries

Bale said MLS salaries aren’t competitive enough to lure stars from Europe.
Sponsored

Gareth Bale on MLS vs EPL, Retirement & Buying Cardiff City

Gareth Bale shares his post-soccer business playbook.
Candace Parker
August 29, 2025

Candace Parker Not a WNBA Owner Yet, but Her Business Is Booming

Her WNBA peers say she made the blueprint for earning off the court.
August 29, 2025

Cowboys’ Parsons Approach Shows High Cost of Delayed Contracts

Parsons will sign a four-year, $188 million deal with the Packers.
August 29, 2025

Kyle Schwarber’s MVP Candidacy Could Lead to Massive Payday

The Phillies slugger makes history and could do so again this winter.
Cooper Lutkenhaus
August 28, 2025

Running Prodigy Ditches High School and College for Nike at 16

Cooper Lutkenhaus is a contender at next month’s track world championships.