Wednesday, September 23, 2026
  • -
    days
  • -
    hours
  • -
    minutes
  • -
    seconds

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.

This field is for validation purposes and should be left unchanged.

Sign up for
The Memo Newsletter

Get the biggest stories and best analysis on the business of sports delivered to your inbox twice every weekday and twice on weekends.

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.
Linkedin
Whatsapp
Copy Link
Link Copied
Link Copied

What to Read

MLB Raises PE Ownership Limit to 20%

The change happened earlier this summer and wasn’t announced.

Ohtani Return Gives MLB, Fox a Boost; Judge Heads to IL

The two MLB superstars reverse their roster status from two weeks ago.
Jul 18, 2026; Boston, Massachusetts, USA; The Boston Red Sox ground crew remove the field tarp after a rain delay before a game against the Tampa Bay Rays at Fenway Park. Mandatory Credit: Eric Canha-Imagn Images

Incoming Nor’easter Could Scramble MLB’s Playoff Seeding Picture

A brutal weather forecast looms over this weekend’s Chicago-Boston series.
Sep 19, 2026; St. Petersburg, Florida, USA; Boston Red Sox third baseman Caleb Durbin (5) tags out Tampa Bay Rays center fielder Cedric Mullins (31) as he attempted to steal during the third inning at Tropicana Field. Mandatory Credit: Kim Klement Neitzel-Imagn Images

MLB’s Fixed Bracket Could Punish the AL’s Best Teams

The league’s postseason format is generating a fresh round of controversy.
podcast thumbnail mobile
Front Office Sports Today

9/23/26 – NFL QB Injuries Pile Up, Seahawks’ Scouting Cold War, Aikman’s Contract Limbo

0:00

Featured Today

Hot & Social/Mets

Sports Teams Are Playing a New Role: Matchmaker

The latest promotion at the stadium? Love.
Exclusive
September 18, 2026

Vicious Infighting Is Jeopardizing the Future of Women’s Baseball

The WPBL’s own CEO admits there’s a “power struggle.”
September 17, 2026

Fantasy Football Drafts Are Turning Into Full-Blown Vacations

Leagues are forgoing solo drafts and replacing them with in-person getaways.
Oct 4, 2025; Tempe, AZ, USA; General action during the first period of the game between the Arizona State Sun Devils and the Penn State Nittany Lions at Mullett Arena
September 10, 2026

How Military-Style Workouts in College Sports Get Dangerous

For elite athletes, high-intensity training can be “very appealing.”
September 6, 2026

Is Carolyn Tisch Blodgett the Future Face of Giants Ownership?

Amid changes at top of Giants ownership, eyes are on Tisch Blodgett.

Why Kerri Walsh Jennings Picked a Side in the Volleyball War

The Olympian co-owns the expansion team NorCal Rumble.
Kylian Mbappe On
September 18, 2026

Mbappé Leaves Nike for On As Brand Launches Soccer Division

Thierry Henry joins as the company’s new director of football.
September 21, 2026

Presidents Cup International Team Wants ‘Separation’ From PGA Tour

The U.S. leads the Presidents Cup 13-1-1 all-time.
Sponsored

How Ryan Smith Is Building the Future of Sports in Utah

Utah Jazz and Mammoth owner talks from tech to team ownership.
Jul 15, 2026; New York, NY, USA; Kevin Hart arrives on the red carpet before the 2026 ESPY Awards at Lincoln Center.
September 17, 2026

LeBron James and Kevin Hart Planning YouTube Golf Collab

Both celebrities recently launched golf content channels.
asset class
September 16, 2026

Ndamukong Suh Says He Almost Invested in the Seahawks

He also “looked at” the Portland Blazers and Thorns.
Aug 28, 2026; Kansas City, Missouri, USA; Kansas City Chiefs quarterback Patrick Mahomes (15) warms up against the Seattle Seahawks prior to a game at Arrowhead Stadium.
September 14, 2026

Mahomes Comeback Kicks Off ESPN ‘MNF’ Coverage

The two-time NFL MVP is completing a remarkable injury recovery.
September 13, 2026

Myles Garrett’s Knee Surgery Adds to Rams’ Early Woes

He’ll miss at least four games on IR.