Thursday, April 16, 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.

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

Jan 10, 2026; Chicago, IL, USA; Green Bay Packers wide receiver Matthew Golden (0) scores a touchdown against the Chicago Bears during the second half of an NFC Wild Card Round game at Soldier Field.

Efforts to Fight Sports Streaming Fragmentation Ramp Up in D.C.

“It’s not only confusing, it’s also damn expensive.”
Apr 11, 2026; Philadelphia, Pennsylvania, USA; Philadelphia Phillies infielder Alec Bohm (28) throws to first against the Arizona Diamondbacks in the second inning at Citizens Bank Park.

Alec Bohm’s Family Feud Heats Up As Parents Push Back

The third baseman claims his parents took advantage of him.
Apr 10, 2026; Kansas City, Missouri, USA; Kansas City Royals shortstop Bobby Witt Jr. (7) throws to first base during the seventh inning against the Chicago White Sox at Kauffman Stadium.

Royals One Step Closer to New Kansas City Stadium

The MLB club receives support from two key votes.
Apr 8, 2026; Boston, Massachusetts, USA; Boston Red Sox right fielder Wilyer Abreu (52) hits a single against the Milwaukee Brewers during the seventh inning at Fenway Park.

Red Sox Say Fans Whiffed With ‘Junk Fees’ Lawsuit

“Plaintiffs were not deceived,” the team argues in a new filing.

Featured Today

blake griffin

Inside Blake Griffin’s Rookie Season at Prime Video

The six-time All-Star was initially hesitant to enter the media space.
Matthew Schaefer/Front Office Sports
April 10, 2026

Matthew Schaefer Has the Hockey World in His Thrall

The teenage Islanders defenseman cannon-balled into the NHL.
April 9, 2026

College Athletes Are Ignoring NCAA Gambling Bans

“We were going to bet regardless,” says one former D-I athlete.
April 8, 2026

Why Did FIFA Do a Deal With an Obscure Prediction Market?

The product is scheduled to launch on Thursday.

French Open Will Allow Wearables Like Whoop on ‘Trial Basis’

The trial will extend to the US Open and Wimbledon.
Jan 13, 2026; San Francisco, California, USA; Golden State Warriors guard Stephen Curry (30) looks to shoot a jump shot against the Portland Trail Blazers in the third quarter at Chase Center.
April 14, 2026

Steph Curry Auctions 75 Pairs of Shoes As Sneaker Free Agency Looms

Sneakers Curry wore to a 2010 game are going for more than $50,000.
April 15, 2026

Sophia Wilson on Returning to Soccer With a Million-Dollar Deal

Wilson became the NWSL’s first million-dollar player this offseason.
Sponsored

From Gold Medalist to Business Founder

Allyson Felix on investing in women’s sports and what comes next for track & LA28.
April 14, 2026

Valkyries GM Avoids Questions After Draft Trade: ‘I’m Exhausted’

Golden State traded Flau’jae Johnson to Seattle for two second-rounders.
April 13, 2026

Azzi Fudd Gets $500K Salary As WNBA No. 1 Pick

The new CBA sets a $500,000 salary for the first pick.
April 13, 2026

Carlos Alcaraz Cracks Top 4 in Career Earnings Despite Loss

Jannik Sinner reclaimed the world No. 1 ranking. 
April 10, 2026

WNBA Free Agency Tracker: Welcome to the Million-Dollar Era

The supermax deal is worth $1.4 million per year.