Tuesday, October 20, 2026

Yankees Dragging Feet On $200M-Plus Aaron Judge Extension

  • The three-time All-Star will be a free agent following 2022 season.
  • The sides are $4 million apart in arbitration figures.
Nathan Ray Seebeck-USA TODAY Sports

Want more from Front Office Sports
in your search results?

Add Front Office Sports on Google

Aaron Judge set an Opening Day deadline for a contract extension with the Yankees.

Even with Thursday’s first game against the Red Sox postponed until Friday (12:05 p.m. ET), it doesn’t appear the sides will reach an agreement in time.

For a team that seems perpetually in win-now mode, the Yankees are playing a dangerous game not locking up the face of the franchise.

  • If the 29-year-old doesn’t sign a long-term deal, he’ll head to midseason arbitration to determine a one-year contract. 
  • Judge filed for $21M, while the Yankees countered with $17M, per MLB.com.
  • He received a $1.8M signing bonus as the No. 32 pick in 2013 and since signed six consecutive one-year deals, including one for $10.2M in 2021.
  • He’s a three-time All-Star who finished fourth in 2021 AL MVP voting after slashing .287/.373/.544 with 39 HRs and 98 RBI.

Judge likely wants a six- or seven-year extension north of $200M, which would pass Derek Jeter’s 10-year, $189M deal from 2001 as the Bronx Bombers’ largest. 

The Yankees are never too shy to spend big: They have the third-highest payroll ($240.3M), with ace Gerrit Cole earning $36M per season, MLB’s second-highest AAV (Max Scherzer, $43.3M). 

In the midst of a 12-year title drought, New York should make Judge as comfortable as possible — as soon as possible.

Download the FOS App

The business of sports, in your pocket.

QR code to download the app

Scan the QR code to get the app now.

Linkedin
Whatsapp
Copy Link
Link Copied
Link Copied

What to Read

Brewers Fans Could Find Cheaper World Series Tickets in Tampa

The ticket resale market for the event shows two very different situations.
Oct 19, 2026; St. Petersburg, Florida, USA; Tampa Bay Rays designated hitter Yandy Diaz (2) celebrates with teammates after hitting a two run home run against the Cleveland Guardians during the eighth inning in game six of the ALCS for the 2026 MLB Playoffs at Tropicana Field.

World Series Matchup Highlights Financial Savvy of Brewers, Rays

The two league champions used several shrewd moves to fuel their rise.

Rays Clinch Pennant, Head to Small-Market World Series

The Rays clinched their third American League pennant.
Oct 15, 2026; Los Angeles, California, USA; Milwaukee Brewers players celebrate after winning the NLCS for the 2026 MLB Playoffs against the Los Angeles Dodgers at Uniqlo Field at Dodger Stadium.

World Series Game 1 Tickets Reach Super Bowl Level Prices

Get-in pricing for Friday’s Game 1 is nearing $3,000 per ticket.
podcast thumbnail mobile
Front Office Sports Today

10/20/26 – Knicks’ $4K Opener, Brewers’ $2,800 World Series, Colts Call Peyton?

0:00

Featured Today

Why Europe Is Pumping Out NBA Superstars

The NBA and NCAA have an increasingly European flavor.
October 15, 2026

College Flag Football Is Outgrowing Its DIY Era

Women have been building the college game themselves at the club level.
Oct 5, 2026; Pittsburgh, Pennsylvania, USA; Pittsburgh Penguins general manager Kyle Dubas arrives at the arena before the Penguins host the Winnipeg Jets at PPG Paints Arena
October 12, 2026

NHL’s New Wave of GMs Is Built Different

“I am in the prediction business,” Devils GM Sunny Mehta tells FOS.
Action Images/Peter Cziborra
October 9, 2026

Is Leicester City’s $264 Million Price Tag Too Rich for Hungry Investors?

After falling from grace, how much is a former top club worth?
Oct 3, 2026; Starkville, Mississippi, USA; Alabama Crimson Tide head coach Kalen DeBoer waits to run onto the field prior to the game against the Mississippi State Bulldogs at Davis Wade Stadium at Scott Field. Mandatory Credit: Petre Thomas-Imagn Images
October 7, 2026

Who Is Alabama Football in Year 3 Under Kalen DeBoer?

The No. 6 Crimson Tide host No. 2 Georgia on Saturday.

NFL, Eagles Defend Handling of Jalen Hurts’s Blood Clots

The QB was examined at Cleveland Clinic in London.
Jul 2, 2026; Silvis, Illinois, USA; Blades Brown smiles with his caddie, Brett Swedberg, on the 9th green during the first round of the John Deere Classic golf tournament.
October 15, 2026

Teenage Phenom’s Pro ‘Gamble’ Paid Off With PGA Tour Record

The golfer turned professional in December 2024 when he was 17.
First at FOS
October 20, 2026

Topgolf, John Daly Strike Deal in Wake of Masters Hooters Closure

Daly, 60, last played in the Masters in 2006.
Sponsored

Blake Griffin’s Plan for Media Domination

The former NBA star is building a second act across media & entertainment.
October 15, 2026

Blake Griffin: Clippers Salary Cap Punishment ‘Probably Fits’

Griffin played eight seasons with the Clippers and made five All-Star Games.
October 14, 2026

Rafael Jodar Embroiled in Yet Another Ball Kid Controversy

Jodar told a ball boy to “give me the fucking towel.”
October 13, 2026

MLS Commissioner Don Garber Deflects on Messi Confrontation

Garber called Messi “the GOAT of all GOATs.”
October 8, 2026

Caitlin Clark Wants Mitchell Back With Fever Despite Fan Comments

Mitchell said she has yet to make a decision on her future.