Friday, September 18, 2026

Dak Prescott’s Record-Setting Deal

  • Star quarterback Dak Prescott signed a four-year $160 million contract extension with the Dallas Cowboys.
  • The deal includes a $66 million signing bonus, and a record $126 million in guaranteed money.
Joe Nicholson-USA TODAY Sports/Design: Alex Brooks

Even after his 2020 season ended in Week 5 with a gruesome broken ankle, Dak Prescott had tremendous leverage in his negotiations with the Dallas Cowboys. 

On Monday, he used it to break the record for most guaranteed money ever in an NFL contract. The precedent-setting deal could now dictate the future of how the league pays its stars. 

Prescott’s four-year, $160 million contract extension ends a years-long standoff between America’s Team and its franchise quarterback.

  • The contract includes a $66 million signing bonus, which means that Prescott will make a single-season record $75 million in 2021.
  • $126 million is guaranteed at signing — the most ever in NFL history.
  • He will be in line for a new deal at age 31 when the contract expires in 2024.

Players must often choose between long-term security and maximizing their earning power, if they can have either. Prescott — a virtually irreplaceable talent at quarterback — gets both. The Cowboys painted themselves into a corner by not extending Prescott sooner, amplifying his negotiating power, compounded by their 4-7 record after losing him.

The cost of employing a healthy Prescott may be cushioned by a new influx of cash to the NFL. As DEC Management pointed out, billionaire owner Jerry Jones likely knows how much money the league has coming in from its latest round of TV contracts.

Ravens quarterback Lamar Jackson, the 2019 NFL MVP, is sure to have Prescott’s deal in mind as he enters the final year of his rookie contract. Ravens GM Eric DeCosta sought to deflect any comparison between the two young star quarterbacks on Tuesday: “Every negotiation is different. Every player is different. Every GM is different.”

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

Sep 10, 2026; Melbourne, Victoria, Australia; Los Angeles Rams head coach Sean McVay during practice at Marvel Stadium. Mandatory Credit: Kirby Lee-Imagn Images

McVay’s Australia Gripe Highlights NFL’s Business-Football Divide

The Rams coach is looking to forget the team’s struggles in Australia.
Hot & Social/Mets

Sports Teams Are Playing a New Role: Matchmaker

The latest promotion at the stadium? Love.
Sep 17, 2026; Orchard Park, New York, USA; Buffalo Bills wide receiver Joshua Palmer (5) runs to score a touchdown during the first half against the Detroit Lions at New Highmark Stadium. Mandatory Credit: Gregory Fisher-Imagn Images

Bills Mafia Steals the Show in $2.2B Highmark Stadium Debut

The new stadium easily transcended its league-low seating capacity.
Sep 11, 2026; Melbourne, AUS; San Francisco 49ers quarterback Brock Purdy (13) rushes the ball in the second half against the Los Angeles Rams at Melbourne Cricket Ground. Mandatory Credit: Kirby Lee-Imagn Images

NFL Week 1 Ratings Fall 13% Despite New Broadcast Schedule

The league saw a surprisingly sharp drop in viewership.
podcast thumbnail mobile
Front Office Sports Today

NFL Ratings Dip, Steve Belichick Resigns, Knicks Ticket Refunds

0:00

Featured Today

Exclusive

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.
September 4, 2026

Wild Transfer Window Shows How Premier League Towers Over Soccer

Spending in England vastly outstripped the rest of Europe.
Kylian Mbappe On

Mbappé Leaves Nike for On As Brand Launches Soccer Division

Thierry Henry joins as the company’s new director of football.
asset class
September 16, 2026

Ndamukong Suh Says He Almost Invested in the Seahawks

He also “looked at” the Portland Blazers and Thorns.
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.
Sponsored

Drew Weatherford’s Bet on the Youth Sports Economy

Drew Weatherford discusses investing across the youth, college and professional levels.
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.
September 12, 2026

Rybakina Wins First US Open Title, World No. 1, and $5.5M

The 27-year-old will officially become No. 1 in the world on Monday.
September 11, 2026

Taylor Fritz’s Latest Ball Complaint: Retail Ones Are ‘Miserable’

Fritz was knocked out of the US Open in the third round.