With Dak Prescott's extension, Cowboys legacy is on the line

FRISCO, Texas -- Now that Dak Prescott has signed another mega-contract to be the Dallas Cowboys ' starting quarterback, however many years he has left will be about legacy.

He has his money. Before signing the most recent deal, he cashed in more than $160 million, with a little more than $4 million on his rookie deal (2016-19), $31.4 million on the franchise tag in 2020, and $126 million from 2021 to 2023. And he can earn $240 million on his latest deal, according to ESPN's Adam Schefter .

But in order for Prescott to move from a very good statistical quarterback to one of the best in Cowboys history, he has to do something he has not done yet: get to a Super Bowl. Maybe even win it.

It is not entirely fair, but those are the standards in Dallas set by Hall of Famers Roger Staubach and Troy Aikman .

Prescott has done just about everything else in his first eight years as the starting quarterback. He has set the team record for touchdown passes in a season (37). By the end of next season, he should surpass Tony Romo (34,183) as the franchise leader in passing yards. He is 45 touchdown passes shy of Romo's record (247). He has won the NFC East four times. He has been to the Pro Bowl. In 2023, he had his best season and was named All-Pro and finished second in MVP voting. He was named the winner of the Walter Payton Man of the Year award.

But he has not gotten past the second round of the playoffs, and the stench from the wild-card loss to the Green Bay Packers in January still hangs over the entire organization.

To do what he's not done yet, Prescott could be asked to do more with less -- in part, because of his contract, although the Cowboys were able to sign CeeDee Lamb to a four-year contract extension on Aug. 26.

Teams with high-priced quarterbacks -- such as Buffalo's Josh Allen , Kansas City's Patrick Mahomes , Cincinnati's Joe Burrow and the Chargers' Justin Herbert -- have had to make business decisions at other positions.

The Cowboys initially asked Prescott to do more with less in 2018 without a true No. 1 receiver, and when that did not work out, they traded for wide receiver Amari Cooper , giving up a first-round pick to the Raiders.

Entering his ninth season, Prescott is a different quarterback than he was when entering his third. He understands the game more. He understands his game more. He understands defenses more.

In 2024, he'll need to be better than he has been, as the Cowboys move to a running-back-by-committee approach and the may start two rookies on the offensive line. He needs to be better while facing a schedule that features seven games versus 2023 playoff teams in the first 11 weeks.

After this season, the Cowboys could look completely different.

This could be the final years of franchise stalwarts guard Zack Martin , a future Hall of Famer, and defensive end DeMarcus Lawrence . If they both depart after this season, Prescott will be the longest-tenured Cowboy, since fellow 2016 draft pick Ezekiel Elliott took a one-year hiatus from Dallas in 2023 for a stint with the New England Patriots .

This offseason, the Cowboys said goodbye to left tackle Tyron Smith , a future Hall of Famer, center Tyler Biadasz , running back Tony Pollard and defensive end Dorance Armstrong , among others, as Dallas prepped for deals with Prescott, CeeDee Lamb and Micah Parsons . The only notable additions were bringing back Elliott and linebacker Eric Kendricks in free agency, as Jerry Jones' definition of 'all-in' seemed to be different than what many others thought.

But Jones is no doubt all-in on Prescott now, even if it took some negotiating time to get there.

If Prescott, entering his ninth season, plays out the deal, he will be the longest-tenured starting quarterback in franchise history. Aikman was the Cowboys' starter for 12 seasons, Romo started for nine and Staubach for eight.

Since 1980, the only quarterback to wait longer to go to a Super Bowl for the first time with the club that drafted him was Ken Anderson, who was in his 10th season as Cincinnati's full-time starter. Matt Ryan and Peyton Manning went to their first Super Bowls with Atlanta and Indianapolis, respectively, in their ninth seasons as the full-time starters.

That's the challenge Prescott faces in defining his legacy on the field.