The two sides failed to reach a long-term agreement Wednesday, and Prescott heads into 2020 on the franchise tag. Recent history suggests Prescott is making a good bet on himself—but the league is also facing uncertain times.

As the clock struck 4 p.m. ET on Wednesday, many NFL teams and players hit a point of no return. The deadline for franchise-tagged players to sign new deals passed with most tendered players not reaching long-term agreements with their team. With the exception of Chiefs defensive tackle Chris Jones and Titans running back Derrick Henry, who reached last-minute deals with their respective teams, 13 players who received the franchise tag earlier in the offseason will have to wait until 2021 to restart any negotiations. The most important and intriguing sides who failed to agree to new terms: the Cowboys and quarterback Dak Prescott.

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Prescott and Dallas haven’t reportedly held “substantive” contract discussions since March. The two sides are hung up on the length of a potential contract. Dallas reportedly offered a five-year deal that averaged $34.5 million per year and guaranteed $110 million. Prescott wants a four-year pact. He signed his exclusive franchise tender in late June and is now scheduled to make $31.4 million this season after playing four years under his rookie contract, which paid him $2.7 million total. That’s a hefty pay raise, but the former fourth-round pick is aiming for more. It’s a gamble—for both sides.

For Prescott, recent history suggests that it’s worth the risk. The Cowboys need Prescott to guide their offense much more than Prescott needs the Cowboys to get the money he desires. Had Prescott reached a four-year deal, he’d enter free agency at 30 years old, presumably with a chance at earning one more big-money contract. As The Ringer’s Danny Heifetz has noted, the NFL salary cap has increased by nearly 40 percent across the past six seasons and could reach $275 million five years from now. The $34.5 million Dallas offered would be peanuts for a franchise quarterback by then, but a shorter deal would allow Prescott to cash in sooner.

Prescott’s decision to play on the tag, though, is a major risk. COVID-19’s impact on the league budget is still unclear. The salary cap could dip if there are no fans in the stands this season, and the NFL is reportedly already discussing ways to spread out that cap hit, if possible. There may not even be $34.5 million on the table for Dak in 2021. 

The Cowboys’ proposed deal would have locked up their franchise quarterback through what could be the prime of his career, surrounded by what’s currently one of the most talented rosters in the league. Having Prescott’s contract settled would also allow the team to prioritize maintaining its core as the squad pushes for a Super Bowl under new coach Mike McCarthy. Instead, Dallas is guaranteed only one more year of Prescott before they do this song and dance all over again.

Quarterback deals typically reset the market, but the Cowboys’ offer would have put Prescott third behind the Seahawks’ Russell Wilson ($35 million per year) in average value and equal with the Rams’ Jared Goff ($110 million guaranteed) in guaranteed money. Of course, the Chiefs’ Patrick Mahomes just obliterated the market when he agreed to his colossal 10-year, $450 million deal. And while Prescott won’t sign that spectacular of a deal, Prescott and his representatives surely expect the two-time Pro Bowler to sign a deal that exceeds the value of those signed by Wilson and Goff.

Prescott has reason to believe he’s worth every penny, too. He enters his age-27 season coming off one of his best statistical performances. He tossed a career-high 30 touchdowns, set a career best in yards per attempt (8.2), ranked fourth in QBR, and finished first in defensive-adjusted yards above replacement (DYAR), a metric that measures a quarterback’s value, according to Football Outsiders. Through four seasons, Prescott has led the Cowboys to two NFC East crowns. Last year, he arguably played at an MVP-caliber level through stretches, so his worth to Dallas’s offense shouldn’t go understated. Some fans believe Prescott benefits immensely from the talent around him, but there’s little reason to believe he could be easily replaced.

Franchise quarterbacks do not, sadly, grow on trees. The Cowboys signed former Bengals quarterback Andy Dalton on a one-year deal to serve as their backup, but the 32-year-old has been on the back end of his career for a few years now. Currently, the 2021 free agency QB class is light on prominent names under 30 (Mitchell Trubisky, Jameis Winston, Jacoby Brissett). The Cowboys don’t anticipate a high enough selection in the 2021 draft to select Clemson’s Trevor Lawrence, Ohio State’s Justin Field, or any other marquee QB prospect.

If the two sides fail to once again agree to a new deal in 2021, Dallas could again tag Prescott next offseason. He’d be owed $38 million under the tag next year, pushing his earnings to nearly $70 million across a two-year span. If he were to get tagged for a third consecutive year, he’s projected to earn $54 million—a virtually untenable amount for the Cowboys. Maybe that’s why Vikings quarterback Kirk Cousins—who earned $44 million after getting tagged twice by Washington and made more cash than any player in the NFL between 2016-20—told Prescott “don’t be afraid of the tag”. Washington let Cousins go after the 2017 season. Since then, Washington has restarted a search for its long-term quarterback and is hoping that 2019 first-round pick Dwayne Haskins is the future at the position. Cousins signed a fully guaranteed three-year, $84 million contract with Minnesota—the first fully guaranteed contract in NFL history and, at the time, the highest-paying contract.

Precedent suggests that Prescott will get the money he’s looking for. As his brother, Tad, suggested on Twitter, it’s unclear whether that will be in Dallas. The Cowboys had the leverage in 2019 when star running back Ezekiel Elliott held out of training camp before agreeing to a six-year, $90 million extension. But this time, Dallas doesn’t hold the cards. Mahomes’s contract helps Prescott’s case only as far as his market value is concerned. Heck, the fact that Prescott would be due to earn only the same amount of guarantees as Goff, the no. 1 pick of the same draft class who has underperformed Prescott, suggests that Prescott is right to pursue a larger contract. Carson Wentz, the no. 2 pick in that draft, has already cashed in on an extension, too.

The longer Dallas waits, the more money it will likely have to pay Prescott. Sure, Prescott is gambling with his health and against what is currently an uncertain salary cap landscape, but it appears to be a risk worth taking.

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