It is not just because the Philadelphia Eagles just won Super Bowl LII. As much as that should peeve the Cowboys, they need to win now because, yes, it's been 22 seasons since their last Super Bowl but also because of Prescott's current contract.
One of the benefits of having Prescott as the starter is that he is on his rookie contract. He will count roughly $726,000 against the salary cap in 2018. Theoretically, the Cowboys should be able to take care of other players, like Zack Martin and DeMarcus Lawrence, and pursue quality free agents with Prescott on his rookie deal.
In the not-too-distant future, the Cowboys will have to make a decision on Prescott's future with the quarterback money reaching astronomical levels.
Last week the San Francisco 49ers gave Jimmy Garoppolo -- who has seven career starts -- a five-year contract worth $137.5 million. Kirk Cousins could get more on a yearly average than that by next month as an unrestricted free agent.
Quarterbacks always take up an inordinate amount of salary-cap space. It speaks to the importance of the position and the lack of quality quarterbacks to go around. For years, former Cowboys quarterback Tony Romo's cap figure dominated the team's balance sheet. Last year, Romo counted $10.7 million against the cap and he wasn't even on the roster. This year, Romo will count $8.9 million against it, and it will be his second year of not playing.
The Cowboys can't sign Prescott to a multi-year extension until after the 2018 season, per league rules. After excelling as a rookie (23 touchdown passes, four interceptions) in 2016, Prescott was not as successful in 2017 (22 touchdowns, 13 interceptions) and the Cowboys missed the playoffs with a 9-7 record.
For Prescott, finding that 2016 form is imperative from a team perspective but also from an individual standpoint.
If he does not show the form he had as a rookie, will the Cowboys commit to him with a long-term deal after 2018? If he has similar statistics, whether the Cowboys make the postseason or not, the club can just let him play out the final year of his contract.
That would open up the possibility of using the franchise tag on him in 2020 if they can't reach a long-term deal. The Washington Redskins went down that road with Cousins, using the franchise tag on him in back-to-back years because they liked him but they did not love him enough to commit the megabucks.
The Redskins and Kansas City Chiefs agreed to a trade involving Alex Smith, who will receive a four-year, $94 million extension from Washington that includes $71 million in guarantees. Free to hit the market, Cousins could end up with a deal that pays him upward of $30 million a season from a quarterback-needy team like the New York Jets, who have a ton of cap room.
In 2007, the Cowboys signed Romo to a six-year contract worth $67.5 million after he started just 17 games. In 2018, Garoppolo has a contract worth nearly double that after just his seven starts.
Prescott has guided the Cowboys to a playoff spot. He has won 22 of his 32 regular-season starts. He has back-to-back 3,000-yard passing seasons. By the time the Cowboys can approach him about a long-term deal, he could have 48 starts to his credit with a resume that certainly would eclipse Garoppolo's at the time he re-signed with San Francisco.
The Cowboys' decision with Prescott will affect the franchise for years to come. Provided he plays well in 2018, he will command a contract that is likely more than his actual worth. Teams have had to commit close to $100 million for quarterbacks like Andy Dalton and Ryan Tannehill, despite neither having playoff success, because that is the going rate.
As the prices rise, the Cowboys will have to make a decision on Prescott when they might not want to make it. If they commit to him long-term, they will find themselves in the same predicament as the Romo contract, restructuring the deal almost yearly to either get under the cap or create room to add players. If they don't make the commitment, then they will have to pay the hefty price of a franchise tag knowing the chances of a long-term relationship will be as likely as one between Cousins and the Redskins.
The Seattle Seahawks won a Super Bowl with Russell Wilson on his rookie contract. They were able to lock down key pieces defensively before they had to fork over $87.6 million to Wilson on a four-year deal that included a $31 million signing bonus in 2015.
These windows of opportunity that are often mentioned do not stay open for long.
The Cowboys and Prescott must win now, as in 2018.