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Divorce on the horizon? Cowboys fail to sign Dak Prescott to long-term deal

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Why a one-year deal could be beneficial for Dak (1:35)

Louis Riddick reacts to the Cowboys' and QB Dak Prescott's failing to reach a long-term deal and explains why a one-year contract could be beneficial for Prescott. (1:35)

Dallas Cowboys owner and general manager Jerry Jones asked this question during negotiations with running back Ezekiel Elliott last summer: "When have I not gotten a deal done?"

The answer is a little different this time around.

Quarterback Dak Prescott's agent Todd France and the Cowboys have been working on a long-term deal for close to 16 months. It was expected to be the richest in Cowboys history and one of the richest in the NFL. Instead, Prescott plans to play the season on the $31.4 million exclusive franchise tag, which he signed June 22.

The sides cannot talk about a long-term deal again until the 2020 season ends, which means the talks are paused and nothing is solved.

There is plenty of blame to go around for the impasse, but know this: This could be the beginning of a slow road to a divorce between the Cowboys and Prescott.

Since the franchise-tag designation has been in use, only two quarterbacks -- Drew Brees in 2005 with the San Diego Chargers and Kirk Cousins in 2016 and 2017 with the Washington Redskins -- played a season under the franchise tag.

The Chargers had Philip Rivers, a first-round pick in 2004 after the Eli Manning trade with the New York Giants, ready to take over. The Redskins never loved Cousins or made him an offer worth accepting, leading to his departure in free agency for the Minnesota Vikings in 2018.

The Cowboys have veteran quarterback Andy Dalton as Prescott's backup on a one-year deal along with Clayton Thorson, who spent last season on the practice squad, and Ben DiNucci, a 2020 seventh-round pick, on the roster.

Most of the recent high-profile quarterback divorces in the NFL have involved veteran quarterbacks hitting the open market. Tom Brady, who turns 43 in August, left the New England Patriots for the Tampa Bay Buccaneers after a 20-year run. Rivers, 38, signed a one-year deal with the Indianapolis Colts in March.

In 2012, Peyton Manning was 36 when he signed with the Denver Broncos after missing the Colts' 2011 season because of a neck injury. The Colts took Andrew Luck with their first overall pick in 2012.

Prescott, who turns 27 on July 29, is entering the prime of his pro career. He has outperformed expectations after being picked in the fourth round of the 2016 NFL draft.

So what happens now?

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What is next for Dak, Cowboys after no new deal is reached?

Adam Schefter explains what the Cowboys and Dak Prescott failing to reach a long-term deal says about the future of both sides.

Jones, the Cowboys' decision-maker, is in an unfamiliar position with his franchise quarterback. This didn't happen with Troy Aikman or Tony Romo. Jones kept both signed to long-term deals with the Cowboys well into their 30s.

Since Aikman, the Cowboys have used a first- or second-round draft pick on a quarterback just once. Quincy Carter, out of the University of Georgia, was a second-round selection (No. 53 overall) in 2001. (The Cowboys used a first-round pick in the 1989 supplemental draft on Steve Walsh.)

The Cowboys did scout the top quarterbacks in the 2016 draft, such as Jared Goff and Carson Wentz. But Jones was upset when Dallas could not trade back into the first round to take Paxton Lynch, whom the Broncos drafted No. 26 overall. Denver released Lynch before the 2018 season.

Prescott must play well in 2020 to earn the megadeal he seeks from the Cowboys or another team if he becomes a free agent. If the Cowboys place the franchise tag on Prescott again 2021, he would earn $37.7 million. And in case you are wondering, the price of a third year on the tag would be $54 million.

Prescott had his best statistical season in 2019 (4,902 yards, 30 touchdown passes) but his worst record (8-8). He has a new coach in Mike McCarthy, and a slightly altered offense to learn. The Cowboys' 2020 schedule is favorable, but there are some difficult defenses on the horizon (Seattle, Pittsburgh, Minnesota, Baltimore, San Francisco) that could challenge Prescott.

Jones was lucky to find Prescott, just as he was lucky to find Romo as an undrafted free agent and lucky to have the No. 1 overall pick in 1989 when he purchased the team and drafted Aikman No. 1 overall.

With how the process has played out, Jones might have to see if he can get lucky again by signing Prescott to a long-term deal this offseason.