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Conventional wisdom suggested the Dallas Cowboys would get a done deal with quarterback Dak Prescott early this offseason. The 2023 NFL MVP runner-up's $59.455 million 2024 salary cap number was thought to be untenable. Equally important, Prescott has provisions in his contract preventing Dallas from designating him as a franchise or transition player in 2025 should he play out the four-year, $160 million deal he signed in 2021 and a no-trade clause. Instead, the Cowboys did a small contract restructure to lower Prescott's 2024 cap number to $55.455 million.

Negotiations have moved at a snail's pace despite Cowboys owner Jerry Jones recently stating he wants to keep Prescott. There reportedly have not been any substantive contract discussions. Jones also said he would like to see "more leaves fall." One of the leaves to fall a couple of weeks ago was Jared Goff. The Detroit Lions signed their quarterback to a four-year, $212 million contract extension, making Goff the NFL's second-highest-paid player at $53 million per year.

The Cowboys' current predicament with Prescott could have been avoided by taking a more proactive approach to his veteran contract negotiations like the Philadelphia Eagles, their NFC East rival. Philadelphia began a practice of locking up core players well in advance of free agency during Joe Banner's tenure as team president, which included the Eagles advancing to five NFC Championships and one Super Bowl in an eight-year span during the 2000s. It has continued under executive vice president/general manager Howie Roseman, who has seen the Eagles win Super Bowl LII and get back to the Super Bowl five years later while guiding the front office. 

Extending Prescott's rookie contract

The Cowboys would have needed to make Prescott the top signing priority along with or instead of edge rusher DeMarcus Lawrence, who was given a franchise tag for a second straight year in 2019 when he was scheduled to make $2.025 million during the final year of his rookie contract. Lawrence became the third member of the $20 million-per-year non-quarterback club to join Khalil Mack and Aaron Donald in early April 2019. 

The Lions are evidence that a team can negotiate two high-end contracts simultaneously. Wide receiver Amon-Ra St. Brown and offensive tackle Penei Sewell each became the highest-paid player at their respective positions this year in late April a day before the NFL Draft began.

Heading into the 2019 offseason, Aaron Rodgers was the NFL's highest-paid player at $33.5 million per year. He received a four-year, $134 million extension worth a maximum of $138 million through salary escalators and incentives from the Green Bay Packers during the 2018 preseason. The deal had $98.2 million in guarantees, of which $78.7 million was fully guaranteed at signing.

The $30 million-per-year barrier had been hit a couple of months earlier when Matt Ryan received a five-year, $150 million extension from the Atlanta Falcons. Ryan's deal contained NFL records of $100 million in overall guarantees and $94.5 million fully guaranteed at signing.

Kirk Cousins was third in the NFL salary hierarchy. The Minnesota Vikings signed Cousins to a fully guaranteed three-year, $84 million deal (worth a maximum of $90 million through incentives), which at the time made him the league's highest-paid player, in 2018 free agency that March.

Prescott ended the 2018 season on a high note. He took a major step forward over the second half of the season, which coincided with the Cowboys acquiring wide receiver Amari Cooper from the Oakland (now Las Vegas) Raiders as the late October trading deadline approached. Prescott completed 71.6% of his passes for 2,225 yards with 12 touchdowns and three interceptions to post a 103.4 passer rating while the Cowboys went 7-1 to win the NFC East. The Cowboys were eliminated in the divisional playoffs by the Los Angeles Rams, the eventual NFC champions, after beating the Seattle Seahawks in a wild-card playoff game.

Only Tom Brady, who is now considered the greatest quarterback of all time, had more than Prescott's 32 regular-season wins since he entered the NFL in 2016. Prescott's 14 game-winning drives are still the most in league history during a quarterback's first three NFL seasons. Jones didn't do himself any favors when he inexplicably proclaimed prior to a mid-November game against the Falcons during the 2018 season that he wouldn't consider trading Prescott for two first-round picks even if the top spot in the 2019 NFL Draft was included.

It probably would have required making Prescott the NFL's second-highest-paid player in order to get a deal done at the same time as Lawrence's. The Cowboys would have also needed to concede on contract length with a four-year extension. The continued insistence on a fifth new contract year was an impediment to a Prescott deal before he actually signed long term in 2021.

A four-year, $124 million extension, averaging $31 million per year, would have been in line with the average of the league's three highest-paid players (Rodgers, Ryan and Cousins) at the time. Their contracts averaged $30,666,667 per year. The average length of these deals was four new years. 

Prescott's contract security likely would have needed to be consistent with the average of just over $94 million in guarantees where a little more than $85.5 million was fully guaranteed at signing for these three deals. The nearly $9.5 million in cap relief the Cowboys got from signing Lawrence could have come in handy for a Prescott deal.

Prescott would have been signed before Russell Wilson reset the quarterback market a little more than a week later at $35 million per year. The Seahawks gave Wilson a four-year, $140 million extension with a maximum value of $146 million because of salary escalators. Wilson's contract had $107 million in guarantees, which was the most ever for an NFL player at that time. The Pittsburgh Steelers quickly signed 37-year-old Ben Roethlisberger a two-year, $68 million extension, averaging $34 million per year shortly thereafter.

A second Prescott contract extension

A four-year extension in 2019 would have made 2023 Prescott's contract year. Prescott was coming off a down year by his standards. He uncharacteristically led the NFL with a career-high 15 interceptions in 2022 despite missing five games early in the season with a fractured right thumb. 

The Cowboys were second in the NFC East in 2022 with a 12-5 record. A wild-card playoff game was won against the Tampa Bay Buccaneers before losing to the San Francisco 49ers in the divisional playoffs. The Cowboys would have needed to put Prescott near the top of the quarterback market even though 2022 wasn't one of his best seasons for an extension to take place again in the early part of April. 

The 10-year, $450 million extension worth up to $475 million with incentives, averaging $45 million per year, Patrick Mahomes signed with the Kansas City Chiefs in June 2020 served as ceiling for quarterback salaries until the 2022 offseason. Rodgers reset the pay scale for quarterbacks in March 2022 by becoming the NFL's first $50 million-per-year player. The Packers signed Rodgers to a contract widely considered to be $150.815 million over three years, averaging $50,271,667 per year, although there were two additional below-market years (2025 and 2026) in the deal. New benchmarks for guaranteed money in football contracts with $150.665 million in total guarantees and $101.515 million fully guaranteed at signing were established.

Players started routinely signing for more than Mahomes after the Rodgers deal. Nobody expected Deshaun Watson to get a fully guaranteed five-year, $230 million contract, averaging $46 million per year, as a part of his trade from the Houston Texans to the Cleveland Browns a couple of weeks later, considering he had four years worth $136 million remaining on the four-year contract extension he previously signed in September 2020. 

Kyler Murray signed a five-year, $230.5 million extension (worth up to $238 million through salary escalators), averaging $46.1 million per year, with the Arizona Cardinals in July 2022 at the start of training camp. The deal has $160 million in overall guarantees where $103.3 million was fully guaranteed at signing. An additional $29.5 million in latter years of Murray's contract, which isn't guaranteed for injury at signing, can also become completely secure to bring the total amount that can be guaranteed to $189.5 million.

Wilson received a five-year, $245 million extension, averaging $49 million per year, from the Denver Broncos in early September several days before the 2022 regular season began. His deal contained $165 million in guarantees with $124 million fully guaranteed at signing, which was the second most ever in an NFL contract at the time.

The emerging trend of quarterbacks giving up five new years with extensions (Murray and Wilson) would have given the Cowboys more ammunition to get the same length. The Wilson contract likely would have been an important data point in 2023 negotiations. Wilson having the worst season of his 11-year NFL career in 2022 along with the Cowboys getting an extra year this time around may have been enough for Prescott to join Rodgers in the $50 million-per-year club. Based on Wilson's deal, a five-year, $250 million extension with $175 million in overall guarantees, where $125 million was fully guaranteed at signing, could have been reasonably expected.

The Cowboys wouldn't have been contending with trying to negotiate Prescott's deal after Jalen Hurts and Lamar Jackson both eclipsed Rodgers' $50,271,667 average yearly salary. The Eagles signed Hurts to a five-year, $255 million extension, averaging $51 million per year, during the latter part of April. The deal is worth as much as $270 million because of salary escalators. There are $180 million in overall guarantees, of which $110 million was fully guaranteed at signing.

The ink was barely dry on Hurts' contract before Jackson and the Baltimore Ravens agreed to a five-year, $260 million deal, averaging $52 million per year, shortly before the start of the 2023 NFL Draft. Jackson has $185 million of overall guarantees in the contract where $135 million was fully guaranteed.

Final thoughts

The Cowboys missed the opportunity to sign Prescott for nearly $10 million per year cheaper two years earlier with their actual approach to contract extensions. Prescott could have been signed to a third contract most likely through the 2028 season with Dallas continually being proactive. 

Prescott on a $50 million-per-year deal would be a good value given how the quarterback market has continued to develop and the type of season he had in 2023. Justin Herbert replaced Jackson as the league's highest-paid player last July at the start of training camp. The Los Angeles Chargers gave Herbert a five-year, $262.5 million extension, averaging $52.5 million per year. The extension's maximum value is $267.5 million because of $2.5 million of base salary escalators each in 2028 and 2029.

Herbert's deal has $193,738,375 in guarantees, of which $133,738,375 is fully guaranteed at signing. The total amount that can become guaranteed is $218,738,375. That's because $25 million of Herbert's unsecured $47 million 2028 base salary is guaranteed for injury on the third day of the 2026 league year (mid-March 2026). The $25 million becomes fully guaranteed on the third day of the 2027 league year (mid-March 2027).

Joe Burrow is the current NFL salary standard bearer. He signed a five-year, $275 million extension, averaging $55 million per year, with the Cincinnati Bengals last September right before the start of the 2023 regular season. The deal is worth up to $281.25 million thanks to $1.25 million of annual incentives in the extension years (2025 through 2029). Burrow has $219.01 million of salary guarantees in which $146.51 million was fully guaranteed at signing.

In addition to being the NFL MVP runner-up, Prescott earned Second Team All-Pro honors for the first time in his eight NFL seasons because he had a career year. He posted career highs in completion percentage (69.5%) and passer rating (105.9). A league-leading 36 touchdown passes and 4,516 passing yards were the second-best marks of Prescott's career.

Prescott would be the league's sixth-highest-paid player with the 2023 extension. By the time the 2024 regular season starts, Prescott could have dropped to ninth on the NFL salary totem pole. Jordan Love, Trevor Lawrence and Tua Tagovailoa are in line for new deals, respectively, from the Packers, Jacksonville Jaguars and Miami Dolphins that are expected to exceed $50 million per year.

It's conceivable that Prescott, who turns 31 in July, will become the NFL's first $60 million-per-year player if the Cowboys make a serious attempt to extend his contract given the dynamics surrounding a potential negotiation. At least $150 million fully guaranteed at signing and more than Watson's $230 million in total guarantees might be a necessity to consummate a deal.

Some of Prescott's comments suggest that he is comfortable playing out his contract and testing free agency in 2025. A healthy Pro Bowl-caliber quarterback in his prime hitting the open market would be unprecedented. If that comes to fruition, the Cowboys will have nobody to blame but themselves because of their preference for waiting to do contract extensions.