The Cowboys' salary-cap mismanagement is wasting Dak Prescott

Under Romo's original extension, the Cowboys could have cut Romo and paid just $5 million in dead money. Because they repeatedly restructured Romo's deal, though, they instead owed $19.6 million in accounting charges. Dallas used the post-June 1 exception to spread those charges over two years, paying $10.7 million in 2017 and $8.9 million this season. Romo has played four games over the past three seasons, and the Cowboys will have paid him more than $40 million in cap charges. If Prescott stays healthy this season, he'll play 48 games over that same time frame and cost a fraction over $2 million.

The Cowboys' other cap issues

Romo wasn't the only player responsible for dead money on the Cowboys' cap. While he cost $10.7 million in 2017, Dallas also devoted an additional $15.9 million in dead money to a bevy of other players. The most notable deals were to free-agent missteps Cedric Thornton ($3.5 million) and Carroll ($2 million) as well as longtime Cowboys Brandon Carr ($2.7 million) and Doug Free ($2.5 million). Both Carr and Free had restructured their contracts once to create cap space; by 2017, Carr was on the Ravens, and Free had retired.

This year, Romo's $8.9 million hold amounts to less than one-third of the dead money on Dallas' books. The Cowboys are responsible for $8 million after cutting Bryant, which represents one of the rare Dallas extensions that didn't involve any restructuring. The $8 million amounts to two years of accelerated signing bonus. Thornton and Carroll are back for a combined $4.5 million. Deonte Thompson, who signed a deal with a $1 million signing bonus in March, was cut before the season before re-signing. Benson Mayowa is also on the books for $1.1 million in dead money.

The two other veteran Cowboys on long-term deals who were released this offseason were Orlando Scandrick ($2.3 million in dead money) and Dan Bailey ($800,000). Scandrick has his deal restructured once to create cap space, and Bailey was on the sort of long-term deal that only Jerry Jones & Co. hand out. Dallas gave its kicker a seven-year, $22.5 million deal before his fourth season, remarkable in a league in which only two other kickers (Mason Crosby and Ryan Succop) are on five-year pacts. The deal looked great when Bailey was healthy and kicking at a high level, but the Cowboys paid $7.3 million over the past two seasons for declining play before cutting him and eating the $800,000 in dead money.

Bailey's deal was low stakes, but the Cowboys structure their contracts to go longer than anybody else in the league by a significant margin. The NFL has established a precedent of handing out extensions of six years or more to quarterbacks and pass-rushers, in part because their deals are so expensive. Just 11 players who don't suit up in one of those roles across the NFL were signed to extensions of six years or more. Four of those players -- Travis Frederick, Sean Lee, Zack Martin and Tyron Smith -- are on the Dallas roster. (Bailey was the fifth.) Of the 19 players under contract for the 2023 season, three are Cowboys.

Those four veterans are the most notable veteran Cowboys after Jason Witten retired this offseason to become a color commentator on Monday Night Football. Dallas has repeatedly restructured each of these deals outside of the Martin contract, which only came into existence this June. They probably plan to turn most of Martin's $10 million base salary in 2019 into a signing bonus. (Dallas was doing this with Witten's contract as recently as this past March, but the most recent restructure was made in such a way as to protect the organization from Witten's retirement without incurring dead money.)

Again, this strategy is great as long as the players stay healthy and productive. Asking any NFL player to stay healthy and productive for eight years is betting against history and randomness. Take Lee, who has the third-highest 2018 cap hit in the league among coverage linebackers at $11 million after restructuring his deal in 2014, 2016 and 2017. He is wildly productive when healthy, but he has missed an average of nearly six games per year during the first five years of his extension. The Cowboys have had no way to get out of his deal without paying a minimum of $9.8 million in dead money. They probably drafted Leighton Vander Esch to serve as a long-term replacement for Lee, and if Dallas does decide to move on after this season, it will owe $3.1 million in dead money.

Smith's eight-year, $97.6 million contract is excellent, in part because the left tackle market has exploded since he signed it and because Smith signed it after his third year in the league. At the same time, though, he also missed time because of various injuries last season. Perhaps owing to that, the Cowboys stopped restructuring Smith's deal after doing so in each of the previous three seasons, pushing $27.7 million into the future. While Smith should still be an excellent player, he's not a bargain in 2018. The Cowboys are responsible for a $17.6 million cap charge with Smith this year, making him the highest-paid left tackle in the league. (His cap charges go down in future years as some of those restructures begin to come off of the books.)

In the case of something unforeseen, as is the case with Frederick, the cap problems can become far more painful. Dallas' star center is fighting Guillain-Barré syndrome, an autoimmune disease, with no timetable for a return. The Cowboys already have restructured Frederick's deal in each of his first two seasons; if Frederick is forced to retire or his play diminishes to the point in which they want to move on, they would owe $16.4 million in dead money next year or $11.4 million in 2019.

We all hope that Frederick returns at his prior level of play, and there's no way that Dallas could have expected Frederick to suffer from a rare illness, but signing NFL players to deals with extra years for restructuring purposes ignores the attrition rate and randomness of the league. The Saints had to deal with this when they gave Junior Galette an irresponsible four-year, $41.5 million extension, restructured his deal, and then were forced to cut him for off-field concerns. They ended up eating more than $17.5 million in dead money over two seasons.

It's not just off-field problems. Hall of Famers like Calvin Johnson have retired earlier than expected, with the Lions paying $12.9 million in dead money for his deal in 2016. Young stars like Tyrann Mathieu haven't developed the way their teams would have hoped, which is why the Cardinals are paying $9.3 million in dead money this year. Teams even grow sick of key contributors like Ndamukong Suh, whose $9.1 million dead money hit this season makes him the seventh-highest-paid player on the Dolphins, even as he suits up for the Rams.

Handing out these sorts of contracts also creates the possibility of a situation in which a player's combined salary and cap accounting becomes too much to handle. That's what happened with DeMarcus Ware in 2014, when the Cowboys needed cap space and were set to pay a 32-year-old Ware a $12.3 million base salary. Dallas already had restructured Ware's deal in each of the three previous seasons to free up room, but in 2013, Ware missed a game for the first time in his career and saw his sack total fall to a career-low six.

In lieu of a $16 million cap charge for Ware, the Cowboys cut their star edge rusher and ate $8.6 million in dead money on their 2014 cap instead. Ware promptly went to the Broncos and posted a 10-sack season before winning the Super Bowl with a 3.5-sack, 12-knockdown postseason the following campaign. Dallas spent years searching for pass-rush help and whiffed on players such as Hardy and Randy Gregory before DeMarcus Lawrence's breakout campaign.

What's next?

The Cowboys will find themselves at a crossroads in 2019. They're currently ticketed to have $64 million in cap space. They could have more if they decide to move on from veterans such as Lee and Tyrone Crawford, although they'll incur dead money charges after previously restructuring their deals. It's not difficult to piece together a scenario in which the Cowboys could end up with $80 million in cap space.

Unfortunately, a good chunk of that space isn't going to last long. Lawrence will be a free agent, and while the Cowboys could try to franchise him for another season at $20.6 million, the Boise State product doesn't want to play on the tag for a second consecutive year. If Lawrence comes close to his 15-sack total from a year ago, the Cowboys probably will have to pay him something close to $20 million per season on a long-term deal.

There's Prescott, who is in line for an enormous raise. Unless the third-year passer totally falls on his face in 2018, Dallas will almost certainly have to top the five-year, $137.5 million extension the 49ers gave Garoppolo as Jimmy GQ finished the fourth year of his rookie deal. The Cowboys will get a bit of a cap discount by virtue of signing Prescott in advance of the final year of his contract, allowing them to spread the bonus over an extra season, but he's not going to be on the books for the $815,849 he's currently posted at for 2019.

And, just in case you were wondering, there's no strong case to be made against giving Prescott a significant contract extension. Few rookie passers have been more impressive through two seasons. By the adjusted net yards per attempt index (ANY/A+), which accounts for era, he is off to the fourth-best start to a career since the merger, trailing only Dan Marino, Jeff Garcia and Russell Wilson. (Garcia, who spent most of his 20s in the CFL before taking over in San Francisco, isn't even a good comparison.) That metric doesn't even take into account Prescott's impact as a runner, which has seen him rack up 658 yards and 12 rushing touchdowns over the past two seasons.

The knock on Prescott is that he struggled without his star teammates around, which makes him just like, oh, every other quarterback in the league. Prescott has posted an 89.7 passer rating and a 69.9 Total QBR with Ezekiel Elliott on the field, and with Zeke sidelined, his passer rating has dropped all the way down to ... 86.6. Prescott's Total QBR of 70.3 actually improved without the star running back. As a comparison, over that same time frame, Ben Roethlisberger has posted a 95.8 passer rating and a 64.5 Total QBR with Le'Veon Bell on the field. When Bell isn't alongside him, Roethlisberger has mustered an 80.6 passer rating and a Total QBR of 52.8.

Likewise, when Prescott has gone without Smith at left tackle, his numbers have declined, but not by an extraordinary margin. With Smith, Prescott has posted a passer rating of 98.4 and a Total QBR of 76.0. Without the left tackle, those marks fall to 82.3 and 70.1, respectively. Compare that to Wentz, who spent most of his rookie season without the NFC's best right tackle, Lane Johnson. With Johnson, Wentz posted a passer rating of 99.1 and a Total QBR of 73.6. Without Johnson? Those numbers fall to 74.9 and 47.7.

Following Lawrence and Prescott off the board is Elliott, who will be eligible for an extension after completing his third season. The Cowboys could wait to sign their star back to a new deal, but as we saw with the Rams and Todd Gurley, teams are trying to get ahead of whatever Bell is going to get as a true unrestricted free agent next March. It wouldn't be shocking to see the Cowboys try to get an Elliott deal done in February in a deal that could top Gurley's four-year, $60 million extension.

The Cowboys can use these deals to make a change. While other teams restructure deals out of desperation (the Ravens) or foolishly aggressive spending (the Saints before 2017), no team manages its cap like Dallas. At this point, what evidence do we have that the Cowboys are gaining some sort of significant benefit from this plan? This is an organization that hasn't made it out of the divisional round in 23 years. It has been paying too much in dead money for players like Roy Williams and Jay Ratliff, let alone stars like Romo. Dallas simply hasn't run its cap in a responsible manner.

This is the Cowboys' chance to start running their cap like the rest of the league. They can't redo those offensive line contracts, but they should start structuring the deals they're going to give Elliott, Lawrence and Prescott in a traditional fashion. They are costing themselves opportunities by either being too naive to think their long-term contracts might not work out or by being too shortsighted to imagine what the future might hold. It already has cost them an opportunity every other team in the league is desperately trying to create. No team has done less with a star quarterback making peanuts than the Cowboys have with Dak Prescott.