Stephen Jones credits Dak Prescott for a gutsy negotiating strategy. He has to say that about the Dallas Cowboys quarterback, who is about to begin his fifth NFL season. Otherwise, the team’s chief operating officer and his father, Cowboys owner Jerry Jones, would have to admit mishandling the contract process.

Over the past year, Prescott and his agent may have played the Cowboys better than Yo-Yo Ma ever played the cello.

The Dallas Cowboys will regret not getting a deal done

By most measures, the Dallas Cowboys accomplished plenty during the offseason, beginning with completing their coaching change. It became apparent late in the 2019 NFL season that Jerry Jones did not intend to bring Jason Garrett back, and he moved quickly in January to hire former Green Bay Packers coach Mike McCarthy.

Jones also locked down Amari Cooper in March before the wide receiver acquired midway through the 2018 season could field offers in free agency while coming off a 79-catch year with eight touchdowns.

The Cowboys landed two of the key targets later in March by signing Carolina Panthers defensive tackles Gerald McCoy and Dontari Poe, giving McCarthy one less position group to worry about when the ensuing COVID-19 pandemic disrupted offseason preparations.

Jones drafted promising receiver CeeDee Lamb in the first round and cornerback Byron Jones in the second. And, perhaps most importantly, he signed former Cincinnati Bengals quarterback Andy Dalton. Jones delivered a message that the Cowboys expect to win and will not be derailed by an injury to Dak Prescott.

What Jones and the Cowboys did not get done, however, was a new contract for Dak Prescott. Talks between the team and the quarterback dragged on forever. Prescott wanted more money over a shorter contract than the Cowboys were willing to offer.

While the Kansas City Chiefs and Houston Texans worked methodically to sign Patrick Mahomes and Deshaun Watson, respectively, to lucrative extensions, Prescott forced the Cowboys into applying the franchise tag.

That could set Prescott up for free agency in 2021.

Jerry Jones is preparing to pay Dak Prescott a lot of money

The $31.4 million that Dak Prescott earns this season will be a nice bump from the $4.9 million over four years in his rookie contract. But it leaves him far short of what Patrick Mahomes and Deshaun Watson secured this summer.

Jerry Jones and the Dallas Cowboys are preparing for the inevitable: They will have to pay a premium to Dak Prescott if he leads a deep playoff run and likely even pay for a 9-7 year and a one-and-done postseason — unless they can brew a magic potion that lands the Cowboys Trevor Lawrence in next spring’s draft.

The Cowboys have been clearing cap space. Offensive linemen Zack Martin and Tyron Smith previously restructured contracts, and ESPN reported that defensive end DeMarcus Lawrence recently agreed to convert most of his salary to a signing bonus to free up $12 million more.

The moves don’t affect Prescott directly since the sides can’t deal again until the 2021 NFL business year begins in March. However, the Cowboys can use the extra space to lock in other veterans in anticipation of the 2021 salary cap plunging due to the pandemic’s effect on revenues. Then, the Cowboys can restructure deals again to free up what they’ll need to satisfy Prescott or to simply apply the franchise tag again, this time at about $37.7 million.

“It’s so difficult for us,” Cowboys COO Stephen Jones told Dallas radio station KRLD-FM. “As you know, we’ve never not gotten a player signed that we wanted to get signed, but this one’s been a little more difficult. We’re talking about a situation where he’s going to represent so much of your salary cap.”

Stephen Jones respects that Dak Prescott ‘bet on himself’

By rejecting all the Dallas Cowboys’ proposals and accepting the franchise tag, Dak Prescott risks missing out on huge future earnings if he performs poorly or is seriously injured. On the other hand, he’ll have the $31.4 million from this year. Plus, he’ll enter new negotiations with Patrick Mahomes and Deshaun Watson having already set the pay standard for quarterbacks.

And, who knows what sort of megadeals others might sign before next March. Despite the impending brief reduction in the salary cap, Prescott stands to reap more money than he could have signed for this spring or summer. That’s especially true if the upcoming new NFL television contracts generate the expected windfall for teams.

“I admire him because he never blinks,” Stephen Jones told the radio station. “I’d have said, ‘Run in there and take that big guarantee and sign up.’ But I do think he’s made money playing it out. We’ll see what happens with the cap and how the virus affects our revenues for the upcoming couple of years. But … he’s bet on himself and bet wisely. He’s answered every bell, every call.”