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Teams who have great quarterbacks shouldn’t wait to pay them

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Dak Prescott and the Cowboys seem to be getting closer to a long-term extension, but the one major holdup left is the length of the contract.

The recent explosion in quarterback contracts has made one dynamic incredibly clear: The longer a team waits to pay a quarterback, the more expensive it will be.

That’s what the Cowboys currently are facing with Dak Prescott, a fourth-round pick in 2016 who has started 64 of 64 regular-season games and who now carries a franchise tender with a value of $31.4 million for 2020. The Cowboys want to pay him, they’ve tried to pay him, and the inability to get him paid has made the contract more and more and more expensive.

Whatever the team was willing to offer at the outset of the 2019 season, the price tag escalated as Prescott made it through another 16 games and, in turn, escaped his four-year rookie deal without injury. Now, the dynamics of the tag ($69 million for two seasons and then a potential Kirk Cousins-style shot at the open market) make it a lot easier for Prescott to request, and eventually to receive, $35 million or more per year.

It all could have been avoided, and teams that will be dealing with similar situations should use the Cowboys’ current conundrum as a cautionary tale for their own potential “good problem to have” -- a young quarterback who becomes eligible for a second contract.

The best approach, especially for a player who wasn’t selected in round one and who has only a four-year contract, would be to make the player an offer the day after the final game of his third regular season. That’s when, by rule, the window opens for a player to sign a second contract. (A surprising number of highly-compensated team employees and agents aren’t aware of this.)

If the Cowboys had approached Prescott after a Week 17 2018 win over the Giants and before the wild-card game against the Seahawks with, say, a five-year deal that would have paid Prescott $27.5 million per year (i.e., the Jimmy Garoppolo deal), maybe Prescott would have taken it. While the new-money analysis would have resulted in reports that Prescott actually signed a four-year extension with a new-money average value of $33.8 million, it would have been a five-year, $27.5 million contract from signing.

Fast forward 16 months, and Dak reportedly wants a deal worth more than $35 million per year from signing. That’s a $7.5 million bump, per year. That’s $37.5 million on a five-year deal. And that’s a direct result of the Cowboys not getting a deal done the moment the window opened on signing Prescott to a second contract but instead waiting and waiting and waiting and, consequently, watching it all get more and more expensive.

“As money gets bigger, deals get harder,” Cowboys executive Stephen Jones told #PFTPM on Friday. The Dak money got a lot bigger because the Cowboys didn’t do a deal when it would have been easier. And the longer they wait, the harder it’s going to get.