On Monday, Cowboys EVP Stephen Jones insisted on ESPN Radio 103.3 in Dallas that the deal must be "team friendly."
"At the same time, and I know Dak wants this, you want a supporting cast," Jones said, via the Dallas Morning News. "That's the way to go down as being one of the great quarterbacks to ever play the game: win championships.
"There's been a lot of good players who won a lot of games and have good stats, but if you don't have championships, certainly there's an empty feeling there. I know Dak. His No. 1 goal here is to win Super Bowl championships. He's a winner; he's a leader.
"I just feel good that we'll find our way to a place that the contract enables us to surround him with a great supporting cast which a lot of it's in place. If you look at our offensive line, look at our receiving core, you look at Zeke: a lot of it's there. Obviously with [Jason] Witten coming back and some young tight ends, certainly that's a nice spot for us, too. So we've just gotta keep building on that and be able to fit Dak in.
"He certainly deserves to be paid fairly. He's a fourth-round pick out of Mississippi State, as we all know. He's never made a lot of money, per se, with his contract. Certainly deserves to be paid and be paid fairly."
Jones' dueling phrases causes some convolution. "Team friendly" and "paid fairly" don't necessarily sing harmoniously together.
Jones noted that the team has yet to begin deep contract talks with the QB, so sides being far apart at this stage isn't a surprise.
As a fourth-round pick, Prescott has made peanuts compared to his worth. For his first three seasons, Dak's base salary has been below $650,000 -- a figure some mid-level free agents get as a signing bonus. This year his salary finally jumps over $2 million, but even that is pennies on the dollar for a starting quarterback. Forty-one QBs have a salary cap value higher than Prescott's in 2019, per Over The Cap. 41. That list includes such luminaries as Brian Hoyer, Chad Henne, and Nate Sudfeld (the Eagles' backup's backup last season).
"Deserved" could be in the eyes of a beholder for a QB that has helped the Cowboys to two division titles in three seasons, but still seems to have major doubters within the fan base.
If sides can't come to an agreement on Prescott's worth, the franchise tag dance seems destined to follow this offseason and perhaps next. Kirk Cousins showed the way to free agency if Prescott wants to get there badly enough, or if the Cowboys insist he take less than top dollar so they can spend elsewhere.
With multiple young players in line to get paid, money management could get tricky in the next couple years for the Joneses.