After contract win, Cowboys' Dak Prescott could earn more money than any player in NFL history

For two years, Dak Prescott gambled on himself. And for two years, the Dallas Cowboys sat across the table and bet against their starting quarterback and the mushrooming pay scale that surrounded him.

On Monday, the impasse was broken. Or if we’re searching for a more accurate descriptor, Prescott smashed it.

The 27-year-old QB achieved a four-year, $160 million deal that essentially makes him the highest paid player in NFL history (based on his contract value at signing) and sets Prescott in the running to achieve a gargantuan windfall over the course of his career that could ultimately make him the richest player the league has ever seen. That’s what Monday’s deal ultimately means for Prescott, who reached a $40-million-per-season plateau shared by Kansas City Chiefs quarterback Patrick Mahomes and Houston Texans quarterback Deshaun Watson.

What sets Prescott apart from those players is his next window into extension negotiations, which should in theory take place after the third year of this deal (following the 2023 season). That period is considered significant because it will take place in the midst of a massive financial windfall of NFL revenues that will include a new television deal and what is expected to be expansive earnings related to gambling revenues skyrocketing over the next decade.

Any way you calculate it, it’s a landslide of a win for Prescott and his camp, which has been angling for an upper-level quarterback deal for the past two years, with their leverage exponentially increasing with each passing offseason. Now it has led Prescott to a remarkably lucrative intersection of spiking increases on the league’s quarterback pay scale and a robust financial future for the NFL that will drive free agent prices even higher in the the next decade. And it all comes in the time frame when Prescott and his camp desired: Inside a four-year deal rather than the five or six years of control that Dallas initially desired.

Dallas Cowboys' Dak Prescott (4) and Tony Romo (9) talk on the sideline in the first half of an NFL football game against the Baltimore Ravens on Sunday, Nov. 20, 2016, in Arlington, Texas. (AP Photo/Michael Ainsworth)
Dak Prescott has come a long way since he was a fourth-round draft selection and Tony Romo's backup. (AP Photo/Michael Ainsworth)

Prescott is on pace to sign as many as two more extensions inside this decade, given his chosen frame of four years of control. If that wasn’t enough, Prescott also has a powerful no-trade clause in this deal, along with Dallas having to franchise Prescott this week while it works out the details of this extension (which will count as Prescott’s second tag and virtually guarantee he can never be tagged again by any team in the future)

When you parse all of that out, Prescott won the money, control, freedom and years that he was looking for. Maybe the only thing he didn’t get was the ownership rights to the “D” in Dallas.

Here's what Jerry Jones, Cowboys got at bargaining table

The deal isn’t an entirely lost proposition for the Cowboys, either. Not only does the franchise have its core leader locked up for the next four seasons, Prescott’s four-year extension is actually a six-year deal that voids down to four. That’s a vital reality for Dallas because it means the team gets to technically spread out his signing bonus over a six-year span. It’s a mechanism to lessen Prescott’s cap hit in 2021, which the deal does by lowering his salary from a $37.7 million franchise tag figure down to $22.2 million. That’s a significant change for the Cowboys, who will be looking to create breathing space when the salary cap is ultimately rolled back after the 2020 revenue shortfall from the pandemic impact.

And if we’re looking at this as a glass-half-full scenario for Dallas, it’s also worth mentioning that Prescott’s deal comes on the heels of his 2020 franchise tag. Technically, it means that Dallas ultimately achieved the five years of control that it was attempting to gain in negotiations last offseason — with one year coming under the 2020 franchise tag and then four years coming via an extension. If you look at this deal from that angle, it means Dallas has gotten the five years of control it sought last year (from 2020-2024) for somewhere between $191 million to $194 million depending on incentives. Is that significantly more than Dallas would have paid if it had done a long-term deal before the 2019 or 2020 season? Yes. But team owner Jerry Jones can ultimately point to Prescott having a five-year payout of around $38 million and frame that number as nothing more than another market-pacing deal rather than a blowout loss at the negotiating table.

Most contract negotiators will tell you it’s a sure sign of defeat if you have to work that hard to find the proper framing for your deal. But if it makes Jones and his son Stephen sleep better at night, so be it. History will remember that Dallas could have had Prescott for far cheaper and a far more lengthy deal if it had worked to get ahead of the quarterback contract curve following the 2018 season, Prescott’s third year as a starter. It didn’t, perhaps believing that Prescott’s market would ultimately settle far lower than it ultimately did.

How talks between Prescott, Cowboys heated up

The result was a negotiation that dragged on through some contentious lows, all while other market-setting quarterback deals were being cemented. And while the two sides got within shouting distance of each other last offseason, it wasn’t until last week that talks again became more productive between Stephen Jones and Prescott’s agent, Todd France. Ultimately, Jones blinked, giving in to the four-year, $160 million threshold for the tradeoff of a structure that would lower the immediate salary hit. And while Jerry Jones has appeared to have taken a backseat in these talks, it’s worth considering that the 78-year-old franchise owner was strongly reticent to start over again at a quarterback spot that can spiral into a search lasting years if not decades.

That sure helped penetrate the impasse that lingered between the Cowboys and Prescott’s camp, although it didn’t pick up steam until last week. Indeed, the situation was uncertain enough coming out of the weekend that one source familiar with the talks suggested that a likely scenario was Prescott getting tagged Tuesday and then the two sides ironing out a five-year, $200-million deal by July. The potential complication with that approach is that Dallas would also be in an even weaker position, with Prescott virtually certain to be heading into free agency following 2021 and putting its fate into the hands of other teams that would very likely bid his price even higher than what it is now.

Ultimately, Dallas came to its senses and declined to let other teams set the table with Prescott. And the result was the Cowboys absorbing a loss at the negotiating table that was two years in the making. Maybe it was because Dallas had to get Prescott’s cap number lower in 2021 to keep from backing the team into a difficult corner with its roster. Or perhaps it’s because Jerry Jones knows that the next television deal and wave of gambling revenues will cover it (and maybe because of both).

The resulting outcome was Prescott reaching astonishing salary heights for a player who was a fourth-round pick in 2016 and setting himself up for potential history if the next four seasons play out as he hopes.

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