Here's what a Dak Prescott extension could look like, along with other Cowboys stars

Less than three weeks ago, with the Dallas Cowboys coming off a pair of solid road wins over the Philadelphia Eagles and Atlanta Falcons, team owner Jerry Jones put a price tag on how he valued quarterback Dak Prescott. Not only was Jones promising to sign him to a long-term extension, he boasted he wouldn’t trade him for two first-round picks.

“He’s our future,” Jones said.

That was before the past two weeks, which saw Dallas seize control of the NFC East and beat the NFL’s best team, the New Orleans Saints, in a signature 2018 win. If Jones loved Prescott when the Cowboys were just trying to climb out of mediocrity, how much does he love him now, with the team finally rolling again and looking to hit its full stride in the next month? More to the point, what must Jones pay in that promised extension?

In an effort to get a handle on that Prescott extension, Yahoo Sports polled a handful of opposing team executives and agents with experience negotiating quarterback deals. For added value, the sources were also asked to project the future of three other big Dallas deals on the horizon, including the immediate priorities of defensive end DeMarcus Lawrence and wideout Amari Cooper, and the further-out priority of running back Ezekiel Elliott. The responses were varied, but the overall notion was not. Essentially, Dallas is looking at a monster payout, potentially adding as much as $65 million or more in annual salary this offseason via extensions for Prescott, Lawrence and Cooper. A number that will bloat with an Elliott extension that isn’t expected by anyone to hit the books until 2020 at the earliest (and maybe as late as 2021). Factoring in that deal, it’s possible Dallas could be paying the foursome of Prescott, Elliott, Lawrence and Cooper as much as $80 million to $85 million combined per season as early as 2020.

Maybe the only surprise in the assessments? Prescott’s salary balloon (think: $25 million per season … or considerably more). With that in mind, here was the brass-tacks thought process on each player’s negotiation.

Dak Prescott

There will be a thousand ways to slice up this one, but everyone agrees on one thing: Prescott hired CAA last offseason to make certain he’s going to land near the top of the NFL’s quarterback heap when he signs his extension. CAA has previously signed record-setting quarterback deals with the Falcons’ Matt Ryan, Detroit Lions’ Matthew Stafford, New York Giants’ Eli Manning and Los Angeles Chargers’ Philip Rivers. Prescott signed with CAA because of this history of QB deals. That signals what he’s going to be pushing for in this extension.

We’ll see if Prescott can live up to that worth. But there’s a lot of debate about what the measuring stick is for him. Looking for NFL quarterback comparisons, his numbers and win percentages heading to the end of his third year as a starter compare favorably to the recent years of Washington Redskins quarterback Alex Smith, who is also represented by CAA. Smith’s numbers are key, having been established last offseason, when he signed a four-year $94 million extension. The deal included $55 million guaranteed at signing and an annual average salary of $23.5 million. Smith’s deal also had $71 million in total guarantees, including those for injury – a wrinkle that became relevant last month when Smith suffered a potential career-ending broken leg.

Interestingly, a handful of agents and team executives believe the Smith contract will likely be seen as far too cheap by CAA when it comes to “new money” figures. Particularly if Prescott continues the upward trend that began with the trade for Cooper five games ago.

“That [Smith contract] is conservative, honestly,” one AFC executive said. “Especially with the agents knowing that your owner said he wouldn’t trade the quarterback for two [first-round picks], the age of [Dak] and the salary-cap growth driving numbers.”

Considering the cap’s growth and Prescott likely signing his extension this offseason at the age of 25, the AFC executive pegged Prescott’s next deal as being more in line with “at least” $25 million to $26 million per year and maybe as high as $27 million per year in new money. That sounds crazy, but the thinking has a lot to do with Jones opening his mouth about Dak’s worth on the trade market. Jones essentially called Prescott a franchise player when he put the “two first-round picks” tag on him – and arguably considers him even more valuable than a franchise-tagged player, since he said that he wouldn’t take two firsts.

What this means at the bargaining table is that if Prescott is a franchise player and his current contract runs through 2019, the franchise tag estimations in 2020 and ’21 come into play. We don’t know what those figures will be, but using past data, a conservative estimate for the 2020 franchise tag will be $26 million to $27 million. Considering all the money pumping into quarterback deals, let’s call it an even $27 million. That would mean tagging Prescott a second time in 2021 would cost Dallas $32.4 million. That’s roughly $60 million for two seasons in guaranteed money at signing as a simple baseline. The last quarterback deal CAA did where guarantees at signing fell at $60 million was Matthew Stafford, whose salary averages $27 million per season.

Before Cowboys fans flip out, it’s worth noting the “new” money would kick in after 2019. So for practical purposes, you could look at the guarantees and Dak’s 2019 salary – which will be around $2 million due to NFL performance adjustments – and essentially equate it to paying Prescott $60 million to $65 million from 2019-2021 … an average of $21 million to $22 million per season before jumping up over $27 million per season for the remainder of the deal.

That may seem like a lot of money for Prescott. But it’s the price of doing business when the team owner essentially called him a franchise player.

DeMarcus Lawrence

There are a few clear points with this negotiation after speaking with team personnel and agents shaping up the free-agent market. Another franchise tag in 2019 would make this situation ugly (we’ll get to that). Lawrence would be the No. 1 available free agent if he hit the open market next offseason. This is a negotiation where Dallas knows it’s holding few cards at the bargaining table. So let’s get into all those points.

First, the ugliness. Everyone knows the franchise tag is almost universally loathed by NFL players. It’s never despised more than when it gets used on someone who would represent the No. 1 player in free agency. In a situation like that, a team is essentially inhibiting a player from locking down what is almost always a record-setting contract. Particularly when that No. 1 free agent is from the “prime” position quartet of quarterback, left tackle, edge rusher and cornerback. With that in mind, Dallas can expect another tag on Lawrence to be considered extremely unpalatable by the defensive end and his agent, David Canter. Possibly even to the point of contention that caused the irreparable rift between Khalil Mack and the Oakland Raiders last offseason. So mark this down – Lawrence and his camp will expect Dallas to move swiftly and decisively to sign an elite-level extension as soon as the official negotiation window opens at the end of the regular season. If that doesn’t happen and this turns into another tag situation, it’s going to be bad.

Second, the market. Lawrence’s sacks have been down, but he’s also being asked to play a more disciplined role in the Cowboys’ defense this season. He may not match his career high 14½ sacks from 2018 and hasn’t been perfect this year, but offenses are also scheming against him as a dominant player. He’s also a balanced run defender and, as we saw prior to the game against the Saints, a significant emotional leader in the locker room. Is he as indispensable as Mack or the Los Angeles Rams’ Aaron Donald? No. But he’s near that level, particularly when he’s at the top of his game. And that’s why he’d be paid like a top-three pass rusher on the open market. Supply and demand dictate it.

Finally, leverage. The Cowboys don’t have a lot here. If they choose the choppy route, the next franchise tag is $20.5 million. And, again, I cannot stress enough that another tag will be contentious. If Dallas goes that route, next up is the astronomical quarterback tag in 2020, which will be $29.6 million. Regardless of what Dallas does, those tags are important because they set a baseline for long-term negotiation. Just from a bottom-line standpoint, those two tags are the combined starting point for guaranteed money at signing – $50.1 million. But don’t kid yourself. That’s a low figure. Khalil Mack got $60 million in guarantees at signing and an average annual salary of $23.5 million. Lawrence will likely come in below those figures in a long-term contract. But not by a great deal, considering the salary cap is going up. The feel? For a long-term deal, the annual salary will be in the range of $21 million with a guaranteed-at-signing sum in the neighborhood of $60 million. The total overall guarantees will likely top out between $80 million to $90 million.

Amari Cooper

Cooper’s situation is interesting. Largely because there is motivation for him to gamble if Dallas isn’t offering an elite-level wide receiver deal right out of the gate. Before the trade deadline, Cooper’s camp wasn’t going to push suitors for a contract extension. He’s due $13.9 million on his fifth-year option in 2019 and early this season hadn’t yet warranted the mega-deal that most assumed he’d eventually sign. But in five games, Cooper has already had a very encouraging impact on the Dallas offense and that might be enough to stimulate some aggressive movement by the two sides. If you project his first five games with the Cowboys, a 16-game season from Cooper would fall somewhere around 96 catches for 1,360 yards and nine touchdowns. For comparison, that’s close to peak Dez Bryant production (although a little leaner on the touchdown receptions).

What does that mean for Dallas? First, it means Cooper represents the No. 1 wideout the team has been searching for. I think the Cowboys are already buying this notion, particularly seeing how Cooper has impacted not only parts of the scheme, but some of the recent run of success by Prescott and opportunities for opposite wideout Michael Gallup.

Cooper is making an impression. Maybe even enough for Dallas to offer him the lucrative extension now, rather than waiting into the 2019 season. As it stands, the negotiating bottom line of the next two franchise tags would be $30.6 million guaranteed at signing. But like Lawrence, that’s a conservative number given how much Dallas likes Cooper and has already invested in him.

The ultimate question is, will Dallas offer Cooper something in the top-five wideout range? The basement of that group is Brandin Cooks, who signed a five-year, $81 million deal with the Rams that included over $49 million guaranteed. If Dallas is inclined to get into that range, it’s likely a Cooper contract extension happens sooner than later. If the Cowboys aren’t ready for that level of commitment, Cooper will likely go into the 2019 season and play into his fifth-year deal, with the price potentially rising as he gambles on himself and gains more leverage.

Zeke Elliott

With two years left on his rookie deal – 2019 and a fifth-year option in 2020 – nothing is happening with Elliott this offseason. It makes no sense for Dallas to do the deal now unless Elliott was incomprehensibly open to a cut-rate deal (which he isn’t). And, frankly, the Cowboys are going to need some time the next two years to figure out how all the pieces and big contracts fit together before signing Elliott. Not to mention some more runway to see if he can keep himself free of off-field issues while also staying healthy.

Don’t rule out Elliott being a franchise-tagged player in 2021, either. This one has a long way to go and a lot of variables that will impact it.

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