What Would It Look Like, and Should the Dallas Cowboys Do It?

The next man up who’s playing at a near-elite or elite level makes the most money. It would behoove the Dallas Cowboys to hurry up and get a Dak Prescott extension done early this time to avoid the embarrassment of costing themselves millions of dollars more than was necessary… again.

Jalen Hurts was the highest-paid player in league history from an average annual value perspective. But that didn’t last long because the Baltimore Ravens finally came to terms with Lamar Jackson, who now holds the title for the highest-paid player annually while earning the largest signing bonus ever at $70 million. If the timing of each deal had been different, those values may have swapped. That’s how QB contracts work.

It’s time the Cowboys got ahead of the game.

Extend Dak Prescott With Expediency

The early bird gets the worm. There are a few adages that ring truer when it comes to dolling out contracts for quarterbacks. With extensions for Justin Herbert and Joe Burrow looming, Dallas would be smart to get a deal inked with Prescott immediately. Because in the end, the money will appear outrageous to start but almost instantly fall into where the player is likely valued among the league’s best.

At one point, Prescott earned the highest-paid signing bonus for a QB ($66 million) until Jackson’s recent new deal. His $40 million average ranked behind only Patrick Mahomes at the time. Now, that average is tied for the ninth-most money annually, a tie he shares with division rival Daniel Jones and Matthew Stafford. Three quarterbacks average over $50 million now. Russell Wilson sits at $49 million.

Prescott has never worried about these things, at least not publicly. And that makes sense, because Prescott is represented by Todd France, who was formerly with CAA and now resides with Athletes First. He’s a ruthless negotiator, which is obviously good for the player and not-so-good for Cowboys fans who have to constantly deal with the Jones family needing to feel like they won the deal.

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The undercut is a popular tactic used in Formula 1. The idea is to pit before the opponent the driver is following. The idea is to get a fresh set of tires that allow the driver to set a new blistering lap time, while also likely forcing the opponent left on the track to pit immediately after. Those new tires can often be quick enough to make up the difference that was left between the cars on the track, giving the car who pitted first a slight lead by the time the next car returns to the track.

That is essentially what NFL teams should try to do every… single… time… a QB is extension eligible, and the two sides know they want to continue their marriage. And while getting a tattoo of your significant other is usually bad luck, it feels a bit different in this instance. Prescott grew up a Cowboys fan, and his loyalty to the city is not just a surface-level facade. He wants to be a Cowboy.

“I’m excited to be a Dallas Cowboy,” Prescott said at the Grant Halliburton Foundation’s Beacon of Hope luncheon about mental health awareness in March. “Always dreamed to be here. Now that I’m here, I don’t expect to play for any other team. Now it’s just about winning and now it’s about to get that done and just to hear the [support from the] front office. Looking forward to an extension. When that time comes, it will happen. I’m with Stephen (Jones), it may just happen overnight. When it happens, it happens. It will be great.”

And suppose Jerry Jones was being honest about his assessment of Prescott when he said he views his ability to continue to make a greater individual impact on the team like Tom Brady did as his career advanced. In that case, there should be nothing stopping him from getting something done with France.

“I don’t want to dare do this to Dak or me or anybody, but I think just as (Tom) Brady became, in my mind, better and better and more impactful on how [his team] won as he got into his career, I think Dak really has those qualities,” Jones said on his famous NFL Combine bus.

What a Dak Prescott Extension Could Look Like

As K.D. Drummond wrote for The Cowboys Wire in late March, we need to make a few things clear. No matter what disgruntled Cowboys fans want, Prescott’s baseline is over $50 million annually. Considering Hurts’ shorter body of work and Jackson’s play style and injuries are concerning, Prescott will likely command more than Jackson, even if he hasn’t been a pillar of good health himself over the past few seasons. The truth is, Prescott’s style is less concerning, and that matters in negotiations.

Jackson’s deal almost surely puts Dallas behind the eight ball in negotiations. He received a $72.5 million signing bonus, $112.5 million guaranteed at signing, and $185 million in total guarantees. That total guaranteed number is $20 million more than Wilson, and his $135 million in fully guaranteed money is second only to Deshaun Watson, whose contract is absolutely absurd.

France will undoubtedly fight for a three-year extension to try and allow Prescott to hit the market again as early as possible, which makes sense considering the league’s salary cap is expected to absolutely skyrocket over the next few seasons. The Cowboys will undoubtedly want it to be a five-year extension. They may as well meet in the middle now.

Projected Contract Extension: Four years, $210 million

  • $75 million signing bonus
  • $52.5 AAV
  • $185 million total guarantees
  • $140 fully guaranteed
  • No trade/tag clauses
  • Two void years to spread the signing bonus out

While Prescott might not be able to secure what Burrow receives in his eventual deal, Burrow’s deal would act as a gravitational pull for France, as the money they expect would inch closer to the top of the market.

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If the Cowboys truly want Prescott to play his entire career in Dallas, they should swallow a bit of their pride along with some Johnny Walker Blue Label and make a few concessions to France and get this deal done sooner rather than later.

Because this deal is already more expensive than the one Drummond projected less than two months ago.

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