Art of the Deal: How Todd France Secured Dak Prescott the Greatest Contracts in NFL History
Cowboys Dak Prescott has a career earnings of $247,687,392, tenth most of all-time for any NFL player.
The Dallas Cowboys and quarterback Dak Prescott have met at the negotiating table more times than most NFL players will ever see in their careers. Prescott has signed three deals during his time with the Cowboys. His first one as a rookie, his second before the 2021 season, and the third last year to become the highest-paid player in NFL history.
No negotiation is ever the same. On the surface, the discussions with Prescott’s team and the Cowboys have sometimes been lengthy and complex. When deals materialize in sports, it often takes time for stories to surface about what transpired among the front office, the player, and their representatives. For the first time, we hear the agent’s perspective regarding the contract negotiations between the Cowboys and Athletes First, the agency representing Prescott.
On episode ten of the Athletes First Family Podcast, CEO Brian Murphy, VP of Client Strategy AJ Stevens, and Prescott’s agent Todd France talk about the timeline of every negotiation, how they continued to bet on each other, and what finally led to the record-setting deal in 2024.
*I do not own the rights to any of the clips you see. They are being used for content purposes only.*
Betting on themselves in 2019 and 2020
At the beginning of the 2019 season, Prescott was entering the final year of his rookie contract with the Cowboys. At that time, the third-year quarterback was coming off his second playoff run and first postseason victory. He had two Pro Bowls on his resume and was named 2016 Rookie of the Year.
The timing made sense for Jerry and Stephen Jones to consider the team's long-term future and potential commitment to Prescott with the negotiation window open after completing the third season of his rookie deal. The front office and Athletes First discussed a contract extension around training camp, and the Jones Family was willing to offer Prescott a five-year deal with $100 million guaranteed.
It is a considerable amount of money for a player drafted in the fourth round who will only make just over $2 million in his final year.
However, France was thinking long-term, considering Prescott’s trajectory as an NFL quarterback, the market at the position, and being the face of America’s Team. He knew a four-year deal was necessary for his client and his future. It would ensure Prescott had another bite at the apple to make substantial earnings in his prime.
Todd France : “It’s not what we wanted. I mean, you obviously want to get a deal done, but you want to get THE right deal done, not any deal done. While you are walking away from $100 [million], you could also look at it by that the extra year, you’re also walking away from $100 [million] or giving up $200 [million].” (12:49)
When a deal couldn’t be reached, Prescott entered Week 1 with the understanding he would be an unrestricted free agent at the start of the new league year in 2020.
Prescott played well in 2019 despite Dallas not making the playoffs and going 8-8. He threw for a then career-high 30 touchdowns and was just 98 yards shy of a 5,000-yard passing season. The franchise decided to course correct. Jason Garrett was no longer the head coach; the team hired Mike McCarthy, and he was excited to work with Prescott as his quarterback.
The Cowboys' front office is well-acquainted with using the franchise tag to retain a player’s rights and extend the negotiating window for a new deal. In 2018 and 2019, they used it to keep DeMarcus Lawrence in Dallas before agreeing to a contract extension. In 2020, they applied it to their quarterback before he hit free agency, hoping to iron out a contract. Prescott would be guaranteed to make over $31 million on the tag for the season, regardless of a new deal.
During the 2020 negotiation period, AJ Stevens started working at Athletes First and tried to help France work out a deal between Prescott and the Cowboys before the franchise tag deadline in July. Again, the sticking point in the conversations came down to the number of years on the contract, with Dallas wanting five and Prescott’s camp wanting four.
AJ Stevens: “As we explained in previous episodes, the four-year term is of the utmost importance to us and quarterbacks because of the way that the market grows and the salary cap grows and the desire to get back to the market for these guys and maximize their career earnings...the offer was up across the board in all aspects, except for it was still a five-year deal.” (14:57)
The Cowboys front office and France could not agree on a deal before the deadline to sign the franchise tag approached, and Prescott would play the 2020 season on the tag. Walking away from the $100 million guaranteed was an easier pill for the star quarterback to swallow, considering the money that would be coming his way.
AJ Stevens: “It’s a little bit different of a decision because Dak's final year of his rookie contract: $2 million. So it’s $2 [million] or $100 [million], and then it’s $31 [million] or $100 [million]. Then I remember one of the conversations with Dak was, ‘I walked away from a hundred to play for two, now I’m gonna walk away from a hundred to play for for thirty-one, like this one actually is a little bit easier to decide on.’” (15:35)
France talked about how he, his team, and Prescott walked through every scenario with what was on the table and even risked losing money depending on how the 2020 season turned out. Prescott, like in 2019, chose to bet on himself.
Unfortunately, the worst possible scenario occurred. A few weeks into the season, Prescott sustained a severe ankle injury against the New York Giants. The injury caused him to miss the entire season and should have set plans for Prescott's near-top-of-the-market extension into flames.
What now? Prescott would be a free agent two years in a row, but this time, it was different—he would be recovering from a severe ankle injury with others on the outside questioning his NFL future.
Prescott’s first veteran contract in 2021
Despite the severity of Prescott’s injury, the disaster that was the 2020 season could have played a role in the Cowboys’ willingness to commit to him long-term. It showed the Joneses what life would be like without Prescott as their franchise quarterback.
Mike McCarthy was entering his second season as head coach and was brought to Dallas to put the team over the hump as Super Bowl contenders. It’s tough to do that without a capable quarterback.
At the beginning of 2021, the Cowboys’ front office felt comfortable enough with Prescott’s rehabilitation to resume contract discussions, ensuring their quarterback of the future would continue to wear No. 4.
Here is how those negotiations went.
As mentioned in the clip, Mike Florio of Pro Football Talk labeled the deal the best contract for an NFL player of all time. One-half is the money that went right into Prescott’s piggy bank at signing, along with the player-friendly leverage created by the deal. The other half (*and here is where the art of negotiation comes to life*) is how Prescott’s agents made the Cowboys front office pay for drawing out negotiations with their client to the last minute.
France and his team wanted not only a no-trade and no-tag clause in the contract but also made them use the tag on Prescott before the deadline passed, making sure he would forever be a player who was issued the franchise tag twice.
That means the new team's hands would be tied if Prescott ever signed as a free agent with another team and encountered contract disputes similar to Dallas. The new team would almost be forced into offering a contract extension or letting him walk, as a third use of the franchise tag on a single player would severely impact any team’s salary cap.
That's pretty brilliant thinking from France and Athletes First.
There is also another thread to the story behind this deal. Once France called Prescott to let him know the numbers had been agreed to, he told his client to hang tight because they were negotiating language in the deal that could have voided his guaranteed money if the NFL had fined him.
Well….
It’s a good thing Prescott trusted the advice of his agent. At the end of the Cowboys loss to the San Francisco 49ers in the Wild Card round of the playoffs, people were throwing things at referees as they walked off the field as their actions directly impacted the final play of the game.
Prescott then spoke at the podium, saying it was “sad” that fans would throw garbage at players walking off the field. Someone from the media corrected him that it was actually towards the referees, and he said, “Credit to them then. Credit to them.” The quarterback apologized right away, saying he “deeply regretted the comments,” but the NFL took action and issued a fine of $25,000 for his comments. That moment could have potentially voided his guaranteed money had France and his team not gone through the deal with a fine-toothed comb and changed the language of the deal.
At face value, the 2021 extension with Prescott averaged $40 million annually; however, as France mentions, it was a $42 million per year deal over the first three seasons. Since the Cowboys could not tag him after that fourth year, it would be wise for Dallas to discuss a new deal with Prescott and his camp after the 2023 season, potentially allowing him to earn more money a year early.
This is exactly how France wanted to play it—making sure this deal was just the opening act for the big headliner down the line, which would either come from the Cowboys or a bidding war for Prescot in free agency.
All roads lead to the highest-paid QB in NFL history
So if Prescott could get a near top-of-the-market deal coming off injury in 2021, what would his market be after the 2023 season, in which he finished second in MVP voting and had his best season as a pro? Prescott’s agency knew there was significant money to be made before the 2024 season—their plan all along.
This time, the rose-colored glasses were off. Prescott wasn’t a rookie negotiator anymore. He is well-acclimated to how the Cowboys do business with extensions. It usually takes time in Dallas and is never on the same timeline as when a player hopes to finish it.
Lucky for Prescott, the front office’s usual strategy was his financial gain. In the 2024 offseason, Trevor Lawrence, Tua Tagovailoa, and Jordan Love received new deals, resetting the market. Prescott could SURELY make more if quarterbacks of their tier made around $55 million annually. The Cowboys’ passer was better in almost every statistical category than the three quarterbacks mentioned.
The advantage of having one agency, Athletes First, represent several top-tier players is that during the negotiations between Love and Tagovailoa, Prescott was kept informed about the potential status of his market once those deals were finalized.
If Dallas had been proactive, it could have been the opposite. Maybe Athletes First would have visited other quarterback camps to discuss how the Prescott negotiations would affect their deals, but like always, the Cowboys prolonged the situation.
Todd France: “They [the front office] started very late when they came back to us. They could have done it all offseason. When Dak’s getting ready for camp and getting into camp, the switch flips. He does not want to be involved in or having conversations about the contract...he didn’t even want to be updated unless there was something worthy to be talked about. Now I still did and he still heard it, but they were shorter conversations. They weren’t near as in depth as the first go around because he was in training camp. That’s where he wanted to be and that’s where that’s mindset was. He [Prescott] was willing to bet on himself. He’s like, ‘That’s fine. If they don’t want to do a contract, I’ll be a free agent. Of course the Cowboys were banking on the Star on the helmet and that no matter what he’s gonna come back. It wasn’t gonna work out that way had a deal not worked out, I really believe that.” (38:03)
Being the Cowboys quarterback is unlike any position in the NFL. While it may attract a great deal of unwarranted criticism, it also opens numerous doors for marketing and partnership opportunities, allowing one to be the face of a brand and earn more off the field. The Jones’ use of this negotiation tactic is smart, but it cannot be the only card up their sleeve. It’s weathered, wrinkled, and has faded into more of a joker at this point than an ace.
If the front office hoped that would serve as the tipping point in their favor, it sounded like the entire Prescott contingent felt comfortable entering a likely bidding war with 31 other teams, with Dallas sitting on their hands, unable to prevent it from happening.
So, if Jerry and Stephen Jones want to wait, when is the last chance to make a deal?
For the most part, Prescott did not make any demands during this negotiation and let his team handle everything. However, he did want a firm deadline of Week 1, and no discussions of a new deal would occur after that.
AJ Stevens: “I guess this is the one thing Dak did come in on is either the deal was done, or he was stepping on the field for Week 1 of the season, and I’m playing the season out. I’m not gonna have this back and forth during the year. I don’t wanna be on the bye week thinking about my contract when I need to be thinking about what is the next team we’re gonna play. How are we going to keep this thing rolling and get to the Super Bowl…
…We get the last four or five days before the first game of the season and they’re [the team] in game prep. They’re getting ready for Week 1 against the Browns and we’re still to a point, I think it was Thursday, we get a proposal from the Cowboys and I go through it quickly and Todd just looks at me and just goes, ‘We’re not gonna get a contract done.’
We’re just gonna have to tell Dak play this out and we’re gonna be great in free agency. This is gonna be unheard of, like this gonna be a lot of fun probably when we get to free agency, but it’s also on the otherside of it you’re sitting there saying it’s $160 or $180 million of guarenteed money that was on the table at the time. We’re still sitting there still saying it’s not enough, it’s not what it needs to be, it’s not what Dak deserves given everything he’s had to do and everything that we’re forcasting in the market.” (41:00)
Maybe the Cowboys thought if they waited long enough until Prescott’s imposed deadline struck 11:59, he would accept whatever deal was on the table to move forward because he might not wanted the distraction hanging over the team all season. But France and his team knew they had the Cowboys over a barrel. It’s like they hand-crafted a white flag for them and presented it to the front office, knowing eventually they would have to wave it.
The market for Prescott would have been out of this world in the hypothetical scenario he reached free agency this offseason:
He is a player in his prime for his position at 31 years of age
Two seasons removed from an MVP-level performance in 2023
An outstanding player for the locker room and community as a Walter Payton Man of the Year winner.
His accolades would have been enough alone to spark a bidding war, but add that to the free agent quarterbacks available this cycle (Sam Darnold, Aaron Rodgers, Russell Wilson) and the lackluster draft class (Cam Ward and Shedeur Sanders), Prescott could have made way more than $60 million a year. The Cowboys could not afford to compete in an open market for their quarterback.
“That was the theme of a lot of the conversations,” France said. “Like whatever we take is a discount.”
France talked about how, yes, one goal of Prescott’s was to remain a member of the Cowboys organization, but if the front office was not going “to participate in a fair business proposal,” then Prescott understood the reality of him not being in Dallas if it came to that.
Thankfully, no one has to live in that reality, and Cowboys fans were saved from the absurd amount of content that would have been on sports networks this offseason discussing that narrative.
Hours before kickoff, Prescott and Dallas agreed to a four-year, $240 million contract extension with $231 guaranteed and an average of $60 million a year, surpassing everyone else in NFL history as the highest-paid player.
France talked about how his initial FaceTime with Prescott was of few words and that both men were overcome with emotion and relief that this was finally behind them and a deal was made.
I don’t know if anyone has let the higher-ups in the organization know, but contracts don’t have to be done this way. It is possible to have a proactive approach and get things done early so there is no market resetting, and the team can be players in free agency.
Stephen Jones spoke to the media at the NFL’s league meetings this week and said they put “zero credibility or credence into people saying we wait too long” to get deals done with their players. Well, the truth is they do. If Prescott imposed a hard deadline of Week 1, getting an agreement ironed out minutes before the player leaves the hotel to get on the bus to the stadium is considered, in most parts of the world, waiting too long.
What did we learn?
Who knows if France and Athletes First would have accepted offers from the Cowboys earlier in the negotiation process for all deals, even at a lower price, as long as they agreed to the four years they wanted.
At the end of every episode of the Athletes First Family Podcast, CEO Brian Murphy asks, “What did we learn?” I would answer that question by saying Todd France is one of the more hardened and creative negotiators in Sports Business, and you can see why he’s negotiated top-of-the-market deals for almost every position in football.
The second lesson learned is that the Cowboys need to examine their negotiating style and see if it’s costing them in the long run. They need to decide whether to pay Micah Parsons, DaRon Bland, Tyler Smith, Brandon Aubrey, and Jake Ferguson as the franchise's next cornerstone players.
At least two of them could command top-of-the-market deals at their position (Smith and Aubrey), and Parsons will no doubt become the highest non-quarterback player in NFL history. “Deadlines create deals” should be a line in Dallas that takes on the first word of its phrase—be dead and buried.
(To watch Episode 10 of The Athletes First Family Podcast, click here.)