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Dallas Cowboys quarterback Dak Prescott switched representation to the famed Todd France of CAA Sports two years ago.

This move was made with the 2020 offseason clearly on Prescott’s mind. A mid-round pick from Mississippi State, Prescott was coming off a dazzling first two years in the NFL and was already looking for that big pay day.

The big picture: Now that Prescott is about a month away from becoming a first-time free agent, his relationship with France adds another layer to what has been a drawn-out negotiating process.

We’ve seen this a lot in the past; top-end impending free agents switching representation.

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In going with a respected agent in France, who is known for being a tough negotiator, Prescott made it clear to the Cowboys that he’s going to play hard ball. The foundation was laid. The writing is now on the wall.

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Prescott and Cowboys remain at an impasse: This has been one of the craziest extension negotiations in recent history.

• Initial reports indicated that Prescott was looking for $40 million annually. Those reports have been pushed back against since, likely coming from Prescott’s side.
• In turn, the Cowboys reportedly offered a deal that would have made Prescott a top-five paid quarterback with $90 million in total guarantees.
• The average of the top-five quarterbacks is about $33.7 million per season. That fits in with the $34 million Prescott was reportedly offered by the Cowboys ahead of last season.
• The $90 million in total guarantees would rank outside of the top-seven among quarterbacks in the NFL. Hence, the divide.

Things are changing: Since Dallas’ reported offer of $34 million annually, other quarterbacks have reset the market. The dynamics have changed.

• Russell Wilson: Four-year, $140 million deal with $107 million in guarantees.
• Jared Goff: Four-year, $134 million deal with $110 million in guarantees.
• Carson Wentz: Four-year, $128 million deal with $108 million in guarantees.

As you can see, France is negotiating from a position of power here. The longer Dallas waits on a long-term deal, the more the market increases. Even when we eliminate Wilson from the conversation, the deals Goff and Wentz inked shifted the market in Prescott's favor big-time.

The agent: France is among the most successful reps in the industry, continuing to reset the market for his clients.

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• Aaron Donald: This two-time NFL Defensive Player of the Year inked a record-breaking six-year, $135.5 million deal with the Rams after a holdout back in 2018. He’s the highest-paid defensive tackle in the game at $22.5 million annually with $86.9 million guaranteed.
• Fletcher Cox: Much like Donald, Cox took advantage of the market. Signed back in 2016, the Pro Bowler set the market with $17.1 million annually.
• DeAndre Hopkins: Despite inking his deal back in 2017, Hopkins is the sixth highest-paid receiver in terms of average annual salary ($16.2 million). He reset a market that has since been surpassed five times.
• Joey Bosa: His now-infamous holdout as a rookie back in 2016 changed the dynamics big-time. The current CBA calls for a rookie wage scale. It led to the end of widespread rookie holdouts. However, France took issue with offset language. In the end, he ended up doing right by his client.

What this history tells us: France and CAA are not going to back down. Prescott knows what he wants, which explains the drawn-out negotiations.

• Prescott wants to reset the market in terms of average annual salary, total value, total guaranteed money and cash guaranteed at signing.
• It’s something the Cowboys have resisted over the past several months. But the closer we get to free agency, one side is going to have to blink.
• Based on what we saw with both Donald and Bosa during their holdouts, it’s not going to be France. The ball is almost literally in Jerry Jones’ court.

Negotiating from a position of strength: It doesn’t take a genius to realize that France has the upper hand in talks.

• Fellow Pro Bowler Amari Cooper is slated to become a free agent next month. If Dallas does not come to a long-term agreement with either Cooper or Prescott, the wide receiver will hit the open market.
• France knows this full well. Dallas will place the franchise tag on Prescott should the two sides not come to agreement on a long-term deal, leading to the possibility that Cooper departs in free agency.
• Meanwhile, there’s this whole Patrick Mahomes thing hanging over the Cowboys’ heads. At the very least, the reigning Super Bowl MVP is looking at $40 million annually on an extension this spring.
• While Prescott’s body of work does not compare to that of Mahomes, any deal for the Chiefs’ star will only increase Dak’s value.

Bottom line

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Prescott made the initial power play two years ago when he hired France. Considering the negotiations we’ve seen from the super agent in recent years, hard ball will continue to be the name of the game here.

The Pro Bowl quarterback is now showing outward frustration when it comes to contract talks. Pure conjecture here, but that has to be at the behest of France.

The longer this lingers without a long-term deal in place, the more power Prescott and Co. will have in negotiations. This leads me to believe a deal closer to $40 million than $35 million annually with $120 million in guarantees is in the cards.

Prescott and France have shown their hand. It’s a trio of aces compared to a simple two-pair for the Cowboys. And if they decide to go all in, the numbers are going to be absolutely eye-opening.

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