Dak Deal Doesn’t Get Done; Bears, Colts Could Not Be Happier

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Dak Prescott and the Jerry Jones-led Dallas Cowboys were unable to come to an agreement on a contract extension. This led Prescott to sign a franchise tag that will pay the quarterback $31.4 million in 2020.

The Indianapolis Colts, Chicago Bears, and perhaps a few other teams should be chomping at the bit. 

This offseason, Indy signed Philip Rivers to a one-year deal worth $25 Million. Hefty investment for the short term, but frees the team up just in time for when the Dallas Cowboys drop the ball with Dak Prescott.

The Cowboys organization raved over the years on Prescott’s attention to leadership and preparation. No team needs a leader who obsesses on preparation like Indianapolis, the 7th youngest team in the NFL. 

A young team in the NFL goes hand in hand with financial flexibility and the Colts ability to dominate draft day under general manager Chris Ballard lent them the flexibility they’ll see in the 2021 offseason. This makes the marriage between Prescott and Colts’ head coach Frank Reich inevitable.

The Cowboys have never hesitated to pay their superstars as Zeke Elliot, Amari Cooper, and Demarcus Lawrence all received contract extensions. Cowboys owner Jerry Jones failed to come to an agreement because he sees Dak on a different level than Patrick Mahomes. The Cowboys were reported to have offered a contact that would pay Prescott $33-$35 million annually at $100 million guaranteed. 

Likely harder to accept that offer when Patrick Mahomes just agreed to a 10-year contract at roughly $450 million. 

The Indianapolis Colts are in a much more flexible position, financially, to absorb Dak’s asking price. Their young roster can benefit most from his leadership and obsession to get better. 

The Colts roster is filled with young guys looking for a leader, meanwhile Cowboys star Zeke Elliot is arguing over ESPN reports claiming he’s the third best running back in the NFL. A praise hungry running back begging for the ball will do nothing to help Prescott land his deal in Dallas.

The Chicago Bears are another team frantically trying to lock in a long term solution at quarterback. Most fans believed their trade for Super Bowl MVP Nick Foles punted their ability to pursue future options, but their ability to restructure his deal to 3-year $24 million changes everything.

If the Chicago Bears see a fit with Dak Prescott after the 2020 season, they should be able to dance around financial constraints to get a deal done. $31 million in cap space next offseason that climbs over $100 million the year after doesn’t hurt their case for Prescott, either. 

Nick Foles and Mitchell Trubisky have proven to be liabilities either for their play or inability to stay on the field, so a more reliable Dak Prescott should be enticing. 

The future for Dak Prescott should reside outside of JerryWorld where he can take advantage of a young roster in Indy or be the missing piece to a championship roster in Chicago.

Written by Gary Sheffield, Jr

Gary Sheffield Jr is the son of should-be MLB Hall of Famer, Gary Sheffield. He covers basketball and baseball for OutKick.com, chats with the Purple and Gold faithful on LakersNation, and shitposts on Twitter. You can follow him at GarySheffieldJr


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  1. I know it’s the Cowboys, so everything is news there, but Dak isn’t all that great. He is a starter, but how do the Cowboys increase in salaries improve all the guys getting over-paid?

    If Dak couldn’t win last year with all the ‘weapons’, how does his new huge salary, Amari’s salary and Zeke’s new salary (combined $50 million for this year) make them better this year. Assuming they play this year?

    NFL is in big trouble with the social justice garbage and kneeling, but some teams may sigh in relief and the Cowboys May be dodging a salary cap bullet.

  2. That’s all well and good but Dak Prescott is no Patrick Mahomes. Dak and his agent are overvaluing his talent. The Cowboys have the most talent year in year out in the weak NFC East and don’t consistently win the division or any playoff games. Dak is good but not worth more than $25-30M per season tops, in my humble opinion.

  3. Jerry is right on this one — but he will be demonized by NFL players for “disrespecting” Dak. He will also be called a racist, given his relationship with Tony Romo and for bringing in Andy Dalton. Dak is a very good guy and team player but only an average QB. $33mil per year and $100mil guaranteed? That’s above market for an average QB. So you can’t say Jerry favored Zeke and Amari over Dak.

  4. This Dak Prescott contract is the perfect sports story, absolutely fascinating. I don’t think there is another story with so many facets. I hope for chaos-Dak to hit the open market next offseason. So far so good. Next target- Dak and/or the Cowboys have a mediocre season.

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