Dak Prescott’s window to win a Super Bowl with the Dallas Cowboys has closed | Opinion
Door No. 1: $74 million.
Door No. 2: $23 million.
Door No. 3: $23 million.
Those haunting totals represent the “dead cap” money figures attached to quarterback Dak Prescott if the Dallas Cowboys were to release him, in order, after the 2026, ‘27 and ‘28 seasons.
(To cut him before June 1 of ‘26 requires a number so high don’t even consider it.)
Just prepare that Dak is this team’s QB for the next two, and more likely, three years.
Given his age, 32, and the state of the current roster, his chance to win the Super Bowl as the starting quarterback of the Dallas Cowboys is the same as Jerry Jones selling the franchise. Vegas lists the Cowboys’ chances to win the Super Bowl at 60-1.
As the Cowboys kick off their season tonight in Philadelphia, we will be watching a player who is playing out the string.
Unless the Cowboys dramatically change their philosophy and attitude about “dead money,” and how they build their roster, their ceiling with Dak over the next three years is not that much different than his first nine years in the league.
Mood around team like Dave Campo era
The mood and expectations for this team have not been this bad since the final season of the Dave Campo era. Disgusted. Resigned. Indifferent.
Campo’s last year was 2002. Since the first year under coach Bill Parcells in 2003, the Cowboys always had something going for them in Week 1 to keep them out of the dreaded “top pick” conversation.
It was Parcells. It was the discovery and development of Tony Romo. The same for Dak Prescott. Since ‘03, the Cowboys have ranged from good to having a “real chance.” Since ‘03, they’ve had but five losing seasons.
At best, this version of the Cowboys under first-time head coach Brian Schottenheimer is a playoff team. There is still first class seating in the NFL, and the Cowboys remain in coach. Neither are they in steerage, nor in seat 32D next to the toilet.
The Cowboys just traded their best player to the Green Bay Packers in exchange for one player and two first-round picks. Those picks will be rookies in ‘26 and ‘27; as such, they won’t make a dramatic impact until ‘28. Best case.
Given this franchise’s reluctance to add top talent in free agency, their draft-and-develop approach can work, but requires time.
Hard to fathom, but Dak’s best chance to reach the Super Bowl came in his rookie season, when the Cowboy lost to the Packers on a last-second field goal in a 2016 NFC divisional round game. The Cowboys were the top seed in the NFC that year.
Two other times Dak led the Cowboys into the divisional round, in ‘18 and ‘22. The ‘18 loss to the Rams in L.A. was not close; the ‘22 defeat against the 49ers in San Francisco was.
We didn’t know how good we had it.
No Russell Wilson solution
No one believes in Dak more than Jerry Jones, and no team hates “dead money” more than the Cowboys.
Cowboys fans hoping the team flushes Dak, the way the Denver Broncos did with Russell Wilson, are better off hoping for a Texas snow storm in July. In March of ‘24, the Broncos waived Wilson, which required an $85 million salary cap penalty.
Denver coach Sean Payton was done with Wilson, and the Broncos survived the hit. In the first season after cutting Wilson, the Broncos reached the wild-card round with rookie quarterback Bo Nix, the 12th selection in the ‘24 NFL draft.
To follow this path, it will have to mean a few things the Cowboys historically don’t do: Absorb an enormous salary cap hit, and select a quarterback in the first round.
The scars of the Troy Aikman to Tony Romo years run deep with the Cowboys, and Jerry has repeatedly demonstrated he’d rather be in the conversation for the playoffs than in the chat room for a top pick in the draft that could be used for a quarterback. For Jerry, developing a rookie quarterback takes seasons, and time that he doesn’t have.
He prefers a chance at 12-5 and the playoffs than 5-12 and a top-10 pick.
The only way this team moves on from Dak earlier than ‘27 is if he is historically awful, or his body no longer can hold up and he is forced to retire. Since the start of the 2020 season, his injury history is well-documented and now officially a point of concern.
Dak Prescott is the Cowboys’ starting quarterback, and the team will remain around the conversation for the playoffs. Nothing more.
To do something else would require them to walk through a door that is too expensive for them to even consider.
