Trading Dak Prescott this season would add about $10.5 million to what the Cowboys already have against their 2027 salary cap for him. They would still have to pay for his replacement, but the cost of this endeavor deserves a closer look.
I could accept a rough 2027 if Dallas came out of it with draft picks, a younger quarterback and Dak’s existing contract off the books. Before we even get to the Chris Simms comments, I don’t know how much longer Jerry Jones keeps this team together thinking they’re close.
I can’t and won’t blame Dak Prescott for every loss and give that as the reason we need to move on. I want to know whether Dallas can build a better team with the picks and eventually have some financial flexibility that a trade could provide.

The Money Wouldn’t Stop Me
Chris Simms had this to say on his podcast “Chris Simms Unbuttoned”:
“There’s been some murmurs that in Dallas that they’re a little bit like at the end of their rope with Dak Prescott like it’s like things better turn around or he
A trade this season would leave us seeing about $86.48 million in dead money on Dallas’ 2027 cap. His cap charge is now roughly $76 million, making the increase to about $10.46 million before paying a replacement.
Unless Dallas pays additional money to complete the trade, Dak’s existing contract would leave no cap charge in the 2028 season.
Would there be saving now? Not really, Dallas would have approximately $41.71 million in allocated bonuses on its 2026 cap, plus salary earned. Only the remaining unpaid base salary would come off the books.
Here’s the big thing: Dak Prescott would have to approve the trade.
Could I accept the 2027 hit for a good return? Yes, but Dallas is going to have to pay those bonuses, and eventually they will have to finish counting them against the cap.
Trading him now would be the best scenario because the Cowboys could use the draft picks in the upcoming draft. Waiting until after June 1st would spread the bonus out across 2027 and 2028, but that doesn’t help for the 2027 season.
If Dallas wants a Prescott trade to help find his replacement in the 2027 NFL Draft, they need to get the timing right.

The Cowboys Top Pick Belongs to the New York Jets
As we enter Week 9 of the NFL season, Dallas’ own first-round pick projects to be at number 10. However, that pick is going to the Jets as part of the Quinnen Williams trade.
The Cowboys get to use Green Bay’s first-round pick in the upcoming draft, which is sitting at number 20 right now. Then Dallas’ second-round pick is sitting at 45.
We get to watch a losing team, and somebody else gets the better draft pick.
This is what makes the return on a trade for Dak Prescott that much more important. I would like to see them get two-first round picks, but just because another high-profile quarterback got that a few years ago doesn’t mean it will happen again.
I’m curious what other teams would be willing to give up for Prescott.
We all know moving up from number 20 in the draft would get expensive, but I wouldn’t trade him and use every useful pick trying to replace him because his replacement will need help too.

Sam Howell Would Get the First Shot
If Dallas traded Dak Prescott this season, I would start Sam Howell and use the remaining games as an audition for next season.
Howell won the backup job, so he should know the offense, but his contract expires after this season. Maybe we could see Howell earn the 2027 job. More importantly, it will tell us if we need someone different next year. I’d like to find out before free agency.
Mac Jones would be my next call. His contract is scheduled to void in 2027, and I’d be interested in a short deal, but we aren’t getting into a bidding war for Jones.
The fallback choices would be Geno Smith and Gardner Minshew, who just beat us Sunday, from the potential group of free agent quarterbacks. Anthony Richardsona and Tanner McKee would also interest me for the short term if the first choices aren’t there.
Kyler Murray and Tua Tagovailoa would be interesting, but would be to expensive for a stopgap player. I’m not trading Dak just to get stuck with another veteran quarterback with a big contract.
My choice is to keep the veteran cost at a minimum and have room for Dallas to draft and develop somebody.

Drew Mestemaker Has My Attention
I have watched Drew Mestemaker in person, and he lives up to the billing he is getting from sports analysts. The Poke received 17 of 25 votes in Pete Thamel’s recent ESPN poll asking scouts and executives which quarterback would be selected first.
Following him was CJ Carr with four, Darian Mensah with three, and Dante Moore with one.
There is no way Mestemaker falls to 20, but if Dallas believes he can be the next franchise quarterback, I would be interested in moving up for him. I think I would rather start Howell and not give up multiple first-rounders just because the quarterback spot is lacking.
Carr and Mensah could get close to 20 and Moore would need some serious medical assessments after a concussion ended his season. The thing is, all four can stay in college and just collect a paycheck there too.
I could live with waiting for the right quarterback, based off of the new coach’s choice. I don’t want Dallas to take a quarterback just because they feel forced after Dak.

Jerry Would Have to Follow Through
Would there be a Sunday when we missed Dak Prescott? Absolutely, but that is what happens when you move on from a franchise quarterback. I could accept it if the Cowboys got a good return for him and gave the next quarterback a fair shot.
The number one thing would be choosing the coaching staff. Let the coaches pick the player they can work with and like and keep enough draft capital to fill the team around him.
If that means Howell starts in 2027 while the Cowboys take on the cap hit of Dak, so be it. We are having a losing season with Dak. Having one without him would be much easier to stomach.
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