As free agency nears, the Dallas Cowboys and quarterback Dak Prescott appear headed to an offseason contract battle. Prescott just finished his best season statstically as an NFL quarterback in his fourth and final year of his rookie deal.

Dak is set for a huge pay increase even though it has been reported that he is headed for the franchise tag. The franchise tag would pay him almost $27 million for the 2020 season. Prescott made it known that he does not plan to attend offseason workouts if a longterm deal is not reached before then.

The Cowboys have done nothing but praise Dak in the media anytime a question is asked about his longterm future with the team. Stephen Jones recently said that, “Things were fixing to heat up,” after talks ended after Dak reportedly turned down $33 million before the season and asked for more after his hot start. 

There is an extra layer to the conversation that has emerged since the season ended and Michael Irvin added to the conversation this weekend by saying that he heard from “significant people” that the Cowboys were having discussions about trading Prescott and signing Tom Brady. 

Okay, so lets think about that for a second. 

The Cowboys are thinking about trading a 26 year old quarterback that is coming off a career season for a 42 year old quarterback coming off his worst season in a lot of statistics. 

I am probably going to ruffle some feathers here, but I am not against the idea of franchise tagging and trading Dak for two first round draft picks or a first and second and signing a vet quarterback for 1-2 years while continuing that search for the “special” or “elite” talent.

The biggest reason I am willing to have this conversation is that I don’t agree that a team has to pay a “good” quarterback elite money just because everyone else is doing it. I believe a team out there will ditch that philosophy and be better off because of it. 

The intangibles for Prescott are there. There is one intangible that I have not seen from him and that is the ability to elevate those around him and the 2019 season is a prime example and I’ll tell you what I mean by that.  

The Cowboys had one of the most talented rosters in the league with Dak having a career season and the team went 8-8. You can come up with all the reasons you want, but the reality of the situation adds up to 8-8 and missing the playoffs in a very winnable division. 

In a division deciding week 16 game against the Philadelphia Eagles, Prescott went 25-44 for 265 yards and no touchdowns in a game the Cowboy lost 17-9. The Eagles were down their top three receivers and lost their star tight end early in the game. 

I promise you I realize it’s not all his fault. But at some point, you have to step up and make a game deciding play as a franchise quarterback. 

I am not just giving Dak away so I would want at least one first round pick and possibly two depending on the draft position of the other team. 

Now, you might ask, “What team is going to trade two 1s for Dak?” I have three teams that could be interested. 

Los Angeles Chargers – After a disappointing 5-11 season in 2019, the Chargers will be in the market for a quarterback after parting ways with Philip Rivers. They hold the 6th pick in the draft. 

My asking price: First round pick plus two second round picks. 

Las Vegas Raiders – The Raiders have Derek Carr under contract until 2023 but appear willing to move on from Carr as they head from Oakland to Vegas. The Raiders have two first round picks (12th and 19th) and could package those up for a quarterback. 

My asking price: First round pick, two second round picks. 

Tampa Bay Buccaneers – At this point, it is unclear on whether the Bucs are going to move on from turnover machine, Jameis Winston. Despite finishing 7-9 in the NFC South, there is a lot to like and maybe a quarterback who isn’t as careless with the football could unlock the teams potential. They have the 14th pick in the draft. 

My asking price: 2 first round picks, second round pick. 

Now, if the Cowboys were able to find a trade partner for Prescott, what happens next? Who plays quarterback? I will give you a few options. 

(Disclaimer: I am not saying the options below are better than Prescott, but signing one of these guys to a shorter term contract will allow you to keep a team around the quarterback) 

Free Agent Targets 

Tom Brady – Not realistic to me because I don’t believe he leaves New England. If he leaves, I would consider it for a year or two. I mentioned earlier that he’s coming off one of his worst statistical seasons but I believe a big part of that was related to offensive talent around him. 

Andy Dalton – Don’t laugh. While I don’t think he’s better than Dak, he’s not.  I do think he is capable of managing a game with the talent the Cowboys have. He was able to make the playoffs four times in Cincinnati before the wheels fell off with Marvin Lewis as head coach. 70-61-2 record as starting quarterback. 

Cam Newton – Newton is expected to be released by the Carolina Panthers. Newton is a very intriguing name to me. Newton will just be 31 in May and has won an MVP award and led his team to a Super Bowl. Biggest question is health, which is obviously important. 

The other side of this is maybe you just go with another rookie quarterback and give him the same tools you gave Prescott and try to strike while that quarterback is still on his rookie deal.

It has been proven for almost a decade that the way to win a Super Bowl in the NFL is to have a quarterback on a rookie deal (Seattle, Philadelphia*, Kansas City), an all-time great quarterback making less than the market says he should make (Brady, Peyton) or an elite defense (Denver). 

(*Nick Foles led the Eagles to the Super Bowl after Carson Wentz when down due to injury)

Now, at some point will a quarterback that gets paid win a Super Bowl? Probably so. 

Is Dak the quarterback to do that? That remains to be seen. 

At the end of the day, I believe that the two sides will agree to a deal but I think there is a conversation worth having until a deal is signed.