Making any kind of sense what Jerry and son are going to do, is an effort in lunacy. If you look back at everything they have said over the last two months, you get absolutely nothing that leads anyone to believe who they are targeting in the draft as well as if they are going to extend Dak (Lamb or Parsons also for that matter), or let Dak play out his last year or trade Dak to a team like Minnesota or Las Vegas. It is nothing but a crap shoot at best.
We know Jerry is a business man, and a damn good one or else the Cowboys wouldn't be the richest franchise in all of sports nor the most talked about. The media lives off the Cowboys literally every single day because no news on the Cowboys is even news. So from just a business point of view, definitely not a football point of view, it makes literally no sense for Dallas to let Dak to play out the year on his contract and get only a 3rd round choice in 2026. Regardless of what fans think about Dak, the NFL and GMs and Coaches see him as a top ten QB so you aren't going to let him go for a 3rd two years down the line from a business point.
So that really leaves just two options, extend him at most likely the top of the market price or trade him draft day to a team that is willing to give you close if not more than you want. And we know that Dak has to agree to that trade or it is a no go and there lies the biggest problem because the trade would only happen if there is a contract in place for Dak (extension). So anyone's guess is just that, a guess.
The only difference I see in the Dak situation than the last time we sign him to a big contract was that his agent let it be known what Dak would sign a new contract for in terms, and this time we haven't heard anything from his agent and really nothing from Dak other than it will get done on a new contract. Don't remember him saying a new contract with Dallas, just a new contract. So the tea leaves are still murky. The only thing that would tell us something, is if any of us really knew what they think of Trey Lance, then pieces could come together rather quickly.
So 10 more days to see what is going on with Dak, but for me, if Dak is still on the Dallas roster after the 1st day of the draft then I believe that they are going to extend him, like it or not. It just makes business sense not necessarily football sense.