I don't think they want to go into the season without a deal in place.
If you look at all of the spin coming out about Prescott in OTA's and Moore's plays making the players happy and add to that the most optimistic owner in the NFL, they get the deal done before camp. He doesn't want anything but a forward lean going into the season. And the FO wants to shut down the Dak talk before camp and get everyone resigned to the reality.
However, having said that, they don't know this forum. We still have posters complaining about what they paid Romo 5 years ago.
Definitely possible. Way I see it, Dak has way more tape than Romo in 2007 when they first extended him during the bye week.
However, this deal will be massive, and I think with Stephen having more say into the contracts now they very well could go back and forth with his agent for a long time, similar to D-Law's situation. If it wasn't for his shoulder surgery timeframe, or D-Law siding with SJ on the phone, that saga could still be ongoing now, like the Clowney situation.
This time of year there's always a positive spin in Big D. Hell, we had positive spin on guys like David Arkin and Bill Nagy during MC/TC years ago during their rookie year.