QB is the most important position and often has the highest cap value. Romo did a couple of season but most he actually didn't. You may be forgetting how poorly we managed the cap during his tenure.
https://www.spotrac.com/nfl/dallas-cowboys/cap/2017/
Bailey was cut for cap purposes because he had declined as a kicker and we could get at least the same performance from Maher for much less. If Romo isn't injured Prescott never sees the field. Totally different scenario.
Now I agree that we have a window right now to win while Prescott is on his rookie deal, but we really aren't getting the full benefit of it. We were still paying for Romo for some of his time and now Jerry is talking about extending him already. So this would look like the year where "value" is relevant. I'm not sure Prescott is good enough yet.
I'm very aware of the cap mgmt and mis-mgmt much of it led by paying Romo "Payton Manning money".
The SB QBs have often been cheap cap hits.
Last year Brady and Foles combined to earn ~19M. 6M less than Romo would have earned alone.
Romo priced himself out of the team's plans and the league essentially.
Same reason Indy gave up on Payton.
At QB part of being a leader is being cap friendly.
If Dak comes in under 25M long term this team will be set at QB for a long time.
If he wants to play hard ball and negotiate for every cent we will be strapped, win less and he likely gets axed eventually.
Money is important in real life and even more important in the NFL.
Top 10 QB cap hits in 2018"
1. Jimmy G --team ousted
2. Stafford --team ousted
3. Derek Carr --team ousted
4. Flacco --benched and replaced by cheap QB. play has dropped off big time since he was paid.
5. Luck --fighting for playoff berth.
5 NFL R1 drafted QB are starting from the 2018 class because money matters.
Aaron Rodgers is truly a legend but he's not worth 20M more than Dak Prescott per year.
More of these guys need to be like Tom Brady.