You're forgetting Romo's first big contract in October of 2007, halfway through the 2007 season and barely a full year with Romo as a starting QB since the midway season point of 2006. It didn't hurt the team then. The problem with his second big contract in 2013 is that the whole Oline was decimated and in need of being fixed with better Olinemen, which it started to with the drafting of Tyron Smith, followed by Martin and Frederick. Big contracts for your stud QB can work if you draft well and smartly in each draft. The most important piece to any successful team is their QB, not their RB or some other player. That's where Jerry messed up recently.
The problem with Romo's 2nd big contract was Romo.
He was hurt.
He couldn't practice and even when he was sharp the rest of the offense wasn't because the other guys didn't have him to practice with.
The difference between Romo and Dak is body type.
Romo was a fairly normal human being physically.
It's why he went undrafted.
He's maybe 6'1" and 210 today.
He probably played up a bit to 220-225 at peaks.
Dak is simply as bigger dude. He's much thicker in the legs and carries at least 20 more pounds of muscle.
All that said, Dallas had no real choice.
You don't not pay a franchise QB.
You pay him and do everything you can to win. They did and came up short in key moments.
The Cowboys beat the GHiants twice int he regular season fairly handily and lost on a tragically bad play by a WR in the playoffs... that Giants team de-throned the undefeated Pats to win a SB....
Then you had the Dez catch game which was an appalling call. The ball NEVER touched the friggin ground outside Dez's control.
Two legit shots to win titles are definitely worth paying out franchise QB money.
The alternative is be Cleveland.
Go get a top QB early in draft and be everyone's next year team for a few seasons before starting over.
Dallas fans are both unrewarded but also spoiled.
They have only seen one year of bad football when Romo was out all year.
Having a franchise QB does that for you and they went from one directly to another.