I like Romo. That said:
Al Davis -> Carson Palmer; Jerry Jones -> Tony Romo
Everyone knew that Oakland overpaid for Palmer, and the reason was clear- Al Davis knew he didn't have long to live and wanted to make one last push for a title. Jerry Jones is no spring chicken himself, and if he wants to build a new contending team from scratch he needed to start yesterday. I never blamed Romo in the past for all the 8-8 or 9-7 seasons, but pretty soon, they'll be having mediocre seasons because of Romo instead of having them despite him.
Here is what I hate about this deal. Tony Romo would have been a free agent next year. He would have hit the market a month before his 34th birthday. What's the going rate for a 34 year old QB, especially one with Romo's image problem? I'm thinking if Romo had been available in open free agency, you're looking at Kolb money, max.
Instead, they pay him close to Manning/Brees money, on a deal that keeps him under contract until he's almost 40. The soonest they can get out of the contract without eating dead money is 2019, Romo's age 38 season.
I've defended Jerry Jones many times, but this was a big mistake. At the very worst, you could lose Romo next offseason and still draft a QB like Manziel, Bridgewater, or Boyd in the 2014 draft by moving up. This was not only a poor long term decision, but a poor use of resources, IMO. If you are willing to give Romo that kind of money, you could at least wait til UFA because no other team would offer money like that.