I would like to see us trade Romo. I don't know all of the cap ramifications if we keep him past June 1st and then trade him or if we keep him. Personally, I would rather go the Sam Bradford route if feasible...fully intend to keep him unless there's a solid trade request that comes along. Teams get desperate sooner or later and start to make unwise decisions like the Vikings did for Bradford. If not, he can still serve as a very expensive insurance if Dak gets hurt. If that's feasible, I'm all for that plan.
However, since the salary cap came into play in the NFL, time and time again it has shown that free agency is generally a bad idea. High priced FA's rarely work out because they almost never quite fulfill what their contract entails. Sign a high priced FA for 6 years and you may get the equivalent of 4 years of what you paid for...if you're lucky.
That's the biggest problem with high priced FA's, it's not so much the money as it is the money and the length of the contract. That's why the Pats only sign high priced FA's to 1 or 2 year deals...if it doesn't work out they can get out from under that deal quickly. It's why the positive of signing Greg Hardy was that we could get rid of him immediately if he didn't work out. And Hardy was a top-tier player when he came to us. But, it wasn't working out and cut bait with him quickly.
What gets overlooked with the cap and free agency is that you have to re-sign your own talent that you know can play well in your scheme and with your coaches. And it would likely behoove the team to sign Dak to a bigger deal in the next year or two (provided he continues to improve) so they can lock him up and get a favorable deal.
Spending cap money for the sake of it is stupid. There's no correlation between cap money left over and winning in the NFL. It's a mathematical fact. You can only have 53 players on the roster and you have a cap floor and a hard cap ceiling.
And every step of the way where he have tried a 'win now' mentality...it's failed miserably. A 'win now' mentality meant a flop in Greg Hardy. A win now mentality caused us to sign a ridiculous deal for Brandon Carr and he's not nearly the money we've given him. A win now mentality caused us to trade away a pick to get Mo Claiborne and he's performed nowhere near that.
Back before the 2006 season, Ryan Clark became a free agent after a successful season with the Skins. The Steelers went more after Clark than they do with most FA's, especially since Clark was considered a run-of-the-mill player. Meanwhile the Skins were infatuated with high priced FA Adam Archuleta because they like shiny things.
The Steelers ended up getting Clark and they wanted him because while he was a bit of a run-of-the mill player, he fit perfectly into their system and gave them what they needed...a safety that can direct Troy Polamalu around and put him in the best position to make plays. Clark ended up playing 8 seasons with the Steelers and was a nicely productive player that helped Polamalu become a future HoF'er.
Archuleta became the highest paid safety in the league, started 6 games and was cut after 1 season. We have tried the 'shiny things' method in free agency and it has always come back to hurt us. That's the thing about Free Agents....there's usually a good reason as to why their former team doesn't want them no more. If they are a high priced FA, there's inherently more risk that his former team didn't think was worth it. With a lower priced FA, those are guys that are more likely to have slipped thru the cracks or they had to be let go because his former team signed some expensive FA to do the job.
Outside of QB, a high priced FA is almost never worth it in the end.
YR