Sydla
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For me it comes down to principle, I simply would not hand him off to a contending team for a measly 5th round pick. Here's the benefits of releasing him.
http://www.sportingnews.com/nfl/new...salary-cap-cowboys/1dbh9ldnydf191ik04iqu21ius
The benefits of releasing Tony Romo
"There are two ways in which releasing Romo makes more sense. One is the immediate cap relief the team would realize if Romo was processed as a normal release. He is currently slated to count $24.7 million against the Cowboys’ cap, and the team will be about $10 million over the projected cap next year if Romo is on the roster. All teams must comply with the salary cap on the eve of the first day of free agency, and Dallas would be able to free up $5.1 million as early as February by cutting Romo before free agency begins.
Such immediate cap relief would not be possible with a trade, which can’t be processed until the first day of the new league year … at which point the Cowboys already would have needed to be salary cap compliant. That means they would need to have restructured contracts to make up that $5.1 million Romo would have saved them, which can create future salary cap headaches."
Here's the benefits of trading him.
The benefits of trading Tony Romo
"While trading Romo would not give Dallas immediate cap relief, it would accomplish two important things: getting a draft pick and controlling where Romo lands.
Nothing reflects worse on a team than having to cut a high-priced player and receiving nothing in return … especially if that player can still play. If Romo were to have a good season elsewhere while Dallas kept a large cap charge for him, the organization would be raked over the coals by media and fans.
And it is possible a player like Romo — if he has a successful season elsewhere — could return a second-round draft pick, which is a decent consolation prize."
At least you admit this is nothing more than your bizarre principle at work here. Because there is no logical explanation for suggesting letting Romo walk for nothing is better for the team than taking back even a low round pick.
And the Cowboys are now cap compliant so there's no benefit now in terms of the cap in trading or cutting him now.