Let me offer up a way the addition of Weeden could make sense.
With Tony Romo, Kyle Orton and Weeden, the Cowboys would be set on the position for 2014 and it would probably take them out of picking a quarterback in the draft. The Cowboys liked Weeden coming out in 2012 but obviously not at the first-round level. He is older, but they viewed that as a positive and were not viewing him as a possible long-term replacement.
Things went poorly for Weeden in Cleveland. He deserves blame, but the Browns deserve a lot of blame too. He had two different coaches, two different coordinators and the guy who selected him, Mike Holmgren, was gone too. So there is that to consider. A fresh start might serve him well and I'd have to think Jason Garrett would get a read on Weeden from Norv Turner, who was his coordinator last year.
The Browns have been a place where every quarterback has gone to die, so taking a low-risk, low-cost flier on a quarterback you liked just two years ago makes some sense.
So let's fast forward to training camp and the preseason. Let's say another team loses a quarterback to injury and wants to find veteran help. We can all assume that there won't be a lot of quarterbacks available that can step in and play right away, right?
How high would a guy like Orton be on the list for a lot of teams? He threw for 358 yards and two touchdowns in his only start last year. He played extremely well in that loss; better than anybody ever expected.
If Weeden performs well enough (however you want to define that), then the Cowboys could feel comfortable in trading Orton to a team with a big need at quarterback and get a draft pick in return. Remember, this is Orton's last year under contract. If the Cowboys trade Orton before the season starts, but after July 1, then they would gain $3.25 million in cap space in 2014.
Provided he does not retire, which would be unexpected, Orton is set to count $2.254 million in dead money against the cap because of the two voidable years remaining on his contract. So the Cowboys would gain cap space that they could use to roll over in 2015 and get a draft pick for a player they were not going to keep anyway.
Does that make you feel any better?