The Browns trade of Kellen Winslow was the right thing to do in just about every scenario, based on two factors:
1) They had no intention to redoing his contract prior to or during this season
2) K2 has a history of injuries
The Browns were left with a couple of options, assuming they weren't going to resign him.
1) Let him play out the season, and then franchise him the following year with the intent to either trade him or keep him for another season
Why this doesn't work: This puts all of the risk on the Browns with very little reward. If Winslow plays well, maybe they can make the same deal that they made with the Bucs one year later (after franchising him). If Winslow gets hurt, which is likely, the Browns lose any possible trade value that he had.
2) Let him play out the season, and let him go as an unrestricted free agent, especially if he gets injured. This is the San Diego Drew Brees plan. It assumes you have no idea if the player will be good the following year, and if he is, you'll likely get a compensatory third-round pick from the league (like San Diego did for Brees)
There are third points to keep in mind regarding Winslow. First, Savage (and it seems Kokinis and Mangini as well) believe Rucker has the ability to be a legitimate receiving tight end in the NFL. The unfortunate aspect of this is that Romeo didn't give Rucker the chance to prove himself this year.
Second, and more important, the Browns played their best offensive game of the season against the Giants WITHOUT K2. Hieden provided the in-line blocking needed (as did Tucker in his only game of the season), and the team looked great.
Third, Jurevicius is back. This takes an enormous amount of pressure off Braylon to be the "go-to" third-down receiver. Joe also has the ability to play opposite Braylon near the goal line and run a fade route.
In summary, the extra No. 2 for Winslow is huge, the No. 5 is a throw in. . . next up, moving DA for a late No. 2 or early No. 3 (Detroit, I'm looking at you).