If Schilling was smart he would retire from the game. He’s got 3 WS rings, a playoff resume to kill for and a huge amount of gratitude for the fans. To go somewhere else for one more shot at glory is nothing more than ego.
Heed the warnings of Roger...
From what I've read Schilling is a huge asset in the clubhouse, giving advice to young pitchers and helping them with many aspects of the game.
I wouldn't compare Clemens with Curt, he loves the game, thinks he can still play baseball and help the team.
To the best of my recollection he hasn't retired three times to load his pockets.