This man should have gone out while he was on top. He had two recent World Series championships and was the star of the bloody sock myth. He was a great pitcher who was getting old and should have retired at the end of last season.
But he kept going. He insisted on coming back this season and got hurt. Now he had to have surgery and is out for the rest of the season.
He now has two choices: end his career on the Red Sox disabled list or attempt to come back next season after he has healed from surgery. Neither are attractive choices.
If he ends his career now, he went out as a washed up and hurt old pitcher who tried to outlive his prime. He will not go out with a bang. If he tries to play again next season, however, after the surgery, time off, and another year added on to his age, he will most likely not be pitching his best and will probably not play with the Red Sox.
Curt Schilling should have left after the 2007 World Series victory and left the game on top, but what kept him there? I don't think it was to make more money. My guess would just be that he got glory hungry. The fantastic career he had just wasn't enough for him and he needed more. His greediness ultimately ended poorly, with him not playing for the remainder of this season and having a tough choice to make next season.
I think he will keep being greedy and will continue to play next season. He will end his career when he is not pitching at his best for some second rate that could never compare to the Red Sox and the memorable victories he pitched for them.