John had an old hunting buddy, and something happened where the man's son died. I think his name was Trouble or something?

The man kidnaps all three winchesters and he has slips of paper in a bag that John has to pick. He has to pick one of his sons to complete the task on the slip of paper. Sam and Dean both volunteer to save the other but John mostly picks Dean to save Sam. I've been looking for this for a while but can't find it anywhere! Help would be greatly appreciated