Most players don’t go out on top. Likely because most players don’t want to leave with something still left in the tank or they simply don’t have enough left in the tank to leave at the pinnacle of their respective sport. In the case of Derek Jeter, his storybook career would suggest a sixth title could technically be within reach. Yet if past is prologue, in the lore of the New York Yankees, Jeter would be hard pressed to find some company in this class of players going out on top.