It happened once before, a long time ago.
In the summer of 1966, the Red Sox were a bad team. They finished in ninth place with 72 wins and 90 losses, 26 games behind Baltimore, who won the AL pennant and then swept the Dodgers in the Series.
The following year, as many will recall, was the so-called “Impossible Dream” season. With new manager Dick Williams barking orders and Carl Yastrzemski playing out of his mind, the Red Sox were 92-70, won the AL pennant, and took the Cards to seven games in the World Series.