1932 Boston Red Sox (43-111) 5

Statistically the worst Red Sox team ever, though perhaps if you carefully examined the roster, you might find that a 20's team was even worse. They had a few decent players, such as a guy named Dale Alexander, an early season pickup from Detroit, who actually wound up leading the league in batting average, but mostly fourth rate guys and has- beens that had no realistic chance at competing against the powerhouses in New York and Philadelphia. Terrible hitting and pitching. In the 20's and 30's, this team had very bad attendance, even worse than the crosstown (and generally almost as bad) Braves had, and severe financial woes.