1939 St. Louis Browns (43-111-2) 5

Quite possibly the worst all-time Browns team, though there's plenty of competition. Other than a few successful winning years in the first decade of the 20th century, the 20's, and during WW2 when they managed to win a rather dubious pennant, this team may have been the least successful team in baseball history, generally languishing at or near the bottom of the standings. They won the pennant in '44 and came in 2nd in '02 and '22. Other than that, they rarely posted a winning record. Attendance was usually poor, and they had no real chance at catching up with more well-heeled franchises, which should sound familiar to current fans. Generally, they had to sell or trade players to stay afloat financially. They moved to Baltimore in the 50's.