In 1992, the Pittsburgh Pirates went 96-66, won the National League East and played the Atlanta Braves in the NLCS before losing in Game 7 (see also: Bream, Sid). That was their last winning season.
2009 marked the Pirates’ 17th straight losing season, a record not only for MLB, but also for any North American sports franchise. The closest they have come to a winning record was in 1997, when they finished with 79 wins (just two games below .500).
With a team payroll that routinely ranks near the bottom of baseball (in 2009, they had the smallest team salary in MLB, at just $25.2 million; by comparison, Alex Rodriguez made $33 million), the Pirates’ streak is one with no end in sight.
Image via The Curse of Bonds