Too many.
The Baltimore Orioles?
From 1901-2012, the Detroit Tigers have had 44 losing seasons.
No, we're bad :-(The Orioles have spent the last 12 seasons as a losing team. This has been called "transitional periods" and "rebuilding phases." The Orioles fan base has been decreasing as a result (only the strong survive).
20
78
Too many bro.
Between 1962-2011, the Mets have had 27 losing seasons (W/L pct below .500) and 23 winning seasons (W/L pct above .500).
The Dallas Cowboys did not have a losing record from 1965 to 1985 -- 21 seasons. During that period, they appeared in the playofs every year except 1965, 1974 and 1984.
21 Games,1988
as of September 8, 2008, the pirates lost their 82nd game making this year their 16th consecutive losing season
Pittsburgh pirates 19 seasons
21 ... the Orioles lost the first 21 games of the 1988 season.