The Pittsburgh Pirates of major-league baseball will have a losing season this year, thus extending the team's string of losing seasons to 16 (1993-2008) and tying the dubious record of the Philadelphia Phillies (1933-1948).
The leading consecutive-season losers in other major sports are, as far as I can determine, the Tampa Bay Buccaneers of pro football (15 seasons, 1982-1996), the Kansas City/Sacramento Kings of pro basketball (16 seasons, 1983-84 through 1998-99), and the Vancouver Canucks of pro hockey (15 seasons, 1976-77 through 1990-91).
The Pirates seem destined to set a new record for consecutive losing seasons among major sports teams.
The all-time major-league record for losing is held by the San Diego Padres. The Padres have compiled an overall W-L record of .462 since the team's inception in 1969 -- the worst record of any franchise formed before 1978. The Padres nevertheless have managed to win five division titles, and have twice gone on to win league championships.
The expansion Washington Senators/Texas Rangers -- a 1961-vintage franchise -- have an overall W-L record of .468. That is the second-worst record among franchises formed before 1978. The Rangers "boast" but three division titles and not a single league championship.
In spite of the "accomplishments" of the Padres and Rangers, I must grant the Worst Franchise Award to the above-mentioned Philadelphia Phillies. The Phillies, who are now in their 126th season of major-league play, have compiled a W-L record of only .470. During the 31-season span of 1918-1948 the Phillies eked out only one (barely) winning season, going 78-76 in 1932. (The Pirates have an overall record of .505, in spite of a long losing tradition, one that dates back to the second season of their 127-year history.)