It's really tough to build a winning dynasty in Major League Baseball, this much we know. Reeling off a streak of winning seasons is hard enough, never mind stringing together multiple World Series victories. So many teams came close to achieving immortal status only to fall short that we rolled out an entire series on failed dynasties.
Building a lasting loser, though? That's a lot easier. The Baltimore Orioles, Pittsburgh Pirates and Tampa Bay Rays are riding streaks of 10 or more losing seasons. Add in the Royals and Expos/Nationals, and those five teams have combined to post 54 losing seasons in 55 tries. Forget failed dynasties. These are the failure dynasties.
Two teams made a strong case to be included in our feeble five. The Milwaukee Brewers haven't tasted the postseason since 1982, the second-longest playoff-less streak in the game. From 1994 to 2006, the team never finished above .500. The Brewers finished last or second-to-last seven times in those 13 seasons, including three straight years in the cellar from 2002 to 2004. But Milwaukee's now a team on the upswing, coming off 83 wins and a second-place finish, with a core of young talent that's expected to contend for a division title. The Brewers are exempt.
The Cincinnati Reds own the fifth-longest streak of losing seasons, with seven. Counting Ray Knight's one-game tenure, five managers handled the reins in those seven seasons, either in permanent or interim positions. That seven-year itch included a three-year stretch in which the Reds' arsonist pitchers were last in the National League in park-adjusted ERA. But Cincy misses the cut, partly because of optimism toward a team that suddenly looks like a contender, but mostly because Kansas City, despite a more recent winning season, has a more impressive track record of losing.
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