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Through the 2008 season, the Tampa Bay Rays have the worst lifetime winning percentage of any MLB team with .417 (742-1037).
Tampa bay rays
Chicago Cubs
The Florida Marlins, they have been to the post season 2 times (1997 2003) and won the world series both times. They were also the first team to win the world series as a wild card
There are 162 games in a MLB regular season. Add that to as many as 36 exhibition games and a possible 19 post season games and MLB team could play as many as 217 games in a year.