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It happened in 1981. The Kansas City Royals were 50-53 in a strike shortened season. Since it was played as a split season, the first-half and second-half winners of each division made the playoffs. Interestingly enough, the Cincinnati Reds had the best record in the majors and the St. Louis Cardinals had the best record in the NL East, but both of those teams did not qualify for the postseason.

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Q: Did a MLB team that finished under 500 ever reach the playoffs?
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