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If you are talking about the NFL, NHL, NBA and MLB then the answer is the Chicago Cubs who have not won a championship since 1908.

There are a number of teams that have never won a championship, but the Cubs 101 years without a title is the longest drought.

Coincidentally, MLB has been around the longest.

Longest championship drought in NBA: Sacramento Kings(1951, when the team was the Rochester Royals)

Longest championship drought in NHL: Chicago Blackhawks(1960-1961)

Longest championship drought in NFL: Arizona Cardinals(1947, then located in Chicago)

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Q: What Pro Sports team in the 4 major sports has not won the championship for the longest?
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