Who has the longest MLB drought?

Answer 1

the Chicago Cubs have the longest drought of a World Series title with 102 years since they last won in 1908, In fact, they also hold the longest drought without a World Series appearance, not having won the NL pennant since 1945. Even had they won the 1945 World Series, they would still hold the longest active World Series championship drought, the second longest being since 1948 by the Cleveland Indians.

There are several expansion teams that have never won a world series.