Old Lion
Pay no attention to that man behind the curtain
LONGEST TITLE DROUGHTS, 4 MAJOR SPORTS:
Baseball -- Cleveland Indians (1948, 68 years)
Football -- Detroit Lions (1957, 59 years)
Basketball -- Sacramento Kings (1951, as Rochester Royals, 65 years)
Hockey -- Toronto Maple Leafs (1966-67, 49 years)
I guess one can make the case for the Kings franchise in basketball being worse than the Lions. Their 1951 title season was also the last season they made it to the final round/game of their sport. If you go by championships only, the Indians are worst, though they've played in 3 World Series since their last title.
Any team can lose 3 championship series. Getting there means nothing. Nobody counts second places in professional sports. Maybe it means something to win a conference to some, but that is just settling IMO.