And then you have the Toronto Maple Leafs that last won it in 1967. A little under a 60-year wait.
The longest droughts in the NHL are:
1967-Toronto Maple Leafs (last Cup before modern expansion)
1970-Buffalo Sabres (finals series appearances in 1975 & 1999)
1970-Vancouver Canucks (finals series appearances in 1982,
1994, and 2011).
1975-Philadelphia Flyers (also appeared in 1976, 1980, 1985,
1987, 1997, & 2010 finals).
1979-Winnipeg Jets/Phoenix Coyotes/Utah Hockey Club (has not appeared beyond 2nd round of NHL playoffs).
NBA—1951-Rochester/Cincinnati Royals/Kansas City/Sacramento Kings
1958-St. Louis/Atlanta Hawks
1968-Phoenix Suns (has never won a championship)
1970-Buffalo Braves/San Diego/Los Angeles Clippers (has never won a championship)_