This is an article from the Nov. 14, 2016 issue
Longest Drought: KINGS (65 years)
Misery Index: CLIPPERS
What's worse: being terrible, being an embarrassment or being ignored? How about all three?
Longest Drought: MAPLE LEAFS (49 years)
Misery Index: MAPLE LEAFS
1917--67: 13 Stanley Cup titles. 1968--2016: Only 19 playoff series wins.
Longest Drought: RANGERS (56 years)
Misery Index: PIRATES
No titles or pennants in 37 years, 20 straight losing seasons (1993--2012) and then a competitive window that lasted just three years. Somewhere Francisco Cabrera is laughing.
Longest Drought: CARDINALS (69 years)
Misery Index: BILLS
Making four straight Super Bowls is good. Losing four straight Super Bowls is bad. Not making the playoffs this century is really bad.