Losers

I looked up what teams had the longest losing streaks in professional sports, to see if the Cleveland Cavaliers will be able to break them, and happened to come across the longest losing streak I had ever heard of, Cal Tech lost 207 straight games in Division III men's basketball.  Here's a list of ten long streaks, including a boxer who lost 88 straight bouts (not me, I retired after 5).  But here's a story putting forth the Washington Generals as the losingest team, and it starts with a Simpsons quote:

Krusty's accountant: "Let me get this straight. You took all the money you made franchising your name and bet it AGAINST the Harlem Globetrotters?"

Krusty the Clown: [miserable] "Oh, I thought the Generals were due!"

Note: The Cavs last won on December 16.