Thinking of the Cowboys gets me thinking about some of the most painful fanbases in professional sports. They're perennial favorites in August and consistently crap the bed when it gets down to it. As a fan, I think it's worse to experience success and never succeed again than to never win anything at all. You can probably throw the Chiefs in there too, except expectations never seem to be that high I suppose. Who else belongs in this category? New York Knicks? Minnesota Twins?