I am a baseball fan first, so I will address that first:
If you listen to Cincinnati Reds fans, they will say the Reds. Last playoff, 1995. Last winning season, 2000. Last trophy: 1990.
You also have Baltimore, who have not had a winning season since 1997 - which was also their last playoff appearance. Last trophy: 1983.
The Texas Rangers might qualify: Since the franchise started in Washington in 1961, they have been in the playoffs a grand total of three times...all within a 4 year period. But, they have had too many winning years recently (including this one) to be included. They do have the third worst winning percentage of active franchises, though at .470.
Yes, the Rays were in the Series last year - but they still have the worst winning percentage of all active teams at a remarkable .425.
The second worse winning percentage for active franchises? The San Diego Padres (.462). But, the Padres have too many good years in there.
(By the way...tied for fourth are the Mariners and Phillies. The top three are, of course, the Yankees, Giants and Dodgers, respectively).
That leads us to the bottom three.
The Royals. Last playoff and Championship year were in 1985. One winning year since 1994. They have lost 100 games in three of those years since then.
The Pirates. Last playoff was in 1992. 1979 was their last Championship season. But only one 100-loss season in the last 20 years...and two since 1954.
The Nationals. In their 40-year history, they have had one playoff appearance. One. They, of course, lost. Their lifetime .476 percentage really isn't horrible (better than the Orioles, actually). And they have had only 3 seasons which they lost 100 games.
However, I really dislike former Nats GM Jim Bowden. So, my nod goes to them.
(oh, yeah...the Cubs. They have had too much recent success to qualify. Yes, there is that 100 years without a championship thing...but still, they always at least seem to have a chance. Teams like the Reds, Royals, Ranger, Pirates and Nationals seem to have no chance every year recently).
As for football:
Gotta be my Cincinatah Bengals. In baseball the deck is stacked against teams like the Pirates. Small market teams have almost no chance.
In the NFL the league is built on parity. There is a solid salary cap and TV revenue sharing. There is no excuse for a team to never be good.
Yeah, that is mine, as well. It amazes me how one of the brightest minds in sports history (Paul Brown) is even distantly related to the clown who owns the teams now. I keep saying that the only way the franchise will ever become a consistent contender is to get rid of him...but he will never step down.