Here is my top 5:
1. Oakland Raiders -> an absolute train-wreck of a franchise. Al Davis still believes it's 1975. No clue what he is doing.
2. Pittsburgh Pirates -> Pirates plan: Find a good prospect. Bring him up to the big leagues. Develop him. And trade him to a contender before he reaches his prime for more good prospects, then repeat.
3. LA Clippers -> Bad management with a team that absolutely nobody cares about. Never will succeed with the Lakers in the same town.
4. New York Knickerbockers -> They just aren't sure what style of basketball they want. They will be off of this list if they sign Lebron.
5. Phoenix Coyotes -> Terrible idea by the NHL to put a franchise in the desert. Bad team with bad attendance. They won't be in Phoenix much longer.
Honorable Mention:
Washington Nationals -> Nice new stadium. Bad team with little hope but have some nice prospects in their farm system.
Detroit Lions -> They would be on the list but since they have fired their GM they seem to have a plan and hope for the future.
Minnesota Timberwolves -> Had some nice teams in the late 90's and early 00's but never did much with the likes of Garnett and Co. They have been dreadful ever since. Some good young talent though which provides a glimmer of hope.
Cleveland Indians -> This might surprise you but next to the Cubs they hold the longest drought without a World Series title. That's not why I chose them though. Indians fans haven't been happy with the team since they allowed several players to leave in recent years for basically nothing in return. CC Sabathia, Cliff Lee, Victor Martinez, Jim Thome, Brandon Phillips, Ryan Garko, Franklin Gutierrez and Coco Crisp. They have really fallen the last two years in the AL Central.
Chicago Cubs -> When you can't win a championship in over a century you're not doing much right. Management has fallen behind on Wrigley Field upkeep in recent years as well.
New York Islanders -> Basically have been irrelevant since the early 90's. A few playoff appearances scattered since keep them out of the top 5.