I wouldn't say the Raiders at all. Yeah they suck now, but they were a perenial playoff team a few years ago and have managed to be above average for most of their existence.
In the NFL its the Detroit Lions and its their own fault for not getting rid of Millen and trying someone else. They look like they'll be improving this year though, but I hear that every year.
In terms of management the Titans suck. They handled their cap situation horribly, lost everyone and then drafted Pacman Jones, all while still performing better than the Lions.
Baseball its the Kansas City Royals. Devil Rays get a pass as they actually acquire good young talent, they just don't have the money to pay them and they're in the AL East where the best they could ever hope for is a wild card spot and even that'll never happen.
Hockey its the Blackhawks and recently the Bruins.
Basketball its the Hawks and the T'Wolves IMO, they basically stopped attempting to build a team around KG a few years ago and have been relying completely on him to stay competitive.