Drudge broke the monica lewinsky story, thats what really put him on the map. I have heard bits and pieces about what he makes, several years ago it was in the low million range. With the resurgence of online ad revenues that probably went up. His biggest plus is he only has one employee (last I heard.) Either way, he's doing well.
There is nothing wrong with having a shitty site when it delivers exactly what the audience wants. Just take a look at plentyoffish, or in a way even compare Google's front page to Yahoo. It makes graphic designers want to commit suicide.