5. Team Rocket
So Team Rocket is only right above Team Skull on the list because their plans never amount to more than trying to make a quick buck despite being significantly more competent.
Featured in both Kanto and Johto, Team Rocket has probably the most half-baked ideas in all of the series.
Selling fossils in Mt. Moon, and overpricing Slowpoke tails in the small Azalea Town sum up some of their more ambitious plans.
Sure, they run experiments on a Magikarp to unnaturally evolve it into a red Gyrados, but what does that get them? Some shiny Pokemon? We have plenty of those.
Also, we defeat Giovanni, the leader of Team Rocket, and he just gives up. We even time travel to the future with the help of Celebi and beat him again, leaving him in a cave to live out the rest of his days like the real loser he is.