Most counterproductive angles?

So as you know, WWE booking isn't exactly lighting up the logic meter these days; we have the heel champ making the valid points and the top babyface acting like the disrespectful punk, not to mention Sheamus pulling cheap shots to win and committing grand theft auto (Maffew summed it up best on Twitter: "WWE: Where faces are heels and heels are faces!"). That got me thinking about what would be some of the most counterproductive angles in recent memory, ones that made the good guy look like a dipshit, undermined a guy completely, etc, basically achieving the opposite of what the goal is. 
The first thing that jumps to mind is the Lance Storm/Stone Cold "Boring" angle. I understand the endgame there (repackaging Lance Storm into a goofy, cabbage-patching face, just give him some kind of persona), but having maybe the biggest 'face of all time bury Storm out of the gate with "BOOOORRRRRRRINNNNNG" chants (and as we learned with "What?", Stone Cold has a knack of getting the crowd to chant the simplest of words) that poor Lance would never live down was probably not the best way to do it. Why not have Bischoff, still effective as a heat magnet, berate Storm for killing his ratings every time he was on and THEN having Stone Cold light a fire under his ass? Instead, turning him into a jiving square (with a huge dick apparently) did nothing to change the fact that Storm was done once Stone Cold brought out a pillow and blanket to the stage.
What say you and the Commentators of Doom?

Oh, by far I'd say Kurt Angle getting his nuts cut off by HHH in 2000, where the finish of the angle was the exact opposite of what should have happened.  Angle should have stolen Stephanie and given HHH a reason to be jealous and pissed off, but instead Angle lost the girl and then ate a Pedigree.  It was mind-boggling.  Still is.  Same idea with the initial Randy Orton face turn in 2004, where Orton was made to look like a goof week after week and then lost the belt to HHH a month after winning it.  Took him years to fully recover from that.