>>54223992020 is almost a cheating answer so leaving that out, 1993 and 1995 were awful. 1999, viewed with hindsight, was pretty bad too. 2009-2011 as a whole are really, really bad.
2009 is when all the guest GM stuff started. 2010 had a bunch of people leave or transition to part time, pushes for new/younger guys that didn't work out for various reasons from Del Rio to Sheamus to Kofi to the entire Nexus angle as well as ECW dying again. 2011 carried over much of the bad shit from 2010, including heel Michael Cole and the Anonymous Raw GM.
You had the Pipe Bomb and Summer of Punk angle but even that went nowhere with Punk basically playing second fiddle to everyone and his feud somehow morphing into a Triple H vs. Kevin Nash feud as well as garbage like the New Nexus and The Corre.