Dirty Hipsters said:
Evangelion.
It started out alright, but the ending was just soo soo bad that it immediately moved the entire anime into the "worst show I've ever watched all the way through" category.
Apparently the movies fixed the ending of the series, but I couldn't be arsed to care at that point.
Welp.
The thing(s) you have to realize about evangellion's original series is that at the end the budget was low, they were getting criticized for the content of it, and most of the leads were becoming progressively more and more depressed to the extent that they had to be put on anti-depressants after they finished.
They were getting death threats over the ending for the series too.
Ultimately they just didn't get to deliver what they wanted to- the movies fix that. I'd also recommend watching the rebuild.
The thing about anime is that its never really a catastrophic failure- most anime has a manga as source material and they're usually picking what's already popular so its kind of like shooting fish in a barrel.
Still, if I had to say...
Worst communication for an anime:
Elfen Lied. Director completely disregarded everything pitched as satire on attempts at deep plot as.... deep plot. Fan-freaking-tastic. What results is an anime that's either extremely stupid or just incredibly hilarious if watched in the right way.
Worst timing to run out of cash:
(surprise) Evangelion. Anyone who's watched the last few episodes can tell you it's terrible. Set the premise for all future deconstruction animes that everyone must die. You're not just knocking over the dominoes you spent the last 18 episodes setting up, you're up-ending the table, driving a semi truck into the house, burning the place down and then nuking the town from high orbit.
Worst
Communicated anime:
Foolie Coolie. Don't get me wrong, it's a great show. The only problem is that they were trying to be silly and seemed to have accidentally made one of the deepest anime, ever, and did it in less than 10 episodes. There's 100+ episode series that fail at that same attempt.