I've been using GWT solidly for the past two years (not my choice for the project, but sometimes you just have to play the hand you are dealt) - and IMO GWT's biggest problem isn't so much that it is Java, but rather that it is Java without any dynamic features (i.e reflection, late binding etc.)
I could rant at length about the dark alleys that GWT's overemphasis on static analysis can take you, just a massive hairball of impenetrable compile-time code generation in order to provide features that would be trivial if you could just reflect on things. Ironic, given the fact that your code is actually running in Javascript.
So while I don't believe static typing is inherently a bad thing, you can definitely have too much.
My IDE (phpStorm) helps quite a bit with this, currently - provided I document everything well - but I wouldn't mind having a compiler to smack me in the face when things are wrong.
I would say ActionScript, but FalconJS hasn't been released yet. There are other projects (such as roy) that are more functional in nature as well.
I was a flash developer way back (2003), I hear you.