I'm sorry that you are facing this. I think it is time for surgery, not bending back in place.
In the third photograph it appears that the keel
part that meets the rudder - the trailing edge of the keel
and the rudder foot - has separated from the keel as well as being damaged at the foot. I recommend that once you get the rudder loose you also remove this large part for repair or replacement.
Now you've got the rudder shaft, the rudder with a cut-off part of the shaft, and the keel edge/foot. Hmmm.
At the bottom of the rudder the shaft is not ticking out as far as it was when it was contained by the foot. That suggests that the shaft is no long bonded to the rudder. The shaft may have been pried out of the rudder like a nail out of wood. The foot is destroyed. The rest of the shaft is mangled.
Out of all that you might be able to salvage
the rudder. My bet is that the rest needs to be replaced, but there may not be a replacement out there for the trailing edge/boot. In that case you may need to fabricate a boot. I recommend that you consider a stainless steel
pipe with two welded-on flanges that can be through-bolted to the foot. That would be stronger than the apparently all-fiberglass original boot. It would also be removable for installing the rudder and a new shaft.
Good luck with it.