Gildor's got a gun

[Eönwë]

Originally Posted by alatar

Okay, just so we're not limiting the discussion, we don't have to consider only the Nazgul or the Third Age. Was there ever an event where the 'good' side decided to put a hit (successful or not) on someone on the other side (human royal affairs not withstanding)?

Well, since LOTR and in fact, the entire legendarium is based on what people knew, it could be that there were a few low-profile attacks that were just counted as "mysterious disappearances in the hands of the enemy" or something. There wouldn't be any survivors on the "good" side to record the events. We only hear of Fingolfin because of the special circumstances.

Originally Posted by alatar

Gandalf was able to infiltrate Dol Guldur - twice, I think. Couldn't someone have done the same and taken out 'someone?!?'

I don't think so. Gandalf's mission relied on stealth. If someone was found dead he would hhave had to deal with the entirety of Dol Guldur (I assume it was reasonably well-armed as a fortress), which is no mean feat, even for a Maia (especially one in a limited form).