Did Gollum deserve death?

[Raynor]

If he was simply 'wicked & damnable' why would he inspire pity?

Because they saw he has the choice to repent; Tolkien stated that nothing is wholly evil, since it would be absolute zero. The same would apply to Gollum. Also, Tolkien stated that one must show pity even when doing so may seem disadvantageous; true pity is present when it is contrary to prudence.

It seems to me you are taking a 'Balrog's Wings' approach here - Tolkien uses the word 'wings' & you take it literally.

Was that an attempt to somehow demean my argument? Because the barlog wings debate is no settled, unless you consider your word the ultimate authority . While Tolkien may have acknowledged Gollum's problems, he still considers him as such, and I don't see how either of the three labels can be taken figuratively. Surely, you are allowed to do so, if you want.