Sméagol and the Gift
'Now!' said Sam. 'At last I can deal with you!' He leaped forward with drawn blade ready for battle. But Gollum did not spring. He fell flat upon the ground and whimpered.
'Don't kill us,' he wept. 'Don't hurt us with nassty cruel steel! Let us live, yes, live just a little longer. Lost lost! We're lost. And when Precious goes we'll die, yes, die into the dust.'
Devastated by this. Just a little longer, he begs. Even though his existence is a torment. Even though the will that holds him to life is barely his own anymore. He has long outlived his time but it's such a cruelty that now the only freedom for him is in death. I'm glad Sam didn't kill him but the whole scenario is awful.
When a mortal keeps a ring of power he does not gain more life, he continues, denied natural mortality as the fear of death is amplified and twisted into fear of separation, nothing matters anymore but the keeping, the continuing. In that miserable existence there is no peace, and at its end there is no graceful goodbye to life, there is only dust. Sudden, empty, and final.
It would take murder to spare him that. Or falling with the ring into the fire.
Bilbo let it go in time (did he feel anything when it was destroyed?) Frodo is freed of it now, though the toll it extracted for the separation was at very least a finger. It was too late for Gollum for the price to be anything other than it was, and that's brutal.
If you live long enough, death is no longer the enemy. What Sauron did to Gollum ensured that it would always be the enemy, to be feared and avoided for ever, once time and the ring had fashioned it into the only escape left. Evil.
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