Obi-Wan never understood Icarus.
But a small, roughly shoved aside part of him hoped that Luke could. And even as he explained that Anakin was now more machine than man that part of him looked into Luke's darkened eyes (surely that was a trick of the light) and dreamed.
A drown man could not be brought back to life of course and once someone went over to the Dark Side, forever it would dominate their destiny. Salvation for one suffering either fate was impossible.
Still…
Maybe, just maybe Luke understood Icarus,
And could take him from the sea.