Okay, care to elaborate more about what exactly are all the events, Kings, Men, guards etc. in such case? Then I could show you more clearly why it is wrong

But no, that was just a remark, it is simply not the right answer. Note at least one thing: if it was indeed Drengist, then if you look at the riddle, it actually says "my
mother" was born in twilight, and likewise it was
her path that ended by western shores, so - if it is Drengist that begins in Dor-Lómin and ends in the west, as you say, then Drengist would actually have to be the mother, and now the question is, who is the "child"? Because that is the answer we are looking for.
But anyway, I think you are somehow hovering around the right path to find the answer...