A Question of Loyalty

[Gordis]

"Old times" in the quote provided by Hakon may indeed refer to times before TA 2942, before Sauron had returned to Mordor.

But "the bad old times of the Great Siege" referred to in the following quote almost certainly happened at the very end of the Second Age:

Gorbag: `You may well put your thinking cap on, if you've got one. It's no laughing matter. No one, no one has ever stuck a pin in Shelob before, as you should know well enough. There's no grief in that; but think-there's someone loose hereabouts as is more dangerous than any other damned rebel that ever walked since the bad old times, since the Great Siege. Something has slipped.'

I wonder could ol' Gorbag be 3000+ years old?