Eldest?

[narfforc]

In HoME Vol12 The Peoples of Middle-Earth under Last Writings is a section about Cirdan. It states thus;

Cirdan was a Telerin Elf, one of the highest of those who were not transported to Valinor but became known as the Sindar, the Grey-elves, he was akin to Olwe, one of the two kings of the Teleri, and lord of those who departed over the Great Sea. He was thus also akin to Elwe, Olwe's elder brother, acknowledged as high-king of all Teleri in Beleriand.

It also states that Cirdan was the leader of those who sought longest for the lost Elwe.

Although Cirdan is very old, I do not think he is as old as Tom, for he came First and Alone to Middle-earth. The Istari are older, yet Gandalf cannot say so, for that would spoil the illusion of them being just old men (this may have already been sussed, as they had been drawing their pensions for some time). My vote goes with Tom as Eldest, purely because it is he who calls himself so, and who else can say they saw the first raindrop or the first acorn; and who can say he was there before The Dark Lord came.