What's Oldtown's relationship with the rest of Westeros?

whitewolfstark, I think that you just might be into something. Oldtown and the Hightowers seem to have been afforded more respect throughout history than the usual vassal houses. And Martin has been inspired by the history of what is now Great Britain. Do you know about any specific events surrounding the history of the City of London? Seems like it might be something interesting to investigate. Nice catch!

I think it's likely that the Hightowers and other powerful people of Oldtown are bitter about the fact the Targaryen dynasty usurped their position as Westeros' dominant port and seat of political and clerical power.

Fortunately, Oldtown and the Hightowers still hold the Citadel and its vital communication network under their sway. Thus, over the last few centuries, the maesters have become the primary tool for Oldtown to re-establish its once preeminent political and economic clout among Westerosi cities. This motive works especially if Oldtown's origins lie with a people who come from one of the older, highly advanced Essosi cultures, who preferred to consolidate their power under large city-states.