Is the frequency with which Lannisport sacked by Ironborn at all believable or is it a simple case of Martin hand-waving the second richest city in Westeros into a incompetent Ironborn punching bag. If you combine the City Watch (reputedly an excellent force) with the obvious militia formed from within the guilds of such a prosperous city (as you pointed out happened in real life history), shouldn’t it be impossible for reavers to simply steamroll Lannisport’s defences time and again?

It happened once with the Red Kraken, when the Dance had left Lannisport “thinly defended,” and that expedition was repaid in full by Joanna Lannister and Ser Leo Costayne. 

It was raided a second time during the Greyjoy Rebellion, but there’s no evidence that the Greyjoys went further than burning the fleet in the harbor. 

But that’s it as far as mentions go in the WOIAF. So twice in thousands of years doesn’t sound too bad. 

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