I'm honestly not sure how I feel about his argument that the GPL is no longer needed. While I'm more sympathetic with BSD licensing now than I was 10 years ago, I do think that the GPL still makes a lot of sense for infrastructure-type projects.
My gut feeling is that his position that the existence of the internet makes concerns about the whims of any given legal jurisdiction irrelevant is more than a bit naive.
I think his problem with the GPL is that it allows "open source" project owners to constructively restrict commercial use (by offering a separatel-licensed (non-GPL) version.)
I also openly question the truth of his statement that he was an early reader of the JVM specification.
I assume you watched the video? (I recorded and posted it) Personally, I actually thought he was pretty modest overall. He did mention his academic background and 'hacker credentials' when he was discussing functional programming languages and Haskell in particular, but other than that I didn't think he came across like he was promoting himself. I've been running this users' group for 12 years and I've seen much bigger egos from people who didn't have ESR's credentials.
My gut feeling is that his position that the existence of the internet makes concerns about the whims of any given legal jurisdiction irrelevant is more than a bit naive.