Monkeysphere aims at adding a web of trust to the SSL certificates system, but the CA chain problem seems to persist (although I must admit I'm not up to speed with the actual details).Since i'm one of the Monkeysphere developers, i figure i should respond!
Let me clarify that Monkeysphere doesn't just work in places where X.509 (the SSL certificate system) works. It works in other places too (like SSH connections). And I don't think that the CA chain problem that remains in Monkeysphere is anything like the dangerous mess that common X.509 usage has given us. I do think that at some level, people need to think about who is introducing them to other people -- visual or human-comprehensible representations of public key material are notoriously difficult to make unspoofable.
On the subject of distributed naming: OpenPGP already allows distributed naming: every participant in the WoT is allowed to assert that any given key maps to any given identity. Duplicates and disagreements can exist just fine. How an entity decides to certify another entity's ID without a consensus global namespace is a tough one, though. If i've always been known as "John Smith" to my friends, and someone else has also been known as "John Smith" to his friends, our friends aren't actually disagreeing or in conflict -- it's just that neither of us has a unique name. The trouble comes when someone new wants to find "John Smith" -- which of us should they treat as the "correct" one?
I think the right answer probably has to do with who they're actually looking for, which has to do with why they're looking for someone named "John Smith". If they're looking for John Smith because the word on the street is that John Smith is a good knitter and they need a pair of socks, they can just examine what information we each publish about ourselves, and decide on a sock-by-sock basis which of us best suits their needs.
But if they're looking for "John Smith" because their cousin said "hey, i know this guy John Smith. I think you would like to argue politics over a beer with him", then what matters is the introduction. And OpenPGP handles that just fine -- if their cousin has only ever met a single John Smith, that's the right one. If their cousin has met several John Smiths, then the searcher would do well to ask their cousin some variant of "hey, do you mean John Smith or John Smith ", or even "do you mean the John Smith who Molly has met, or the one who Charles has met?" (assuming that Molly and Charles have each only certified one John Smith in common with the cousin, and not the same one as each other), or to get a real-time introduction to a particular John Smith, where his specific key is somehow recordable by the searcher for future conversations (or beer drinking). This is what we do in the real world anyway. We currently lack good UIs for doing this over the network, but the certification infrastructure is in place already.
What we're lacking in infrastructure, though, is a way to have a distributed addressing. Roland's proposal was to publish addresses corresponding to cryptographic identities within some DNS zone, or in freenet or gnutella. Another approach (piggybacking on existing infrastructure) would be to include IP address information in the OpenPGP self-certification, so the holder of the name could claim exactly their own IP address. This could be distributed through the keyserver network, just like other updates are today, and it could be done simply and immediately with a well-defined OpenPGP notation. I'd be happy to talk to interested people about how to specify such a notation, and what possible corner cases we might run into. Drop a note here, or mail the Monkeysphere mailing list or hop onto #monkeysphere on irc.oftc.net