Could you please provide some proof that he used to mod r/jailbait?

According to the AMA where a loud of this came up, from what I understand, in the early (super early) days of Reddit, you used to be able to appoint people as mods if you had X amount of karma (I think it was 100k). I can't find that comment thread now fully explaining it, but I wouldn't be surprised if it was removed. But the gist of it is someone appointed him a mod there and it didn't last long. So mostly true, but he didn't set out to be a mod of his own free will.

That's what I've been told as well. I think that's why there needs to be approval to appoint mods as well. I think the bigger issue is why reddit let that sub remain for as long as it did. It had to be covered by the media for it to be banned (iirc. or was that a different sub?).

Back then they used the term bastion of free speech and wanted to stay true to that, despite not wanting that sub, it was only a matter of time before they grew large enough that they had to drop the philosophy for the benefit of PR and advertising.

As I recall, there was an uproar back then as well when they started cleaning up subreddits. (/r/jailbait was one, /r/beatingwomen another, and a bunch of other subreddits about various illegal activities.)

In fact the vitrol directed at spez currently really reminds me of that, there were pictures of the then-CEO's face everywhere along with "fuck Ellen Pao". Then, funnily enough, spez came in (came back) as the replacement and people were happy again because he was one of the OG admins.