I think his dust up with Google re HTTPS rubbed a bunch of people the wrong way. On one level, he's of an age where good intent was assumed on the web, so security wasn't a big concern.

(On that note, ask John Siracusa how it felt to have TTYs @ BU be "world-writable" in 1993)

On the other hand, that world is largely gone and the web is much more fraught with peril these days.