You have to remember that Stallman was around before Jobs' day -- he was performing real work at MIT when Apple was initially conceptualized. Stallman therefore is apparently less vulnerable to the reality distortion field and does not unduly offer oblations to a guy who was obsessed with shininess at the expense of hacker culture. Jobs went to lengths on many products to prevent tinkering in an age when computing was still very open and very academic, because Jobs didn't want any little peons messing up his perfect devices. Hence Stallman's quip that Jobs made computers as a jail cool.
If you think about this statement from Stallman's perspective it really makes a lot of sense, and I think it is ridiculous that the Steve Jobs hero worship pervades so deeply as to not recognize that Jobs was a control freak even after Apple products were sold and in the possession of customers, and that some people, particular contemporaries of Stallman's stripe, may not have been fond of that. I doubt that the release of the iPhone really did much to persuade that set of people.