OS X and iOS are not free, and Apple led by Jobs changed the way that people thought about installing Applications on desktop operating systems as something that requires manufacturer approval (App Store), which led the way for others like Intel to make AppUp, etc. This restricts what the user has access to install is more of a setback for the free software movement than anything Microsoft ever did.
Jobs also changed the licensing program for Macintosh clones, making it too costly for the manufacturers to continue making machines. If there were Mac clones, then eventually perhaps freedom would have flourished.
Basically, Jobs was the ultimate technology monarchist and Stallman the ultimate technology anarchist. (I almost said capitalist and communist, but Stallman is all about free, not about centralized distribution and control.)
I'm not saying I agree with the man, but this is what he means by jail.