Feels kind of evil and orwellian. rms (without the premeditated scheming) does something similar but blunt and people resist. We intuitively feel that if you make us use your words, you get power over us.
The truth is 'hack' as a phrase is becoming overly used, and taking value away from the actual terminology he is trying to advocate, a terminology that is associated to cleverness.
Not everything can be clever. At some point the usage of the phrase turns into marketing hype as a way for someone to gain the attention of a particuliar group.
"A xxx for hackers' "how I hacked xxx"
It's really just a way to grab people who self identify with that word, they don't really mean those pitch lines. It's not FOR hackers, it's TARGETTED at "hackers".
Not every single accomplishment of rms' is a hack. That ambiguity is exactly what is killing the value of that word. Not every action of a hacker is a hack, nor are all the solutions they seek 'hacks.'.
I think he chooses not to change his way of presenting it because he's presenting a philosophy, rather than simply trying to convince people to agree with him. I used to think he was a nut, the more time that passes, the more I realize just how perceptive and correct RMS has been about a great many things...
I guess this doesn't quite qualify and he may not even be the originator of the idea, but I thought it was pretty clever:
http://www.wired.com/opinion/2012/11/richard-stallman-softwa...
I think he probably has some personal moral code that prohibits him from trying to hack systems above a certain level of abstraction. Computers and security policies are below it, people's minds, emotions, and opinions are out of reach. In other words, the art of marketing is completely outside it.
YC on the other hand has a much higher bar for what is hackable, including things like getting user growth through clever marketing and viral loops, and keeping your startup solvent by selling breakfast cereal. RMS wouldn't go near these types of things, but they are in line with the hacking ethos.