From that position I was able to observe fairly closely how the GNU project was being led, technically, in the days before the Linux kernel had had any real impact.
RMS's technical leadership was, I think, not very skilled. Let me explain what I mean:
If you were working on a program and sought his advice, he was very good at zeroing in on the issues and giving excellent advice. And sometimes if you were working on a program and he noticed something he didn't like about your approach, his criticisms were very good. People used to tell stories about how good a programmer he was and those stories were basically all true. He was sharp and I assume that, in spite of his age, he still is.
The problem was that he showed no effective capacity to really lead the larger meta project of pulling together a complete OS. He tried -- with projects like autoconf and documents like the GNU coding standards. And he kept a list of programs that, once we had those (he reckoned) along with a kernel -- GNU would be "done". That was about the extent of his "big picture" for project management.
Mainly, he concentrated on advocating for the idea of software freedom. I think the gambit was that if enough people demand their freedom, the project of organizing a GNU project would become easier. I don't think this gambit worked.
That was never a clear enough, coherent enough, or informed enough vision of the complete GNU project and, consequently, GNU has never really successfully gelled. You can grab some "100% libre" distributions, these days, but only barely. There is no sustainable culture and technical organization there ("yet", I hope).
The RMS failure I see is a failure at being a community organizer of GNU programmers. A lot of people got the vague idea of a GNU project. Many of us were happily recruited to the goal. But everyone I worked with at the FSF, including me, kind of went off in various incoherent directions -- doing what we guessed would help and that seemed interesting to us. We never "pulled together as a team" and, in the GNU project, that still doesn't happen.
The GNU project gradually accumulated a heck of a lot of very good "parts" but could never gel. The first three world-changing releases (GDB, GCC, and Emacs) really startled people. The various shell/text utilities in those early days spread because they were often usefully a little bit better than the proprietary "native" equivalents shipped by Sun, Dec, AT&T, etc. People sat up and took notice but behind the scenes the project of setting up a lasting "complete OS" project that would promote software freedom for all users ... never quite came together.
The "open source" people -- who I also later worked for, because I made a mistake in trusting them at their personal word to me -- seemed at first like they might help bring resources to the problem. In fact, what they mostly concentrated on was creating proprietary products using the free software "parts" from the incomplete GNU project. In the early days they sought to monopolize some of the key labor for the GNU project (and they succeeded, because they paid much better than RMS and many of those particular hackers didn't really give a shit about the freedom of users). As the "open source" industry matured it perfected its model of a perpetually incomplete / inadequate free software OS as a source of inspiration to enthusiastic youngsters, realized in practioce as a perpetually freedom-denying set of proprietary OS products. Companies like Red Hat and Canonical realized that they could exploit the deficit of community organizing to charge high rents for libre software, so long as they don't care seriously about the freedom of users. That's what they did and what they do.
So in my view, RMS was not good (and still is not good) at leading the GNU project -- but the real tragedy is brought on by the glad-handing, deep-pocketed, "open source" rentiers who place concern for their own profit above the freedom of the community.
Debian is a 100% free distribution, with a strong culture and high technical organization. It was the GNU distribution in the 90's until they parted ways.
Are there not dozens if not hundreds of distributions of free software based on Linux and the GNU core? Compared to the early days of Linux (and GNU as well), I'd say Free Software as a whole is doing pretty good. The very existence of those distributions and the amount of software based upon them is your sustainable culture and technical organization. Canonical and Red Hat could go away tomorrow and they'd still be there.
And now we get to the real heart of the matter. Is it about giving companies, users, and communities the freedom to do what they want to do? Even if that thing is proprietary software, or open core models, or sharks with laser on their heads? Or is it about political, social, and technological control? The Apache foundation is about the former, and so is the Linux kernel. But the FSF has always been about the latter. It looks like they have poisoned your thinking too.
The world is not so simple that either you have total freedom to do anything, or you have complete locked down control of everything. Some freedom is about maintaining others freedom with the use of restrictions. The most common ones are "you must not kill, you must not steal". Those two are social control, but with the goal and effect of more freedom. That's not poison that kills life, rather that is protection preserving life.
Having products, be that a phone, a book reader, or a browser that users buy, this same users will think that they are the owner of it and thus in control. If then by technical means someone else actually has the complete control over the thing, that it is at least morally wrong, if not something that should simply be illegal.
To take an example, if my browser suddenly got infected with spyware and disabled ad-block, I would get angry and consider that the people behind said spyware should go to jail. If my browser suddenly got pushed with a remote update which by it's developer decision permanent disabled ad-block, I should be completely accepting of it? If Firefox did this, they would get forked as by MPL. If Firefox was proprietary software, no such thing could happen.
A foundation that say clear No to giving the developer control as if they had property owership of my phone, my book reader, my browser, is not a foundation about political, social, and technological control. Its about ensuring political, social, and technological freedom by restricting behavior that would normally be considered illegal and immoral if done outside the domain of IT.
Seriously? He's not 100, you know. Why wouldn't he be as sharp, or sharper, than ever?
Anyways, I do agree that Debian should be the distribution the FSF should support instead of gNewSense.
This is why most people think he's a fucking crackpot.
I think it is certainly an arguable question for the Free software/GNU community although I expect most could agree that they are bet positive for Linux and open source in general.
Given suitable hardware that doesn't need firmware blobs, distros like Fedora are 100% free software. Red Hat Enterprise Linux is also 100% free - you can download all the source from ftp.redhat.com and check that yourself.