Richard M. Stallman, the pioneer of free and open source software, is the perfect subject for a biography. He is as intriguing as he is repulsive; as staunchly idealistic as he is constantly uncooperative.

I began reading Free as in Freedom, admittedly, because it is one of the few contemporary works available on Stanza (one of my top 5 iPhone apps), but a couple chapters in and I was hooked. Typically I’m not fond of biographers who play Freud, selecting key childhood events as catalysts that determine the rest of their subjects’ lives, but Sam Williams does an excellent job teasing out what Stallman himself tends to leave out of his own prolific writing: how his intensely inflexible personality has been instrumental in both his many achievements and his countless shortcomings.

Free as in Freedom is also a helpful introduction to the history of the open source software movement, and all the petty infighting that has led to its Balkanization fragmentation into this faction and that. But what stays with you is Williams’ often intimate portrayal of Stallman the man, a constantly angry, unhappy, and defensive man. His late nights writing code and studying intellectual property were propelled less by Stallman’s idealism and more by his anger at the fact that others weren’t as idealistic as he. Like so many leaders and great thinkers before him, Stallman was a great believer in humanism; and yet incapable of treating others humanely. (It seems that Stallman has no friends; only frenemies who begrudgingly admit their admiration for his idealism and intellect, but sigh and shudder at his micromanagement and stubbornness.)

Another point that stood out for me is just how behind the times Stallman has always been when it comes to the evolution of the computing industry; especially given how prescient his greatest achievement, the General Public License, was at the time. Stallman was still writing code for mainframe computers even when the personal computer revolution was well underway. He shrugged off the Linux kernel when he first heard about it and then spent much of the following decade taking credit for the eventual Linux operating system – which Stallman insists should be called GNU/Linux to reflect his and his team’s contribution.

Unfortunately the legacy of staying behind the times is still with the open source community today. As software moves unidirectionally from personal computer to the cloud (just as it once did from mainframe to personal computer), the open source community is still spending most of its time trying to get Audacity to crash less or Adium to finally incorporate video chat. If they don’t move to the cloud soon they will be left behind.

A couple weeks ago I was mentioning to a friend an article I read in the Times about Steve Jobs. Michael Maccoby, a psychoanalyst and self-described ‘expert on leadership’ described Jobs as fitting the archetype of the “productive narcissist“:

The very striking thing about productive narcissists, particularly men, is that they grow up in families where there is an absent or weak father figure. You can see this in narcissistic presidents like Obama, Clinton, Reagan and Nixon. They struggle with their identity and view of the world. So they tend to come up with a very original view of things and are then driven to find followers.

According to Maccoby, productive narcissists also tend to be anti-authoritarian. The description vaguely applied to both my friend and me. But it nails Stallman even more than Steve Jobs.

The problem with evaluating Stallman’s legacy – both as a hacker an as an intellectual – is that he has managed to piss off just about everyone and anyone who might have something nice to say about him. As Williams puts it:

Stallman the ideologue and Stallman the hacker genius, however leads a biographer to wonder: how will people view Stallman when Stallman’s own personality is no longer there to get in the way?

Williams’ own comparisons – Thoreau, Muir, William Jennings Bryan – seem unrealistically ambitious. But then that depends on how we finally decide to treat property in a century where atoms increasingly become bits. Already, Stallman’s writing on copyright and intellectual property has had profound influence on Lawrence Lessig and many other scholars who today are lumped into the “Creative Commons cartel.” In fact, earlier this year Lessig said this about Stallman:

I don’t have the courage of a Stallman. Too many of my cycles are focused on how or whether what I do will affect whether others like me. I am more comfortable on the inside than on the outside. And when we tried to find allies in this battle, I totally understood those who didn’t have the stomach for this. “Coward” is a name I’ve given myself more often than any other.

So, in the end, does Stallman have to be such an asshole so disagreeable to be such an idealistic force? Those who know him best say yes. Williams says yes. And, having read the book, I agree. Stallman is cursed and blessed with the gift of anger. It both drives him forward and drives others away. I have a hunch that, despite bouts of loneliness, he wouldn’t want it any other way.