Why is this man smiling?

He is smiling because he is winning. His vision for free software is taking serious hold. It is possible to live a productive digital life using only free software, and I pretty much do (damned "free" Flash player).

When he wrote "the prospect of charging money for software was a crime against humanity" at first I thought it was just baseless, humourous hyperbole, but upon reflection I came up with a different perspective on it. Software allows for automation. Human effort is expended to create software to solve a particular problem, and the human is compensated for that. But should the method for achieving that result become "property"? And whose "property" will it be? Almost certainly, that "property" will belong to a corporation. And corporations are not human. They are legal "people" (emancipated by the U.S. Supreme Court) but they are immortal, amoral, and their true role in our society is incompletely understood. Without the mechanisms provided through free software, and because of the structure of copyright (dictated by corporations), that "property" will almost certainly not be made available to anyone but other corporations able to pay for it. Being immortal, they enjoy many advantages humans do not, and humans cannot reasonably compete in certain areas.

Stallman is a clever guy. He figured out how to do a jiu-jitsu move on copyright to give people an economic model to put software in the hands of other people and organizations (yes, even other corporations). He invented copyleft, a way of enforcing the continued sharing of software, and did it in such a way that corporations couldn't cut it down without sawing off their own arms: copyleft is based on copyright. Without his invention, there would be no practical alternatives to corporate tools made by corporate tools.