Never. It would be like working for a big company, but more so.
* "PG - He's for me!"
* "Paul Graham - He's the man!" [sic]
* "No more DC slackers, we want YC hackers!"
* "Paul Graham: Invest in America"
* "PG: Bringing the 'start' back to Capitol Hill!"
Related note: I'm available for campaign management jobs. :)
Getting elected in the first place is more painful, though.
Now a Programmer Party would be a wonderful idea, at least in theory. It could run on an agenda of tidying up the laws and making them readable and responsive to people's needs. On the other hand, you only have to look at political arguments here on HN to realize that programmers are as ideologically fractured as any other social group. As soon as a question of economics or the scope of government power arose, a schism would occur.
Clearly what we need is to declare a Politician class, and then create multiple objects derived from that class, taking full advantage of inheritance, polymorphism and operator overloading. This will solve all our problems, just as soon as we agree on which compiler to use...
Plus, something tells me Paul can raise enough money to win in a few minutes.
Many countries run parliamentary systems with party lists, such that candidates for office may be experts on a narrow range of issues rather than needing to appeal to a particular geographical constituency, but the US system is structured against that.
On a related note, it is interesting for those of us in California to watch how the candidacies of Carly Fiorina and Meg Whitman are playing out.
Could PG say "what you can't say" if running (or holding) office?