The fundamental problem, in my opinion: as programmers, we hold rationality as a core value above most other things. We expect rationality from others, and we cope very badly with irrationality. To the extent programmers manage to understand irrationality at all, we have an almost moral inhibition against exploiting it. That makes us utterly awful at politics, which currently requires expert-level manipulative tactics to deal with the majority of voters, who don't deal with political and social issues in rational ways. Anyone who refuses to use such tactics will lose to those who do.
A political hacker would need to have expert-level skill in rhetoric, not just in rational argument and problem solving. This doesn't seem like an impossible goal, but we first have to understand and accept the fundamental problem, and get over the constraints we've hamstrung ourselves with.