I'm going to get a lot of shit for this, but please, hear me out for a minute.
Ron Paul, by using his government office and campaigns, got millions of people interested in libertarianism, and subsequently multiplied the number of voluntaryists. The reason he was able to have this effect was that the masses are deeply devout in the religion of statism, and on an emotional level, see anybody in federal office as an authority figure; a holy prophet. The people are automatically willing to listen, and entertain the ideas of, anybody in elected office. This is because their faith in the god democracy activates their trust in politicians and lowers their faith-defensive walls every time the politicians speak.
When some stranger starts preaching to a statist about government being unnecessary, the statist, as programmed, is inclined to immediately dismiss anything said, and become emotionally defensive of the almighty government. I engage and deprogram statists in-person on a regular basis, and probably about half of them plug their ears going "la-la-la roads roads roads", refusing to entertain the idea that roads would be of higher quality if they were competitive and funded voluntarily, such as by the businesses on the roads, driver subscription, or billboard advertisement.
If somebody the statist sees as government starts speaking about it, however, the statist's emotional defenses will be down, and they'll be able to be led to reason.
An elected official will have a much easier time deprogramming statists, than a non-governmental celebrity (a mere human). Politicians are classified under "authority" in the minds of the tax cattle. Woody Harrelson and J.R.R Tolkien are examples of anarchist celebrities, and they haven't drawn much global attention to the cause of liberty. They're not authority.
Besides, if there's anything anarchists are collectively good at, it's politics.
If just a few charismatic anarchists attained elected office, perhaps advanced to the level of federal office, or even a presidential campaign, it could create an enormous cultural shockwave and put anarchism in the center of the world's eye.
An anarchist that became a mayor, a governor, or a congressman, could gain a lot of media attention simply by doing and saying things that shock the tax cattle. When Ron Paul started preaching about the Federal Reserve, millions listened. Until then, no stranger would take you seriously if you spoke about debt slavery; they'd call you a tinfoil hat. Imagine if one of us became another Ron Paul, but talking about concepts like self-ownership, polycentric law based on property & consent, non-monopolized infrastructure, the non-aggression principle, taxation is theft, etc.
Imagine the hype it would draw if an anarchist governor announced his intention to secede his state from the US, then abolish the state government, and the private sector subsequently stepped in and started providing better alternatives to the wanted services the state currently provides. What if the infrastructure of New Hampshire, for instance, became completely privatized, and served as a working model of AnCapistan?
The most important part of an anarchist's vie for "high office", is to gain credibility in the eyes of the statists, such as by attaining local office or state office before going for the big federal spots. For this reason, Ron Paul influenced a hell of a lot more people with his run for President than Adam Kokesh is probably going to. The statists don't see Kokesh as authority, yet Ron Paul was. An anarchist could campaign on a platform of total drug freedom in Colorado, or unlimited gun rights in Texas. Pick whichever anti-state positions your voter base hold, and milk them.
Using the position of perceived authority to speak to the statists with the statists willing to actually listen, the elected anarchists could accelerate the conclusion of statism and usher in the end to humanity's government phase. Call it unprincipled, but this would just be using cultural engineering, by way of psychological manipulation, to change the world in the way it needs to be changed.