In 2011, he participated in the Occupy Boston protests. He is the subject of the 2014 documentary, Who Is Vermin Supreme? An Outsider Odyssey, which follows his 2012 campaign and explores his life as an activist and political prankster.
Supreme discussed his political views in a 2008 promotional video. He stated he was registered as a Republican at that time, but that he leaned toward anarchism. He asserted that libertarians "are just about abolishing the government and letting shit fall where it may," which he called a mistake; he also asserted that Republicans want to nullify the government, but "offer no alternative to helping people other than charity." Supreme's vision of anarchism holds no need for government, but depends on citizens to take responsibility for themselves and for others, citing "mutual aid and support and care to our fellow citizens" as key elements. To that end, Supreme called for a gradual dismantling of the government, while citizens take up the slack. He asserted that Americans no longer know how to be citizens, placing some of the blame on schools that teach in "very twisted and jingoistic fashion".
In the video, Supreme discussed his presidential campaign. He describes his "joke humor" campaign as a response to the lies people are fed by the media and by the government.
August 25, 2012: Supreme announced his new political party, the Free Pony Party, and that he has chosen fellow fringe opponent Jimmy McMillan as his running mate. Conversely, McMillan stated he was still running for president on his own Rent Is Too Damn High platform, and that Supreme would be McMillan's running mate.
October 5, 2012: He participated in a debate hosted by Peter Schiff in the Peter Schiff Radio Show, which featured a panel of overlooked presidential candidates including Jimmy McMillan on the Rent Is Too Damn High Party ticket; Santa Claus, independent write-in candidate, and Edgar Lawson, write-in Republican presidential candidate.
Supreme attempted another presidential run in 2016. He embarked on a tour of 20 cities to build support for his campaign and sought to qualify for matching funds from the Federal Election Commission (FEC). He filed as a candidate in the New Hampshire Democratic presidential primary on November 21, 2015, and received 259 votes in the primary on February 9, 2016, coming in fourth after Martin O'Malley. He was, however, not invited to return to the Lesser-Known Democratic Candidates Presidential Forum, due in part to him glitterbombing Randall Terry at the event in 2011. Shortly before the primary, he was observed questioning Republican candidates Chris Christie and Ted Cruz through a bullhorn. On March 4, 2016, he switched his affiliation to the Libertarian Party, claiming his rightful position as Sage and Oracle for Libertarians throughout America, and possibly Belize as well. He received the vote of a single delegate in the first round of presidential nomination voting at the 2016 Libertarian National Convention.
Supreme co-wrote and stars in the 2009 film Vote Jesus: The Chronicles of Ken Stevenson, in which he poses as a right-wing political candidate to gain access into the world of American fundamentalism.
In 2012, Supreme starred in a web series entitled Learnin' with Vermin that uses a fictional version of his presidential campaign as a platform to teach political concepts such as voting methods.