In the 2000 U.S. presidential election, Weigel voted for Ralph Nader, and served as a Delaware college elector for Nader.[18] In the 2004 election, Weigel voted for John Kerry. Weigel later wrote that "[he regrets] the Nader vote, but not the Kerry vote, as a weak Democratic president with a conservative Congress would have been pretty tolerable in retrospect".[18] He voted for Jack Ryan in the Illinois United States Senate election, 2004 Republican primary.[19]
Since early 2007, Weigel has been a registered Republican in the Washington, D.C. area,[20][21][22] in order to vote for Ron Paul at the Republican primary stage of the 2008 presidential election.[23] In 2008, Weigel voted for Barack Obama, explaining "I really don't think McCain has the temperament to be President or the interest in standing up to a Democratic Congress... I've got the luxury of a guilt-free, zero-impact vote in the District of Columbia, which I would cast for Bob Barr if he was on the ballot".[18]
In January 2011, Weigel stated that he has voted for Republican Patrick Mara on elections to the Council of the District of Columbia, and that he has voted for Mara "every time he's been on the ballot".[24] He confirmed this in April 2011.[25]
In the Republican Party presidential primaries 2012, Weigel voted for Jon Huntsman, despite him having withdrawn from the race, because "If you looked past his whiff of a tax plan (Huntsman recommended using the flat rates that Simpson and Bowles recommended not using), the guy had a few good ideas."[26] In the 2012 general election, Weigel voted for Gary Johnson.[27]