Lively was an independent candidate for Governor of Massachusetts in the 2014 election. He ran again as a Republican candidate in the 2018 election. At the Massachusetts Republican Party's state convention on April 28, 2018, he received support from nearly a third of the delegates present, exceeding the minimum requirement to appear on the ballot for the primary election on September 4, challenging fellow GOP incumbent Charlie Baker. Lively lost the primary to Baker, with Lively receiving 36.1% support (98,214 out of 271,990 votes cast) and Baker the remaining 63.9%. In 1988, Lively began campaigning against abortion in Portland. In 1989, he joined Oregon Citizens Alliance and worked on the pro-life ballot measure for the 1990 general election. In 1991, Lively, together with Oregon Citizens Alliance, shifted focus from abortion to homosexuality citing the "rapid advance of that agenda in Oregon". In 1991, Lively assaulted Catherine Stauffer, throwing her against a wall and dragging her across the floor of a Portland church, at an Oregon Citizens Alliance event she had been trying to film. In 1992 he was found liable for damages in excess of $31,000. In 2006, Lively met with Latvian pastor Alexey Ledyaev to form an international anti-gay organization called Watchmen on the Walls, which the Southern Poverty Law Center has dubbed a hate group. Lively spent the summer of 2006 lecturing at Latvian universities and meeting with lawmakers, and preached at Ledyaev's New Generation church. During Lively's speaking engagements, he claimed that Western activists (backed by the European Union) were trying to infiltrate Latvian society and spread homosexuality, particularly to children. After his trip to Latvia, Lively then embarked on a 50-city tour of Russia and other former Soviet republics, sponsored by Ledyaev's church, which had roughly 200 congregations and a regional TV channel. As Lively traveled from the Baltics to Siberia, he pressed officials to outlaw the "public advocacy of homosexuality" and urged officials from passing anti-discrimination laws. Eight of the nine countries he visited eventually weighed nationwide bans on "homosexual propaganda," and five (including Russia) either have bills pending or have since passed them into law. Lively takes partial credit for this development and calls Russia's gay propaganda ban his "proudest accomplishment." On August 30, 2013, in response to anti-LGBT legislation in Russia, Lively wrote an open letter addressed to Vladimir Putin saying, "You have set an example of moral leadership that has shamed the governments of Western Europe and North America and inspired the peoples of the world."