Prior to 2016 Kessler was virtually unknown. In November of that year, he revealed lewd and offensive tweets made by Charlottesville vice-mayor and councilman Wes Bellamy. Bellamy, who is also a teacher at Charlottesville’s Albemarle High School, first drew criticism from Kessler when he called a press conference to call for the removal of the Robert E. Lee statue in Charlottesville in March 2016. In December, Kessler began circulating a petition demanding that Bellamy resign or be removed from office. In January 2017, while attempting to gain signatures for his petition Kessler was arrested for misdemeanor assault. He pleaded guilty and was sentenced to 50 hours of community service.

Kessler was also convicted for shoplifting, obstructing justice, and failure to appear, in addition to numerous traffic citations. Many on white nationalist forums have questioned his background as it seems he was involved with the Occupy Wall Street movement and previously supported President Barack Obama. People who know Kessler have confirmed that he previously voted for Democrats and was involved with the Occupy movement in Charlottesville.
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Kessler was one of the organizers of the Unite the Right rally on August 12, 2017. The rally was a protest of the removal of the statue of Robert E. Lee, a cause Kessler had taken up a year earlier when began his crusade against Bellamy. Kessler was also involved in a smaller protest of the removal of the statue on May 14, 2017 which ended in a torch lit march. At this event he was arrested for failure to obey an officer's commands.
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In March 2016, Bellamy called a press conference to call for the removal of a statue of Robert E. Lee from Emancipation Park. This drew the criticism of activist Jason Kessler.

In November of that year, Kessler revealed a series of lewd and offensive tweets made by Bellamy in the past. In the tweets Bellamy stated that he hates black people who "act white" and "talk white" and considers white women to be the "devil." In another tweet he said hates seeing "White people in Orangeburg." Other tweets included the homophobic slur "faggot" and sexist remarks such as “I’m all for equal opportunity..but a Female Principal with a school full of female teachers is fkn a sure fire way to fk our lil boys up smh,”

Bellamy apologized for the tweets and resigned from both the Virginia Board of Education and his teaching position. However, he did not step down from his position as vice-mayor. In December, Kessler who labeled Bellamy as "anti-white" began circulating a petition demanding that Bellamy resign or be removed from office. The petition ultimately failed and Kessler went on to organize the Unite the Right rally.