In 1990, Dowless was convicted of felony perjury, and in 1992, he was convicted of felony insurance fraud. He was sentenced to two years in prison for the latter charge, and served six months. Dowless began working in politics in 2006, focusing on get out the vote efforts. In 2006, he worked for Rex Gore's campaign for district attorney of Bladen County. Over the next couple of years, Dowless was paid thousands of dollars for get out the vote efforts and, at times, campaign manager for eastern North Carolina candidates Wesley Meredith, Al Leonard, Ken Waddell, and William Brisson. In 2010, he worked for Harold Butch Pope's campaign for district attorney. When asked why he chose to work for Harold Butch Pope over incumbent Rex Gore, who he previously worked for in 2006, Dowless said Gore was a "God Damn Snake" and "Lied As Soon As He Helped Him Get Re-Elected". In 2014, Dowless worked for Jim McVicker's campaign for sheriff. McVicker won by a small margin, and allegations were made about mishandled absentee ballots. Dowless himself was elected to the Bladen County Soil and Water Conservation Board in 2012 and then re-elected in 2016.
After noticing that Todd Johnson had won the absentee vote in Bladen County in 2016, Harris had a consulting company, Red Dome Group hire Dowless to work on his 2018 campaign. Harris introduced Dowless to a Republican candidate running for Charlotte City Council in 2017.
Primary election
In the 2018 primary election, Harris defeated Pittenger, although doubts have since surfaced regarding Dowless' role in absentee balloting in the primary, in which Harris received 437 of the 456 absentee votes cast in Bladen County.
General election
In the general election against Democratic Party nominee Dan McCready, Harris was the unofficial winner by 905 votes. However, the Board of Elections refused to certify the results of the election. Dowless is accused of paying workers to illegally collect absentee ballots from voters. and is considered a "person of interest" in the investigation over mishandled absentee ballots. On February 4, the newly seated state elections board set an evidentiary hearing to begin on February 18. On the first day of the evidentiary hearing, state elections director Kim Strach said the evidence would show that "a coordinated, unlawful and substantially resourced absentee ballot scheme operated in the 2018 general election". Lisa Britt, the daughter of Dowless's ex-wife as well as one of his employees, said Dowless and his associates had collected ballots from voters. She then testified that the ballots were kept at Dowless' home or office for several days or longer, and that operatives would fill in votes on parts or all of some ballots to favor Republican candidates in the election. She also said they had forged some witness signatures and that they had followed the direction of Dowless to take steps to avoid detection, including controlling the color of the pens used for the witness signatures, signing a different person's name as a witness to avoid having the same person as witness to too many ballots, making sure to deliver only no more than nine ballots in each visit to the post office, and making sure to use post offices near where the voters lived. Britt also said she had personally voted despite being on probation for a felony conviction and that she had taken advice from Dowless about how to do that. Dowless himself was present at the hearing but refused to testify without being granted immunity from prosecution.
Indictments
On February 27, 2019, Dowless was arrested after being indicted by a Wake County grand jury. Dowless was charged with multiple counts related to illegal ballot handling and obstructing justice in the 2016 and 2018 elections. An additional four people who worked for him were also charged. In July, additional charges of perjury and solicitation to commit perjury were added in a superseding indictment. On April 7, 2020; Dowless was indicted on federal charges of Social Security fraud. In the indictment, unsealed on April 21, prosecutors alleged that Dowless claimed disability and retirement benefits in 2017 and 2018, but failed to tell the Social Security Administration about over $132,000 in payments he received for working on the Harris campaign and one other campaign for in the 2018 cycle.
