He was also a contender for the Democratic nomination in 2008 Mississippi's 1st congressional district special election but he lost the primary runoff to Travis Childers.
[2] While serving as the elected county judge, his mother was targeted in the 2013 ricin letters incident, but she was unharmed.
[4][5] Early in his career, Holland helped pass legislation supporting organ donations in Mississippi.
[9] In March 2017, Holland announced that his doctors had diagnosed him with dementia, and that he would not seek re-election at the end of his term in 2019.
Holland's switch in party affiliation was speculated to be an attempt at avoiding a defeat to Thompson in the Democratic primaries, with the Daily Journal noting that Holland had "outspokenly identified as liberal" and, if victorious as an Independent, would have nonetheless been "certain to caucus with Democrats.