Democrat Timothy Holland wins Oxford County sheriff race over Wainwright

A 68-vote shift ousts lightning-rod Maine sheriff

The election results showed Democrat Timothy Holland winning Oxford County sheriff by 68 votes over Republican Christopher Wainwright. Democrat Timothy Holland, a 45-year police veteran, was declared the winner in the race for Oxford County Sheriff by a razor-thin 68-vote margin over incumbent Republican Christopher Wainwright. The stunning upset, reported by The Maine Monitor, marked voters’ first chance to weigh in on Wainwright since he survived a historic attempt to remove him from office two years ago. The race, which initially appeared to be heading for a recount after a morning Facebook post from Holland showed him trailing by just 12 votes, ultimately concluded with Holland securing 33.9% of the vote to Wainwright’s 33.7%, with independent candidate Justin Brown capturing 29.5%.

The weight of a three-way race

Both Holland and Brown had campaigned on the idea that a split vote would hand Wainwright a third term, a concern that felt particularly urgent given the sheriff’s tumultuous tenure. Instead, it was that very three-way dynamic that doomed him. The razor-thin margin between Holland and Wainwright, combined with a significant independent bloc, created a perfect storm for an upset. Holland, a school resource officer, managed to pull ahead despite the mathematical odds that often favor incumbents in crowded fields. Wainwright, of Dixfield, joined the sheriff’s office at 19 and spent 36 years there, rising to lead after the FBI investigation into his predecessor, then-Sheriff Wayne Gallant, who resigned in 2017 over sexual harassment allegations.

Democrat Timothy Holland wins Oxford County sheriff race over Wainwright — Photo: yahoo.com

Wainwright said early Thursday that he respected his Democratic opponent. The statement stood in stark contrast to the bitter campaign he waged against his own deputy, Justin Brown.

A history of controversy

This election was, in many ways, a referendum on Wainwright’s leadership, a story that has unfolded over the past four years. In 2022, he pressured a deputy to dismiss a traffic ticket for a woman he had grown up with and then berated the deputies who reported it in a recorded phone call. A year later, the Bangor Daily News discovered he had dispatched officers lacking certification into educational institutions and exchanged firearms from evidence to a gun shop in return for store credit with an almost complete absence of documentation. A county investigator concluded Wainwright may have committed theft, though he was never charged. The all-Republican Oxford County commission, alarmed by these events, unanimously asked Gov. Janet Mills to remove him in February 2024. Mills, a Democrat, called his conduct unprofessional but said it didn’t meet the constitutional standard for removal, famously declaring that voters, not the state, should decide his fate.

Democrat Timothy Holland narrowly wins Oxford County Sheriff's race by 68 votes

The civil rights complaint from three deputies, including Brown, alleging illegal retaliation, loomed large over the campaign. Brown and Wainwright traded frequent barbs on the campaign trail, with the sheriff leveling accusations against his deputy of conducting a smear campaign and referencing Brown’s involvement in a police shooting. Holland, however, ran a more positive campaign, and his friendship with Wainwright was noted by observers. The Monitor’s reporting, supported by the Bangor Daily News, highlighted that the sheriff’s race was just one part of a larger Democratic surge in the traditionally conservative county. In another closely contested race, Democrat Beth Bosworth won an open seat over former Rep. John Andrews, and party candidates also flipped three House seats based in Norway, Fryeburg, and Bridgton.

What’s next in Oxford County

A recount is all but certain in the sheriff’s race, a standard procedure in such a tight contest. The outcome, however, seems unlikely to change the final result.