Two years after Gov. Janet Mills declined to remove him from office and said Oxford County voters should decide his fate, Sheriff Christopher Wainwright is asking for a third term.
The Republican sheriff, whose tenure has drawn multiple Bangor Daily News investigations since his high-profile role in blowing the whistle on his former boss, may face an easier path because he has two challengers on Nov. 3: Deputy Justin Brown, an independent who lost to him by 344 votes in 2022, and Democrat Timothy Holland, a 45-year police veteran.
The race is the first time voters get to weigh in on Wainwright since he survived Maine’s most serious attempt to remove a sheriff in nearly a century. The general election for sheriff isn’t decided by ranked-choice voting. That means Brown and Holland could split the vote against Wainwright in a county he carried narrowly four years ago.
Both challengers know that split could hand Wainwright a win. Holland said his campaign is going well but that he’s “highly concerned” that votes against Wainwright will be divided between him and Brown.
“Obviously that’s going to split votes,” Brown said of Holland’s presence in the race. “Either way, I do hope that the citizens of Oxford County are fortunate enough to get a new sheriff because it’s long overdue. It’s desperately needed.”
Wainwright, of Dixfield, joined the sheriff’s office at 19 and has spent 36 years there. He rose to the top out of the office’s biggest scandal. In 2017, when he led its criminal investigation division, he was involved in an FBI investigation into then-Sheriff Wayne Gallant, who was accused of sexually harassing several people.
Wainwright later testified about what investigators found, and he emerged as a leader in the office after Gallant resigned that year. Gallant quit before then-Gov. Paul LePage could act on the commissioners’ request to remove him. Wainwright won the open seat in 2018.
Within four years, his own conduct was under scrutiny. In 2022, he pressured a deputy to dismiss a traffic ticket for a woman he’d grown up with. When that deputy and another reported it up the chain of command, Wainwright berated them in a recorded phone call.
More revelations followed in 2023. The BDN found that Wainwright had sent uncertified officers into schools with guns and badges. It also found he had traded guns and gun parts from evidence to a gun shop for credit without notifying owners or the county, and with almost no paperwork.
A county investigator concluded that the trade broke state law and that Wainwright may have committed theft, though he was never charged. In February 2024, the all-Republican county commission unanimously asked Mills to remove him. After a hearing run by a retired judge, Mills, a Democrat, called his conduct unprofessional but said it didn’t meet the constitutional standard for removal.
Wainwright called the decision a vindication. Two months after Mills ruled, commissioners refused to pay his legal bills from the removal fight. The county also settled a sex-discrimination lawsuit in 2024 from a former clerk who said Wainwright tried to fire her for criticizing him.
Mills’ decision left Wainwright in charge of the deputies who had cooperated with the investigation against him. Brown was one of them.
In August, he and two colleagues filed complaints with the Maine Human Rights Commission. They allege that Wainwright escalated discipline against them after he kept his job, and that the county didn’t protect them. The sheriff has called the complaints a political attack.
Brown was demoted from lieutenant to deputy in 2025 over his role in a police shooting and hasn’t worked since last October, when he was put on leave over a weapons allegation. A state panel dismissed a related challenge to his truthfulness in July, but Wainwright suspended him for 90 days without pay in August.
Brown is running as a change candidate. His recent campaign materials focus on lowering costs, cutting unnecessary overtime and maintaining professionalism. In a recent Facebook video, he said “employees don’t quit bad jobs, they quit bad leadership or bad bosses.” Holland says he’s also running for change. His campaign has garnered many endorsements, including some from beyond his party, which he shares on Facebook.
Wainwright’s campaign has focused on his work, sharing statistics about high call volumes and partnerships with local police. He’s confident he’ll win, acknowledging the split field may help him, and he also said the headline-grabbing parts of his record are not coming up on the campaign trail.
He criticized Brown for running a more negative campaign than his own and Holland’s, although he noted his deputy’s role in the shooting unprompted during an interview.
“I’ve kept it clean and positive, and that’s what I’m going to continue to do,” he said.
Daniel O’Connor is a Report for America corps member who covers rural government as part of the partnership between the Bangor Daily News and The Maine Monitor, with additional support from BDN and Monitor readers.