Richard LaManna III wants to be a sheriff in the worst way—that’s why he’s this week’s Rogue.

Last fall, LaManna—whose family made a fortune in the marina business—explored running for sheriff in Washington County. That made sense because LaManna, 48, had worked from 2000 until 2006 as a deputy in the Washington County Sheriff’s Office.

But in October, LaManna, whose residence was then an $805,000 house in Washington County, decided to run instead for Clackamas County sheriff.

To meet Clackamas County residence requirements, a candidate must establish residence a year before the Nov. 3 Election Day. So, on Oct. 26, 2007, LaManna rented a room in Milwaukie as that residence. LaManna’s move was opportunistic but not unheard of in the history of carpetbagging politicians.

But the friend renting LaManna a room, Joshua Henningsen, is also LaManna’s campaign manager and treasurer. LaManna says he looked for a home in Clackamas but was reluctant to commit in a shaky market. He insists he now lives in Henningsen’s basement.

So LaManna was set to run against incumbent Clackamas County Sheriff Craig Roberts. According to state election law, if there are going to be only two candidates, the election would be held in November.

If more than two candidates file, there would be a May primary. And on the March 11 filing deadline, Henningsen—LaManna’s landlord and aide—also filed to run. In that filing, he indicated he wouldn’t spend more than $300. LaManna acknowledges the filing looks unusual but says the two men’s goal was simply to let voters weigh in on a controversial new jail proposal before November.

Steve Thoroughman, who heads the county deputies’ union PAC, which supports the incumbent, says Henningsen’s candidacy is bogus. “They are trying to bend the rules to suit their own ends,” Thoroughman says. And that’s Roguish.