The Brief Nick Ollinger won Waukesha County’s Republican primary for sheriff on Tuesday night. Nick Ollinger won Waukesha County’s Republican primary for sheriff on Tuesday night, defeating John Gscheidmeier. With no Democrat in the race, the winner of Tuesday's Republican primary takes the job. What they're saying:Nick Ollinger has worked for the Waukesha County Sheriff’s Department for 13 years and is currently the captain of the Detective Bureau. They’ll say Waukesha County Sheriff’s Office is a place you want to be and work."