The Brief Two Republicans are running for Waukesha County sheriff. Both John Gscheidmeier and Nick Ollinger have law enforcement backgrounds. Two Republicans, John Gscheidmeier and Nick Ollinger, are running for Waukesha County sheriff. Related articleIn January, Waukesha County Sheriff Eric Severson announced his plan to retire at term's end. The Waukesha County Sheriff's Department serves nearly 410,000 residents and covers 567 square miles, according to its website.