Chittenden CountyIn eight counties, the high bailiff candidate is running unopposed, while in four others, there are no candidates at all. None of that compares to the five high bailiff candidates running in Chittenden County. While the high bailiff position is obscure, McManus said the officeholder should be present in the community and have a deep familiarity with the way the state’s largest sheriff’s office works. Helaine Rappaport, a retired teacher of 50 years, does not see the high bailiff as anything more than a ceremonial title. Orange CountyIn Orange County, meanwhile, there’s no indication the high bailiff is in position to provide the services required of the office.