Olive Town Clerk Dawn Giuditta, who was unseated in November by challenger Kimberly Daley, unexpectedly resigned this week, stepping down a month before her term was set to end. Her deputy, Amanda Winne, also resigned.
Giuditta, who has worked for the town in various roles since 1989, surprised many over the summer when she switched parties to accept the Republican nomination after losing to Daley in the Democratic primary. At the time, she said she had grown disillusioned with Olive Democrats and suggested that some of that frustration had seeped into her interactions with town board members and Supervisor Jim Sofranko.
She said in an interview that she resigned because of that tension and out of concern that the board would not grant her health benefits if she finished her term. Olive employees are entitled to medical benefits in retirement if they have at least 20 years of service and are 55 or older.
“I don’t trust this town board,” Giuditta, 58, said. “I don’t like some of the games they played. They do things that I don’t always feel are appropriate.” She declined to provide specifics.
Sofranko, who on Tuesday named Daley as interim clerk, said Giuditta’s benefits package was never in question. He also downplayed her claims of workplace tension.
“I have no basis to address those claims,” Sofranko said. “I respect that Dawn put so much time into the town.” He said the town board plans to submit a letter of appreciation to Giuditta and Winne at next week’s board meeting.
“Elected officials are only judged by voters,” Sofranko said. “I had only hoped for a smoother transition.”
Daley said she asked Winne to stay on as deputy clerk, but Winne declined, citing lingering “hard feelings” and a “lack of communication” among town officials.
Winne declined further comment.
Winne’s husband, Chris, works for the town highway department and is chief of the Olive Fire Department. In 2015, he sought the Democratic nomination for highway superintendent but was passed over when the party endorsed Brian Burns, then a registered Republican. Burns switched his affiliation to Independent and went on to win the election. Several people familiar with the situation said that fallout created a long-running rift between the Winnes and some Democrats in town government.
Daley said she will name a new deputy at Tuesday’s town board meeting. To assist with the transition, she has tapped Shandaken Town Clerk Joyce Grant as an unpaid interim deputy. Grant is expected to spend “a few hours” this week walking her through the clerk’s duties.
Daley, 55, manages vacation homes in the area and has lived full-time in West Shokan since 2011. A Boston native and graduate of Babson College, she previously lived in New York City, where worked for Sweden’s Handelsbanken and Lehman Brothers. She’s served on the Olive Library board for 12 years.She has asked the town board to lower her salary from $69,000 to $63,000, saying she hopes to use the savings to improve services — such as video recording of town meetings and upgrades to the town website — without adding costs to the 2026 budget.
She said she empathizes with both Giuditta and Winne.
“I think Dawn and Amanda are good people and they love the town and its residents,” Daley said. “I hope, over time, the community can be better informed and move forward and appreciate the people that have worked before us and set the ground for people who come in the future to govern our town. If we are better communicators then the town will flourish.”
Jim Rich is a senior reporter for The Overlook. You can reach him at jim@theoverlooknews.com.