Politics have never been more local than the race for town clerk in Olive, where the 12-year incumbent flipped to the Republican ticket after losing the Democratic primary in June by a 3-to-1 margin.

“I’m not a liberal and I’m not a conservative,” said Dawn Giuditta, 58, who has worked for the town in various roles since 1989. “I am an Olive resident. I just want to serve the community I’ve known my whole life.”

Kimberly Daley, Democratic candidate for Olive town clerk and tax collector, will face incumbent Dawn Giuditta in the November election. Photo courtesy of Kimberly Daley.
Dawn Giuditta, incumbent Olive town clerk and tax collector, is seeking reelection in November after switching to the Republican line following her loss in the Democratic primary. Photo courtesy of Dawn Giuditta.

The decision by Giuditta, who will face off in November against Democrat Kimberly Daley, 55, isn’t just another small-town political squabble. It underscores a larger debate over party affiliations in rural areas, New York’s failure to enact “sore loser” laws and the ever-present divide between lifelong residents and newer arrivals. 

Giuditta, who grew up in West Shokan and lives in Samsonville, said as early as 2016, she started becoming disillusioned by how state and national politics had crept into local governance. So when she lost the primary to Daley, it didn’t feel like that much of a leap to cross the aisle. She’s also at odds with Mary Anne Shepard, 71, co-chairman of the Olive Democratic Committee, and says her standing with Democrats has eroded since she chose to skip vaccinations during Covid.

Olive Democrats practice “our way or the highway,” Giuditta said. “I feel like I’m running against the committee.”

Shepard downplayed any part played by Giuditta’s anti-vaccination stance in her decision to switch parties.

“It was more about how she did her job and whether she was really a Democrat,” she said.

The back-and-forth could have been avoided if New York, like 48 of the 50 U.S. states, had enacted a law to bar primary losers from running in general elections as an Independent or another political party. Its absence explains why former Governor Andrew Cuomo, the loser in New York City’s Democratic mayoral primary for mayor, is staying in the race as an Independent.

Daley, for her part, praised Giuditta’s decision because it gives voters another choice. The 55-year-old has campaigned on modernizing the clerk’s office by digitizing records and recording meetings. Olive’s town clerk also includes serving as the town’s tax collector. 

“Her seeking another party line was a good strategy,” Daley said. “The lack of ‘sore loser’ laws is allowing Olive residents to have that.”

The election has also exposed the fissure between locals and those to whom some communities simply refer to as having come from “away.”

“I have lived here 45 years and I’m not considered a local,” Shepard said with a laugh. “There are still people in this town who are very upset with anyone who is a newcomer.”

Daley, 55, works for a vacation rental management company 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.

A few “old-school” residents resent local political candidates who are perceived as outsiders, said Robert Fehring, 66, who has lived in Olive for 45 years and is running as the Republican candidate for town supervisor against incumbent Democrat Jim Sofranko.

“It never bothered me” that Giuditta was a Democrat, Fehring said. Still, some residents wonder, “Why is someone from the city trying to take her job?”

Jim Rich is a reporter for The Overlook. You can reach him at jim@theoverlooknews.com.


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