Southold Election 2023: Krupski wins Town Supervisor race

Suffolk County Legislator Al Krupski proved victorious over Republican candidate Donald Grim in the race for Southold Town supervisor. The Democratic and Conservative candidate will succeed Scott Russell, who served as supervisor for 18 years.

At a Democratic party celebration at Greenport Harbor Brewing Co. in Peconic Tuesday night, Mr. Krupski said, “My three children are here. They’ve given us six grandchildren and this is really the reason I’m doing this. You look to the future and this is our time here in Southold Town. You look at the great history of the town and this is our chance to make an impact — not just elected officials but everyone who cares about the town and wants to do something for it.”

In 1986, Mr. Krupski began his political career as a Southold Town Trustee, a position he maintained until he was elected to the Town Board in 2005. After seven years on the board, voters elected him to the Suffolk County Legislature in 2013, the position in which he currently serves. A fourth-generation farmer who owns Krupski Farms, environmental preservation has underscored his political career, from helping write a townwide drainage code that reduced road runoff into creeks and estuaries as a Town Board member, to supporting Suffolk County’s move to put $1 million toward coastal resiliency efforts as a legislator.

At a Republican party gathering at Sannino Vineyard, Peter McGreevy, Southold Town Republican chair, called for a round of applause for Mr. Grim — the sole Republican to throw a hat in the ring for supervisor when it appeared no one would. Mr. Grim manages and operates a recycling facility in Cutchogue and is a volunteer firefighter with the Cutchogue Fire Department. In 2021, he ran as the Republican candidate for Southold highway superintendent. As Mr. Grim parted ways with Republican supporters Tuesday evening, he said he felt “great” about his decision to run, regardless of the outcome, as it gave voters an alternative. “We’re all together in this,” he said. “I’m a team player. We went out and did our best, worked our hardest and let the chips fall as they may. I hope I see Al Krupski in King Kullen tomorrow morning and I’ll congratulate him.”

In the much closer race for Town Board seats, with absentee ballots not yet fully counted, it appears likely that Anne Smith and Jill Doherty will join Mr. Krupski on the board in January. Thus far, Ms. Smith is the top vote-getter, edging out Ms. Doherty by just 0.57%. 

Since she and her husband moved to Mattituck in 1985, Ms. Smith has served in numerous roles throughout the community. She retired as superintendent of the Mattituck-Cutchogue School District in 2018 after previously serving as assistant superintendent and elementary school principal. Among her other titles, Ms. Smith served as chair of the North Fork Coalition for Behavioral Health, advocating for local mental health services for families; president of the Mattituck-Laurel Civic Association; and a member of the Southold Town Police Review Task Force.

“I am really very excited about the possibility of serving Southold Town as councilwoman and member of a strong collaborative team,” Ms. Smith said Thursday afternoon. “We will all be watching the official  results closely and I am still rooting for my colleague Gwynn while looking forward to the possible opportunity to work with whatever team we have in place in January. Everyone cares so deeply about the future. There is critical work to do shaping the future. Al Krupski’s leadership and experience will guide us well.”

Ms. Doherty’s experience in town government spans several decades. Tuesday evening marks her sixth consecutive election campaign, her fourth as a Town Board member. She has been successful in all previous elections.

“This whole campaign has been positive all around,” Ms. Doherty said as the results appeared to be moving in her favor. “It’s been fun, I’ve knocked on over 1,200 doors and I’ve got a lot of feedback from a lot of people. ”

Ms. Doherty served 26 years with the Mattituck Fire Department Auxiliary and worked for local banks and as a bookkeeper before coming to Southold Town Hall as a clerk to the Board of Trustees. During much of her most recent four-year term as a council member, she played a key role in crafting and educating residents about the Community Housing Plan, a key step in tackling the town’s affordable housing shortage. “There’s a lot of work to be done and I would hate to leave during ongoing projects [such as] our overview of zoning,” Ms. Doherty said Wednesday morning.

“It’s really humbling and it’s really amazing the people who reached out to me, on both sides of the aisle, that support me. I’m truly here for them. It’s a special feeling knowing that they believe in me to be their voice and that they trust me.”

Tallies for the other two Town Board candidates were also tight, with Gwynn Schroeder and Stephen Kiely just 2.22% apart. Ms Schroeder has worked as a legislative aide to Mr. Krupski for the past 11 years. An advocate for the environment, she spent a decade working for North Fork Environmental Council, becoming the group’s executive director. She also helped pass the original Community Preservation Fund and was the key staff person for the Save What’s Left Campaign.

Mr. Kiely is currently the Shelter Island town attorney, the Mattituck Park District attorney and has been a municipal lawyer for several East End towns including Southold and Southampton and the Villages of Greenport and Westhampton Dunes, as well as an assistant district attorney. 

Tuesday evening, before the final results were in, Mr. Kiely said he felt “disappointed.”

“Who knows what the results will actually be?” he said. “I’m disappointed for the direction of the town that it’s going to go.”

Tuesday’s results expand on the Democrats’ historic victory in 2021, which upset the majority Republicans held on the Town Board for 14 years. That election marked the first time Democrats won six races in a single town election in at least 90 years. Now, Mr. Krupski’s victory as the town’s first new supervisor in 18 years tilts the board blue, with Justice Louisa Evans, representing Fishers Island, and Ms. Doherty in the minority. 

As of presstime, however, it appeared that absentee ballot counts could narrow the vote gap between Ms. Schroeder and Ms. Doherty, and possibly change that result.

Following a somewhat contentious campaign, incumbent Daniel Ross emerged victorious in the race for town justice. Mr. Ross was first elected to the position of Southold Town Justice in 2019. His experience includes his law practice in Mattituck for the past 37 years, his public service as a town Councilman and his municipal law experience as village attorney for Greenport. He has been a practicing attorney in the Supreme Court in Riverhead and the Southold Town Justice Court for more than 30 years. He is a member of the NYS Bar Association, the Suffolk County Bar Association and the NYS Magistrate’s Association.

The race for Suffolk County Executive has been called for Republican and Conservative candidate Edward Romaine, with a nearly 40,000-vote lead over Democratic and Working Families candidate David Calone, an entrepreneur and former federal prosecutor and New York State special assistant attorney general. Mr. Romaine, a four-term Brookhaven Town Supervisor, has a reputation as a fiscal conservative who has long supported both green energies and preserving open space. He will succeed Democrat Steve Bellone, who has reached his term limit after 12 years.

With 53.15% of the vote, Republican Catherine Stark is poised to win the race over Democrat Catherine Kent to serve Suffolk County’s 1st Legislative District. She will fill Mr. Krupski’s seat, which he has held for 10 years. Ms. Stark, a lifelong Riverhead resident, began working for Suffolk County in 1996, first for the Clerk of the Legislature and then for Penny Wells LaValle, director of real property tax services. For seven years, she served as chief of staff for former Suffolk County legislator Jay Schneiderman, who later became Southampton Town Supervisor. Since 2013, she has done the same for Mr. Krupski. 

Both Glenn Goldsmith and Albert “Nick” Krupski ran unopposed in their bids to maintain their seats on the town’s Board of Trustees. Both men were first elected in 2015 and work for multi-generational family businesses —; Mr. Goldsmith at Goldsmith’s Boat Shop, which celebrated its 100th anniversary earlier this year, and Mr. Krupski at his family’s farm. While Mr. Goldsmith ran as a Republican and Nick Krupski a Democrat, they were both endorsed by the Conservative party.

In another unopposed race, Kelly Fogarty will continue her tenure as Southold Town’s receiver of taxes. Ms. Fogarty, a North Fork native and a practicing certified public accountant for more than 30 years, was first elected to the position in 2019.

Democrat William Flinter prevailed in the race for Town Assessor over Republican opponent publican Michael Goscinski. A Mattituck native who earned his bachelor’s degree in finance from Siena College, Mr. Flinter has worked for a variety of financial institutions, including American Portfolios, Farm Credit East and, currently, M&T Bank.