In Unusual Fashion, Two Vie for Presidential Seat on Southampton School Board

icon 2 Photos
Southampton Board of Education member Cara Conklin-Wingfield explains why she should be elected president, as member SunHe Sherwood-Dudley looks on.

Southampton Board of Education member Cara Conklin-Wingfield explains why she should be elected president, as member SunHe Sherwood-Dudley looks on.

Southampton Schools District Clerk Amy Pierson swears in Jacqueline Robinson as president of the Board of Education.

Southampton Schools District Clerk Amy Pierson swears in Jacqueline Robinson as president of the Board of Education.

authorMichelle Trauring on Jul 10, 2024

For the first time in recent history, a pair of Southampton School Board members faced off for the president’s seat last week, ultimately splitting votes among the seven board members into two camps.

Four board members voted in Jacqueline Robinson as president. She had helmed the board before SunHe Sherwood-Dudley, whose two-year tenure as president just expired.

Cara Conklin-Wingfield, who also was seeking the president’s seat, was ultimately voted in as vice president.

“I know it’s unusual to not have a unified plan going into the election,” Conklin-Wingfield said, “and I expressed interest in a leadership role with the board solely in the hope that we could be unified, and I’m sorry that didn’t happen.”

At the start of the organizational meeting on July 2, Board of Education newcomer Robert Zachary Epley nominated Robinson as president, quickly followed by a nomination for Conklin-Wingfield by board member Monique Proctor.

Conklin-Wingfield made her appeal for the seat, explaining that her intent was to help the “entire board be fully engaged and equally engaged.” She said she felt inspired after high school graduation, listening to the students speak about the adversity and challenges they faced — and “how they came through embracing change.”

“When I walked out of graduation, I felt like that’s what we should do, too,” she said, “because the board is in transition, the school district is in transition, I think the community is also in transition.”

On July 8, the district welcomed its new superintendent of schools, Dr. Fatima Morrell, whose appointment came on the heels of a fiery public meeting in April. At that meeting, members of the Parent Teacher Organization and others had voiced apprehension about the administrator, who gained international recognition in 2021 for her emancipation curriculum. A year later, Time magazine recognized the educator as a National Innovative Teacher.

During the meeting, Robinson voiced anger at the lack of community attendance at a forum that sought to solicit feedback on the superintendent search — and cited frustration over the hiring process as her reason for casting the sole dissenting vote in Morrell’s appointment.

She stood by that reasoning when Proctor asked Robinson for her motive behind wanting to lead the board.

“My motive is the same as always: to work together with my fellow board members and do what is best for all children,” Robinson said.

Later, she added: “We had a big meeting where we had our community involved and our teachers, and their words meant nothing in the end. The decision was already made, and we wasted a lot of time for a lot of people.

“And that’s why I voted no — and I made that clear at that meeting. It has nothing to do with her. I’ve spoken to her after the meeting. I wish her much success. I will do everything in my power to help support her and make our district continue to grow and be strong.”

Sherwood-Dudley came to Robinson’s defense, denying any public perception that Robinson does not support Morrell.

“Knowing Jackie as long as I have, and having seen how she operates, I think that she’s the perfect person to be president,” she said. “Because if we’re going to heal this divide or this conflict that runs within the board, she is the person to do so because of the misconceived perception that she does not support Dr. Fatima Morrell.”

While Epley said that, as the district navigates new leadership, it would be helpful to have a president with past experience, board member Germain Smith noted that Conklin-Wingfield has the most experience on the board outside Sherwood-Dudley and Robinson, and called into question Robinson’s reason for not voting in favor of Morrell.

“I have to go by your face value and your word that you only made that decision because of your feelings on the process, which I respect that,” Smith said, “but we did go above and beyond as a board, and I think it is time for change and new leadership.”

While the board members debated, Pierson looked up the proper procedure for moving forward with a vote.

“This is new in this process for this board, since I’ve been district clerk,” she said, “so I just wanted to let you know that I did look into Robert’s Rules of Orders to find out what to do if we had two nominees.”

She opted for an audible roll-call vote, starting with the first nominated candidate — Robinson. Four votes were needed to secure the seat, which came from the candidate, Sherwood-Dudley, Epley and newcomer Ruth White-Dunne.

Facing Smith for the vice-presidential seat, Conklin-Wingfield secured the role with votes from herself, Robinson, Epley and White-Dunne.

You May Also Like:

A New 27east and More Big Changes for The Express News Group

The Express News Group is launching a brand-new 27east.com this month, a major step forward ... 13 Dec 2025 by 27Speaks

Fractures Showing on Southampton Village Board Over Issues Like Meeting Agendas, Records Release, Workforce Housing and More

There was a period of time, not too long ago, when the Southampton Village Board could be counted on to pass almost any resolution or legislation with a 5-0 vote. It happened so frequently, in fact, that many residents began to question if that kind of uniformity of thought was healthy for the village, or if it was a sign that the art of dissent had been lost, along with a willingness to thoughtfully examine both sides of any given issue. One thing’s been made clear in the second half of the calendar year — that period of smooth sailing ... 12 Dec 2025 by Cailin Riley

East Quogue Engineer's Dazzling Light Show Brings Joy and Raises Money for St. Jude Children's Hospital

​When Joseph Commisso was a child, growing up in East Quogue, he remembers making a ... by Cailin Riley

Southampton Police Reports for the Week of December 11

WESTHAMPTON BEACH — Dario Vasquez, 26, of Hampton Bays was arrested by Westhampton Beach Village Police on December 9 and charged with driving while ability impaired by alcohol, a misdemeanor. At 1:09 a.m., Police said they observed a blue Chevrolet Silverado traveling west on Mill Road in an unsafe manner by failing to maintain its designated lane. Officers conducted a traffic stop at the intersection of Mill Road and Wayne Court. The driver exhibited signs of intoxication and was placed under arrest, according to police. FLANDERS — Walmer Santos-Alvarez, 25, of Riverhead was arrested by Southampton Town Police at about ... by Staff Writer

Southampton Community Packs a Truckload of Holiday Cheer for Families in Need

Southampton Town residents have once again shown their generosity by contributing to the Southampton Town ... by Staff Writer

Harmony for the Holidays

Let’s be real: As jolly as the holidays can be, they can also be overwhelming. ... by Jessie Kenny

Dear Neighbor

Congratulations on your new windows. They certainly are big. They certainly are see-through. You must be thrilled with the way they removed even more of that wall and replaced it with glass. It must make it easier to see what is going on in your house even when the internet is down. And security is everything. Which explains the windows. Nothing will make you feel more secure than imagining yourself looking over the rear-yard setback from these massive sheets of structural glass. Staring at the wall has well-known deleterious impact, and windows the size of movie screens are the bold ... 11 Dec 2025 by Marilee Foster

I Can Dish It Out

Our basement looks like the final scene in “Raiders of the Lost Ark,” where the (found) ark is crated and wheeled into the middle of a government warehouse with stacked crates going on for miles. In other words, we have a lot of stuff. This tracks. Mr. Hockey and I have been married for 36 (according to my calculator) years. We’ve had four (no calculator needed) pucks. We’ve lived in seven (according to my fingers) different homes in three (no calculator or fingers needed) countries. In 2010, we moved back to East Hampton full time. We brought everything we had ... by Tracy Grathwohl

The Urgency of Real

The Hamptons International Film Festival typically takes up a lot of oxygen in the fall on the South Fork, but it’s worth celebrating a slightly smaller but just as vital event in late autumn: the Hamptons Doc Fest. Running this week for its 18th year, the festival of documentaries was founded by Jacqui Lofaro and has become an essential part of the region’s arts scene every year. It’s a 12-month undertaking for Lofaro and her staff, and the result is always a tantalizing buffet of outstanding filmmaking, not to mention unforgettable stories. The arrival of the era of streaming services ... 10 Dec 2025 by Editorial Board

Proceed With Caution

Overlay districts are a common zoning tool used by many municipalities. Southampton Town has used them to varying degrees of success — the aquifer protection overlay district has been a winner; a downtown overlay district in Hampton Bays less so — in various parts of the town. They essentially look at the existing zoning, then allow those rules governing what can be done on properties to be reconsidered if there’s a newer concern to be addressed. In a bid to clean up the process for creating more affordable housing, the Town Board is looking at a new overlay district that ... by Editorial Board