Shelter Island town supervisor candidates

BEVERLEA WALZ PHOTOS | Supervisor candidates (L-R) Bob DeStefano, Jim Dougherty and Glenn Waddington

This week the Reporter presents the responses of the three candidates for town supervisor to a questionnaire sent to all Town Board candidates early in October. Biographical outlines appear below based on the candidates’ responses. Their answers to questions about specific Island issues and concerns appear on the following pages, grouped according to each question.

The supervisor is the town’s chief fiscal officer who must prepare a preliminary budget every year and submit it to the town clerk’s office in late September. Otherwise, the supervisor has no greater power than any Town Board member in the sense that he or she is one of five equal votes. However, the supervisor manages the Town Board’s meeting agenda, subject to other board members’ requests; runs the board’s meetings; and handles many ceremonial, political, administrative and financial tasks. With a salary of $70,000, the supervisor is considered the board’s only full-time member and serves a two-year term, unlike the councilpersons, who serve four-year terms.


Age: 72

Where you grew up: Long Branch New Jersey.

Education: Long Branch High School, 1957.

If you moved to Shelter Island, when and why: I moved to Shelter Island in 1962 because I was given the opportunity to become the head golf professional at Gardiner’s Bay Country Club. I stayed on Shelter Island for 50 years because I fell in love with its natural beauty and sense of community and realized that it was the perfect place to raise my children.

Family: Anne, my wife of 53 years, has worked with me at Gardiner’s Bay. She is also a real estate broker and was previously part-owner of Hallock Real Estate. She is a past-president of the PTSA and was a Scout leader. My son, Bob (42), graduated Shelter Island High School and has his own law practice in Mineola. His wife, Elena, volunteers at the Shelter Island Public Library. My daughter, Nancy (40), also graduated Shelter Island High School. She is married to Kevin Byrne and living in East Hampton, She previously worked as a clerk for the Shelter Island Police Department and served on the Deer and Tick Committee.

Work and career: I have been the head golf professional at Gardiner’s Bay Country Club since 1962, establishing a national PGA record of 50 years as head professional at the same club. Prior to moving to Shelter Island, I was an assistant golf professional at Southampton Golf Club for two years; I served two years in the United States Coast Guard.

Hobbies and interests: Any free time that I have I like to spend with my family, whether taking short trips, playing games or just sharing a meal. I also like to travel and, unsurprisingly, to play golf. I also occasionally play cards with friends. I would rather read than watch TV and prefer biographies and non-fiction.

Awards: PGA Golf Professional of the Year (the PGA’s highest award); PGA Junior Golf Leader of the Year; PGA Merchandiser of the Year; PGA Magazine Community Leader; USKids Top 50 Kids Teachers in America; Eastern Long Island Hospital Man of the Year.

Elected offices: Shelter Island School Board president (six years), member (15 years).

Community service: 20-year member of the Lions Club and the American Legion.


Age: 74

Where you grew up: Baldwin, Long Island.

Education: Baldwin High School; Dartmouth College, A.B., political science; Columbia Law School, DL; Harvard Business School, Advanced Management Program.

If you moved to Shelter Island, when and why: 1976, second home; permanent 2001.

Family: wife, Nancy.

Work and career: Lawyer, Hughes, Hubbard & Reed, New York City; general counsel, Supermarkets General Corp.; senior vice president, executive vice president, president, Supermarkets General Corp.; retired 1990.

Hobbies and interests: Tennis, sailing, reading, environmental preservation.

Community service: Chairman, Community Land Preservation Board (2% Committee) 1999–2007; member, Shelter Island Comprehensive Plan Committee, 1992-94; chairman, Zoning and Open Space Subcommittee, 1992-94; chairman, South Fork, Shelter Island Chapter, The Nature Conservancy, 1992-95; a founder and chairman of board, the Peconic Baykeeper, 1998-2002; member of board of directors, New York League of Conservation Voters, 1995-1998; volunteer, Project Hope–State Department, in Riga, Latvia, March 1992; volunteer, International Executive Service Corps in Siberia, Russia, October–December 1996 and in Cairo, Egypt, October–December 1998; LTJG, U.S. Navy Reserve, two years active duty.


Age: 62

Where you grew up: Shelter Island.

Education: Shelter Island High School 1967; SUNY School of Forestry 1967-1969; Syracuse University, B.A., history 1971; Southampton College, 1972-1973, elementary education.

If you moved to Shelter Island, when and why: 1958, from Ohio with my mother and two sisters when I was 10. That move was one of the best things to ever happen to me.

Family: My wife Gwen is co-owner of the Wharf Shop in Sag Harbor and our son Morgan graduated valedictorian from Shelter Island High School in 2009. He is a junior at Tulane University where he received a presidential scholarship. He recently was awarded a full scholarship from the Marine Corps ROTC. My mother grew up on Shelter Island and moved our family back here in 1958. I have many relatives spread among a number of families, among them the Dickersons, Cases, Clarks and Conrads.

Work and career: Upon graduating from Syracuse I made application for a teaching position at a number of area schools. While waiting for an opening, I went to work for South Ferry Inc. I soon realized that I enjoyed piloting the boats and have stayed with the ferry for the last 40 years. I am now the senior captain. About 20 years ago, I was tasked with creating a new pilot training program and have taught over 30 new boat operators at South Ferry. And of course I have been your councilman for 12 years.

Hobbies and interests: I enjoy reading both history and fiction, fishing, target shooting, archery, reading, and riding my motorcycle. My interest in history aids me in an understanding of our society.

Awards: Bowling trophy for the Thunderballs back in the 1970s.

Elected offices: I was elected councilman for three terms: two four-year terms 1994-2001, after which I chose not to run again in order to spend more time with Gwen and Morgan while Morgan was growing up. My third term began January 1, 2008 to the present.

Community service: I have contributed my energy to the Shelter Island community as a member of the Mashomack Preserve Advisory Committee, member of the Friends of the Shelter Island Library, member of the Shelter Island Public Library Board, member of the Shelter Island Zoning Board of Appeals and a member of the Shelter Island Comprehensive Plan Committee.

Many people remember Supervisor Hoot Sherman, Councilperson Sharon Kast and I were responsible for the creation of the Shelter Island Land Preservation Fund (the 2 Percent Fund). As a councilperson, I voted to preserve Section 9. I also voted not to sell Taylor’s Island.

I also lobbied for and voted for the starter housing program on Bowditch Road. In partnership with Councilperson Lewis, we created Shelter Island’s first community housing law.

I am a member of the Shelter Island Presbyterian Church and sing in the church choir.