Wrapping a noteworthy political career: Siller reflects on accomplishments and controversies

Gerry Siller wraps up a remarkable Shelter Island political career when his term as supervisor ends on Jan. 1. Mr. Siller looked back recently at his time in office with a sense of accomplishment, he told the Reporter last week.

Any fair-minded observer would have to agree there were multiple achievements in his time in office — along with a fair share of controversies — when Mr. Siller, a Democrat, was elected in November 2019, defeating Republican incumbent Gary Gerth by a total of 57.6% of the vote to Mr. Gerth’s 42.3%. He was then re-elected for a second term beginning in January 2020, running unopposed, a credit to his then-popular standing with the public.

Earlier this year he lost a Democratic primary against Gordon Gooding, who was defeated by Councilwoman Amber-Brach Williams in the general election.

This last go-round was his second residency at Town Hall as supervisor; he originally served from 1998 to 2001.

For his second two terms in office, Mr. Siller said, “I’d have to say my major accomplishment was leading the town through the COVID pandemic. Because of my experience having previously served as supervisor, I was able to step right in and work with [Police Chief] Jim Read and [Deputy Supervisor] Amber Brach-Williams to form the Emergency Command Team that interacted with the state, county and local institutions. We instituted safety procedures, sometimes ahead of the county and state, and were able to keep our residents safe.”

One of the brightest moments in memory on the Island was in February 2021 during the pandemic when Mr. Siller led the campaign to secure the largest inoculation site on the East End at the time with 500 doses of Pfizer vaccine administered at the school.

All agreed the event ran like clockwork, with town and school staffers volunteering (along with private citizens) to manage the event without a hitch. The booster inoculation event later was also smooth sailing all the way.

As for his first experience as supervisor at the turn of the century, Mr. Siller can also take credit for many accomplishments. Mr. Siller noted that during his first term he set to work implementing and extending the good work of his predecessor in the job, Hoot Sherman.

“Hoot got the affordable housing on Bowditch Road and started the Ram Island Causeway from the Army Corps and we followed through on it,” Mr. Siller told the Reporter’s Charity Robey. “We petitioned LIPA and they buried the power lines. We wrote the zoning code and created the near shore overlay district to protect the fragile areas.”

He also turned the Recycling Center around from a money drain to a money maker with the help of Brian Sherman’s skill for finding markets for the town’s recyclables. When a funeral home in the Center came on the market, Mr. Siller oversaw the purchase of the building as a new Town Hall, allowing the Police Department to emerge from the basement of their current headquarters.

During his current term he continued to fight for an affordable housing plan, which is now underway, and to work on clean water initiatives.

Criticized for being secretive with plans and policies before allowing the public access to information, and running contentious public meetings with what some have said was an overbearing and angry attitude, Mr. Siller categorically rejects those charges.

He said he was proud of the work he and Town Board members — including Mike Bebon who resigned in 2021 — have done. “This Board had the strength to identify and address the current needs of the Town, despite being attacked on numerous occasions by a small, but very well-funded, organized, and vocal group, who didn’t agree with our vision,” Mr. Siller said.

He admitted to being bothered by what he sees as unfounded charges leveled against him, and that the group referred to above publicly called him “a tyrant, rude, a bully and so on. The reality is, if anyone took the time to watch the actual exchanges at the meetings, they would see that I never initiated any hostility. What I did do was not back down to those who chose to be rude, tell untruths, or try to disrupt meetings. Basically, I gave back what was being thrown at the Town Board and those on the receiving end didn’t like that.”

To say his time in office has produced loud, theatrical and sometimes angry times wouldn’t be wrong. But it has not been unique — those remembering the administrations of Jim Dougherty can remember not a few shouting matches in the meeting room.

There have been fireworks at Town Hall, for example when Mr. Siller asked a police officer to remove a resident speaking at the podium, but then backed off, even as the officer was preparing to escort the resident out of the building.

And an extraordinary three-week period in the spring of 2021 when there was a rush of resignations — five in all — from appointed and one elected posts. (Councilman Mike Bebon cited family responsibilities for leaving after it was found that he had violated the town code by sitting as a committee chair while also serving on the Town Board.) The swinging door of people leaving their posts began with the departure of Edward Hindin as project manager of the Comprehensive Plan group after a June meeting marked by anger and accusations.

The Town Board subsequently put the entire Comprehensive Plan effort on hold. On the heels of Mr. Hindin’s resignation came Mr. Bebon’s statement that he was leaving the Island to be near family members.

Kathleen De Rose subsequently resigned from the Comprehensive Plan Committee, and another shock came when Peter McCracken resigned from the Community Housing Board. Close observers of town government said the situation at Town Hall had been poisoned by infighting and constant accusations by some residents of malfeasance.

Few would disagree with Mr. Siller that times have changed on Shelter Island. “The actual job of working in town government has changed tremendously since my first time in office,” he said. “Not only have the demands and the need for new technology grown, but the general attitude of the public has changed dramatically.”

He and his colleagues, he added, agree “that there is a new minority of very vocal citizens, usually with their own agendas, a lot of time and a lot of money, who have taken it upon themselves to disrupt any town actions they don’t agree with.”

He characterized some of the disruptions as excessive Freedom of Information requests, legal actions, and organized comments to “take over meetings, as well as full page ads in the Reporter — but usually choosing not to identify themselves in these ads. To say the least, it’s extremely frustrating to know that everyone serving on the Town Board is there to serve the town and address its needs. To be continually accused of having our own agenda is really quite perplexing. What possible motive might there be for personal agendas?”

(Note: All political ads in the Reporter identify the person or committee paying for them.)

Confident of his achievements, Mr. Siller is also confident that policies begun in his administration will make his hometown a better place. “While we’ve gotten a number of projects started, I look forward to the Community Housing Board continuing their good work and starting their first projects,” he said. “I also look forward to the Town working with the Suffolk County Water Authority to address the drinking water needs on the Island. Most importantly, I look to the CPF Advisory Board to address the drinking water needs here, through protection, re-charge or well fields. It’s been acknowledged on all fronts that the need for land preservation has been adequately addressed and the need for quality water is now paramount.”

As his term in office is coming to an end, Mr. Siller had nothing but praise for his Town Board colleagues. “I’ve worked with numerous individuals on different Town Boards and I have to honestly say the current Town Board works better as a team than any of the others I’ve been involved with.”

His fellow board members all had strong opinions “and were not afraid to express them,” he said. “Everyone was willing to do whatever work was needed to get the job done. Everyone knew what their role was and were there to do what was best for Shelter Island. And, contrary to what some of those out there say, each Town Board member thought for themselves and, I can honestly say, were never influenced or intimidated by me to vote as I saw fit. Most importantly, every member was always willing to stand up for what they believed in. It’s been a true pleasure working with each one of them.”