A Long Island Vacation Hub for the One Percent Is Reeling From a Political Crisis

View of Dering Harbor. Photo: Google

With less than three weeks left before its annual election, with the mayor’s seat and two trustee slots up for grabs, the smallest incorporated village in New York State, Dering Harbor, is abuzz with talk of voter fraud.

The village is in modern Gatsby country: on Shelter Island, between Long Island’s two forks. Historically the province of robber barons, it’s now the vacationland of one-percenters, mostly from Manhattan, who have surged there over the last 15 years seeking a quainter and quieter alternative to the Hamptons; it’s also home to some old-money residents who stay there permanently. Its population is just 11, if you go by the latest U.S. Census — or about 72, if you go by the dubious voter rolls from the most recent mayoral election, in 2014, when neighbors accused each other of recruiting outsiders to register there and tilt the outcome.

There are residents who call village life the epitome of democracy. Anyone with a grievance can voice it at a town meeting, or even take it up with the mayor directly, said Kirk Ressler, a retired foreign service officer who splits his time between Shelter Island and Florida. “Do you live in New York City?” Ressler asked during an interview on his porch. “Where do you go to complain about the government?”

But the recent influx of Manhattanites has brought a culture clash. Some criticize the village government’s lack of transparency (it has no website, and dates of meetings and elections can only be found in the fine print in the back of the local newspaper) and say Tim Hogue, the mayor of some 26 years, uses the ordinances to harass those who vote against him — preventing them, for instance, from putting up shrubs or expanding their porches.

And more important, since the election fiasco of 2014, the Manhattanites have seen little point in voting, let alone mounting a campaign against Hogue, because they believe the elections are rigged. It seems the place has always been too small, and its affairs too inconsequential, for the state to seriously investigate. “It’s kind of a banana republic,” says Clora Kelly, a onetime dentist married to a JP Morgan executive. “The mayor runs it like a fiefdom.”

The mayor’s loyalists insist everyone is playing by the same lenient election rule book, and they blame newcomers for not respecting village traditions. “These new people are awful,” says Esther Hunt, 93, whose grandfather — a wool-industry magnate — first built a house in the village in 1913. Hunt is appalled by the newcomers “doing things that are very un-village,” like listing guest rooms on Airbnb.

The conflict has made bitter cynics out of some wealthy and otherwise sanguine liberals, and it promises to cast a pall on another year of dinner parties and sunset strolls and summering on top of one’s enemies.


Shelter Island was originally used by Europeans as a slave plantation in the 17th century. Some investors from Massachusetts settled the northern peninsula, now the site of Dering Harbor, as a summer resort in the 1870s. In 1916, around the time the hotel and golf club went bankrupt, the investors banded together and formed the village government, so they could transfer their land to the public trust in order to get out of bankruptcy. But after the village had auctioned off most of the land, it didn’t disband.

Now, almost a century later, in exchange for exorbitant property taxes, village residents get access to an independent water supply, twice-weekly trash pickup, and zoning and architecture boards that can tend toward draconianism. It’s a consummate example of why Governor Andrew Cuomo has decried the inefficiency of tiny municipalities and has set up a fund to help them dissolve themselves. In the case of Dering Harbor, this would mean joining the town government that oversees the rest of Shelter Island, population 2,392. But it surprises no one that the village — known as “Sneering Harbor” to others on the island — hasn’t taken Cuomo’s offer.

Tim Hogue took office as mayor around 1990. The New York Times described him in 1994 as a financial consultant, and the word around Dering Harbor is that he now works as a debt collector in the medical industry. (The village does not pay him a salary.) He rebuffed New York’s attempts to reach him for an interview, including phone calls, emails, and a note left at his doorstep. Besides Hogue, the village government consists of a four-member trustee board, which tends to back him on every measure. Like the mayor, trustees go up for reelection every other year, but their terms are staggered, so every summer there’s some kind of election.

The current battle lines between residents date back to 1991, when Martha Baker (then New York’s fashion editor) and her photographer husband moved into an abandoned Tudor on the island shore. Baker dug a lavish garden and put up a picket fence. She was told that since she didn’t have a permit, she’d be fined $200 a day if she didn’t tear the amenities down. “Page Six” caught wind and published a short story on the quarrel. Under the headline “Give ’em shelter from the neighbors,” it recounted how the “stylish couple” had been persecuted by the village’s “old guard.” Baker’s then-husband antagonized the neighbors further by mocking them in letters to the editor of the local paper. “And so then they really went to war,” Baker recalls. Her friends from the Shelter Island Yacht Club turned against her. Once their fence and garden issues were resolved, it took seven years, and a ruling from the New York Supreme Court, for Baker to get a permit for a veranda — even as her neighbors were securing permits with no trouble.

Baker and the other newcomers point out that the village has no distinct visual pattern, in the manner of Nantucket or Martha’s Vineyard. The architectural styles range from Greek Revival to Spanish Mediterranean to California Craftsman. “There is no Dering Harbor look!” says Bill Unger, a California venture capitalist and Baker’s companion. “They don’t have any fucking rules on any of this stuff. They’re just bad, nasty, mean-spirited people.”

The real-estate boom of the early 2000s brought an influx of newcomers from the city. Some say they sailed through the permit process as they remodeled their homes; others had debacles with permits. It was around 2010 that Alfredo Paredes — the chief creative officer of Ralph Lauren — and his husband, Brad Goldfarb, an editor at Architectural Digest, were looking to trade their place in the Hamptons for a new vacation home somewhere quieter. Goldfarb remembers the first time Paredes drove him through the village. “We saw these old Victorian houses,” Goldfarb says. “It looks like you’ve gone back in time. It seemed much more like the ideal of summer.”

They found a “Victorian pastiche” from roughly 1870, which they could “miraculously, just barely afford.” It had fallen into disrepair, so Paredes and Goldfarb restored it bit by bit. At first they were welcomed warmly: Neighbors brought them gift baskets and invited them to the annual Dering Harbor cocktail party. But the problems started when they wanted to put a hedge around their yard. There was a dispute about whether they owned the last 30 feet of grass around the perimeter, and Hogue told them that, until it was resolved, a hedge was out of the question.

The trouble was, they also heard gossip that neighbors didn’t like it when their weekend guests came to sunbathe by the water, and without a hedge they had no privacy. “I’m not going to tell my friends how small or large their bathing suit needs to be,” Goldfarb says. “And some of our friends are running around in their Speedos.” No neighbors have ever made explicitly homophobic remarks, but Goldfarb and Paredes have wondered if it’s in the background of their disputes. It doesn’t help that their house is situated on what Goldfarb calls the “50-yard line of the village,” directly between Hogue himself and one of his most loyal supporters, an 81-year-old widow whose late husband made a fortune in real estate.

So they put the hedge issue aside while they made other improvements to the house, but ultimately they filed a lawsuit to resolve the property-line issue. “Then the skies opened,” Goldfarb says, “and hell rained down.” A case in point: When they tried to spruce up their driveway, freshening the gravel and replacing the concrete curbs with brick, the village issued stop-work orders, and their landscaper received a scolding letter from their village attorney.


The dissension ultimately spilled over into the polling place. In 2013, Deybis Rodriguez, a banker and sometime New Jersey resident who said she lived in the village part-time at her partner’s vacation home, tried to vote in the election of two trustees. But her ballot was confiscated by the village clerk before she could even put it in the box. Hogue later dodged questions about it at a village meeting and from the Shelter Island newspaper.

The following year, when the mayor was up for reelection, he had a challenger for the first time in more than a decade: Patrick Parcells, a retired Wall Street banker who had bought his village property in 2001. Parcells’s backers dubbed themselves the Porch Party. He won 26–25 — but then had his victory annulled because one supporter had failed to sign her ballot envelope. A runoff election was planned.

During the month that followed, the voter roll swelled. At least one person (Bill Unger) who was dating a village resident and living in California admits he switched his registration just so he could vote for Parcells. But the Porch Party’s efforts were outstripped by those of Hogue’s supporters; the incumbent won the runoff 43–29.

In recent interviews on the island, some of Hogue’s supporters were forthright about enlisting relatives from outside the village to help tilt the result. In their defense, they said the other side started it — Rodriguez, whose residency in the village was dubious — and said it was sneaky for Parcells to run as a write-in candidate, announcing his bid via email shortly before the election.

To be fair, voter eligibility is a bit murky, according to state law. Eligibility to vote in a town requires having a “fixed, permanent, and principal home” there, which, by its strictest definition, calls into question the status of even many people who own houses in Dering Harbor, since they spend more of their time in New York City. However, a handbook issued by the New York Conference of Mayors & Municipal Officials says that residency is “primarily a matter of intent that is determined by a person’s conduct and by all other surrounding circumstances.” Dering Harbor’s Manhattanites reason, plausibly, that the line should be drawn at whether the person owns a home there at all.

The New York attorney general’s office, which oversees local elections, declined to comment. However, the state has never received any formal complaints about the village’s elections, and ordinarily state law does not require any independent election monitoring.

So will this month’s election reprise all the drama and dirty tricks? Probably not. The 2014 election sapped the insurgents’ fervor; so far no one has announced a campaign against Hogue. But two residents loosely associated with the Porch Party are running for trustee positions, against incumbents appointed by Hogue. Paredes said that, if anything, he expects even more nonresidents to vote this time around, because he believes the Establishment won’t be taking any chances.

Of course, these concerns — echoed by many of his neighbors — are based only on speculation and hearsay. It’s hard to know whether stricter scrutiny there would actually make any difference, or whether Hogue truly owes his authority to voter fraud, or even if he does, what any of this has to do with anyone’s hedges or Speedos.

What does seem clear is that the autocracy can’t last forever. The flow of Manhattanites has been a constant for the last two decades, and in the long run they’ll reach a critical mass of residents demanding big-city standards of government accountability and formality.

And in the meantime, the squabbles continue. As Goldfarb and Paredes’s lawsuit has been inching its way through the court system, they recently caught hell for replacing some shrubs on their property line with holly trees, which the village says constitute a living fence — something that requires a permit. “It’s created an uproar,” Goldfarb says. “So that could well end up in the courts also.”

Town of 11 People in Political Crisis