In 1639, a British military engineer named Lion Gardner purchased an island off the eastern tip of Long Island from the Montakeet Chief Wine Danch. The price was a large black dog, some Dutch blankets, powder, and shot. In 2025, a hedge fund manager paid $115 million for 8.5 acres on [music] Further Lane, roughly $13.
5 million per acre of sand and scrub grass. But the land had not changed. What changed is who wants it and what they’re willing to pay to claim they belong there. In today’s episode of Old Money Empires, [music] we trace four centuries of transformation on the eastern tip of Long Island. From Puritan settlement to Whailingport to Gilded Age summer colony to the most expensive real estate in the Western Hemisphere.
The story involves Nazi spies, a bludgeoned millionaire, a decaying mansion filled with 52 cats, and a family that has held the same island since before America existed. You see, the Hampton’s has always been contested ground. The price of entry simply keeps rising. Every Memorial Day weekend, the Long Island Expressway transforms into a parking lot of Range Rovers, Teslas, and Chauffeur Escalades inching toward the South Fork.
By Friday afternoon, helicopters ferry those unwilling to endure the traffic directly to private helellipads on oceanfront estates. See, the modern Hampton’s operates on a financial scale that would have astonished even the guilded age families who first built summer cottages there. For example, in 2014, hedge fund manager Barry Rosenstein paid $147 million for three contiguous oceanfront parcels on Further Lane in East Hampton.
In 2021, the Jewel Pond estate in water mill sold for $15 million. And in 2025, the former Terry Seml estate set the all-time record $115 million for eight and a half acres, approximately $13.5 million per acre of oceanfront property. The median Hampton’s home price now exceeds $2 million. In Saga Panic, the median reaches $7.4 million.
Yet, the true old money of the Hampton’s regards all of this with aristocratic indifference. The Gardener family has held Gardener’s Island continuously since 1639, 386 years of unbroken ownership, the longest in American history. Robert David Lion Gardener, the 16th Lord of the Manor, who died in 2004, embodied the distinction between authentic lineage and mere wealth. When a Mrs.
Dupont admired his grandfather clock and asked where he got it, Gardner replied, “We didn’t get it. We had it made.” The clock had been crafted for a gardener ancestor from the Dominy brothers in the 18th century. On the subject of other wealthy families, Gardener was equally dismissive. As for the Dupants, Rockefellers, and Fords, they are nuvoish. The Dupants came in 1800.
They’re not even a colonial family. The tangled dynamics between Old Hampton’s lineage and New Hampton’s money fill our free Substack newsletter, where the social machinery beneath the hedros proves considerably more interesting than the real estate listings suggest. You can access that by visiting the first link in the video description.
Now, the gardeners represent the apex of the Hampton’s machinery. Their island at 3,318 acres remains one of the largest privatelyowned islands in the United States. Estimated value exceeds several hundred million. Annual upkeep runs approximately 2 million before accounting for historic preservation and shoreline erosion.
The family nearly lost it during the Great Depression when the island went up for sale in 1937 due to prohibitive costs. A relative, Sarah Diodati Gardner, purchased it for $400,000, keeping it in family hands. Subsequent generations fought bitter litigation over ownership and direction for 22 years. Today, Alexandra Creo Gollet owns the island unilaterally under conservation easement.
Pre-revolutionary lineage creates a hierarchy invisible to outsiders, but keenly felt within the Hampton social structure. Colonial gentry rank above guilded age industrialists who rank above Wall Street finance who rank above hedge fund billions. So the founding families may no longer dominate wealth but they retain something money cannot purchase and that hierarchy began taking shape nearly four centuries ago.
The Shinak and Montakeet were agonent speaking peoples who had occupied eastern Long Island for thousands of years before English contact. By 1640, when the English settlers arrived, the Shinikok controlled lands around present-day Southampton, while the Montakeid held the eastern tip around what became East Hampton and Maque.
They were maritime peoples, fishing, clamming, whailing from the shore, cultivating corn and beans with sophisticated political structures led by hereditary sichchums. The 1640 Southampton deed gave Shinikok Sichchums including Mandush 16 coats and 60 barrels of trade goods for the land that became the town.
The 1648 East Hampton purchase 31,000 acres of Montakeet territory cost the English 30 shillings and 8 p in goods. 20 coats, [music] 24 mirrors, 24 hatchets, 24 knives and 100 small metal drills called mukes for making wampam. The swindle was conceptual rather than numerical. English settlers understood these transactions as permanent property transfers.
Deeds granting ownership to have and to hold forever. The sichums operating within an algangquin framework of communal land use almost certainly understood them as gift exchanges establishing reciprocal obligations and shared use rights. Lion Gardner systematized this by crowning wand grand sichchum of all Long Island, a wholly fictitious title that allowed Gardner and his associates to purchase land across the island from a single compliant source. Historian John E.
Strong argues the Montakeet’s lack of military power made a mockery of this presumptuous title, enabling Gardner to avoid the difficulties of negotiating with the [music] numerous small bands living on the islands in question. Gardner’s relationship with Wan Danch was both genuine friendship and calculated alliance.
In 1637, 3 days after English forces massacred nearly 700 Peekquats at Mystic, Wand visited Gardner to ask if the English were angry with all Indians. Gardner demanded Wand bring him the heads of any Peekquats who came to Long Island. Wand complied. Gardner paid for the five heads delivered. This brutal compact spared eastern Long Island the decades of warfare that plagued New England and positioned both men to control land transactions [music] for over the next two decades.
On June 12th, 1640, approximately 40 Puritan families landed at a slender beach and now what is Noyak Bay, a spot they named Conscience Point after one settler reportedly exclaimed, “For conscience sake, we’re on dry land.” Southampton, like East Hampton, founded eight years later, functioned as a Puritan Bible Commonwealth, a semi-autonomous town, meaning democracy that restricted full citizenship to co-religionists, but pioneered self-government.
So distant were the eastern towns from centers of power, that historian Nathaniel S. Prime wrote that they were absolutely in a state of nature, possessing all the personal rights and privileges which the god of nature gave them, but without the semblance of authority over one another. Wy and Danch died in 1659, possibly poisoned.
Gardner mourned him as my friend and my brother. For the next two centuries, the descendants of both men would share the same windswept landscape. One group holding deeds, the other holding memories of what the deeds had cost them. Then the whales arrived, and everything changed. For most of the 18th and 19th centuries, the Hamptons was not a playground, but an economic engine.
Sag Harbor’s railing industry began modestly in the 1760s and exploded after the American Revolution. In 1789, when President Washington approved Sag Harbor as a port of entry, established one day before New York City, the village had more tonnage of square rigged vessels engaged in commerce than the city itself. The industry peaked in 1845 with a fleet of 63 or 64 vessels.
At its height, Sag Harbor was second only to New York City in maritime importance on the east coast. A global hub where warves were lined six ships deep and the streets were teamed with carpenters, culkers, sail makers, riggers, blacksmiths, coopers, and sailors from around the world. Ships returned from voyages lasting 2 to four years to the Pacific, waters off Japan, Hawaii, New Zealand, and the Arctic Circle carrying 2,00 to 2500 barrels of oil each.
Jedodiah Conklin, a blacksmith who stamped each harpoon with his makaker mark, Jay Conklin, employed 12 men in his shop at the industry’s peak. The fortunes built on whale oil did not translate into guilded age dynasties. However, in 1845, a catastrophic fire destroyed 95 buildings in Sag Harbor, wiping out critical infrastructure just as profit margins began shrinking.
By the 1850s, with the Atlantic fished out, kerosene replacing whale oil, and the California gold rush draining manpower, the fleet shrank from 64 vessels to just 24. Sag Harbor’s last whaler, the Brig Myra, sailed in 1871 and was condemned as too leaky to return home. One local resident described the aftermath as Dozeville.
Wars rotted, boat shops closed, and streets that once roared with life fell silent. The American Revolution had already tested the region’s capacity for hardship. The Battle of Long Island in 1876 was catastrophic for Washington’s army, and by September, all of Long Island fell under British occupation lasting until 1783.
Many patriots fled to Connecticut, leaving behind women, the elderly, and children. Those who remained faced plundered crops, commandeered homes, and enforced English law. Some signed oaths of allegiance to the crown documented in Trian’s list of November 1778. A pragmatic survival strategy that later brought accusations of disloyalty and punitive taxes.
Yet isolation established a pattern. The Hamptons as refuge from crisis, a place to which people fled when centers of power became unbearable. The Monta Point Lighthouse, authorized by President Washington in 1792 and completed in 1796 at a cost of $20,000 marked the Young Nation’s easternmost assertion of authority.
At 110 ft tall, it was the first lighthouse built in New York State and remains the fourth oldest continuously operating lighthouse in the nation. The whaling industry was dead by 1871, [music] but salvation was already steaming toward them on iron rails. In 1870, direct railroad service reached Sag Harbor, and the eastern tip of Long Island began its pivot from working port to summer destination.
The Long Island Railroad extended to East Hampton in 1895, cutting travel time from Manhattan to under 3 hours and opening the South Fork to wealthy New Yorkers seeking escape from the city’s summer heat, noise, and disease. Within a generation, potato fields became estate grounds. Now, the transformation was deliberate. In 1891, members of the local summer colony, many from long-established New York Protestant families, founded Maidstone Club in East Hampton.
The club was explicitly designed to consolidate the old family summer colony into a semi-private enclave, organizing tennis, social life, and later golf for what members considered the right sort of people. Admission was primarily about family background and personal reputation rather than explicit written criteria.
By the 1920s, after a move to its current oceanfront location and construction of its now famous Lynx courses, Maidstone functioned as a semi-closed registry of old East Hampton names, belonging to Maidstone essentially defined the upper tier of the social map. Journalists writing in the 1990s and 2000s, consistently described its membership as second and third generation Hampton’s Wasp families, often with inherited houses nearby, reinforcing a club village ecosystem that determined who mattered.
The Gilded Age summer colony built houses to match their social ambitions. Along the ocean in Southampton and East Hampton, families constructed sprawling shingle-style cottages with wraparound porches, servants quarters, and manicured grounds stretching to the dunes. These were not the Baroque palaces of Newport.
The Hampton style was more restrained, emphasizing connection to landscape rather than domination of it. But they were unmistakably statements of arrival and belonging. The founding families who had held land since the 1600s watched this invasion with mixed feelings. The newcomers brought money, infrastructure, and employment.
And they also brought different values, different social structures, and a different relationship to the land. For the colonials, land was heritage. For the guilded age arrivals, it was amenity. Railroad developer Austin Corbin and his associate Arthur Benson represented this new attitude most aggressively. In the 1890s, they used deceptive pressure tactics to get Montalkets to surrender rights to their ancestral lands for Corbin’s proposed Manhattan to Monta Dewater port rail line.
When the Montalkets sued in 1900, Benson’s lawyers argued that intermarriage had diluted their Indian blood. In 1910, Judge Abel Blackmar ruled that the Montalkets had disintegrated and no longer existed as a tribe. The decision was widely viewed as racist, but it was upheld anyway. Developer Carl Fiser later envisioned Montalk as the Miami Beach of the North, sparking construction that was undone by the Great Depression.
The crash of 1929 slowed the transformation. Then in September 1938, nature intervened with a force that no amount of money could stop. On the afternoon of September 21st, 1938, a category 3 hurricane made landfall on Long Island’s Southshore with sustained winds around 120 mph. The storm killed approximately 700 people across the region and caused property losses of $36 million, equivalent to nearly 7 billion in current value.
The Hamptons bore the brunt. In West Hampton Beach, approximately 30 people died, the highest death toll of any Hampton’s community and 179 beach homes lining Dune Road were destroyed, leaving only two structures standing. Both were uninhabitable. West Hampton Beach Mayor Conrad Teller, who was in fourth grade that year, recalled his father, then police chief, describing the waves.
He saw the first wave come over, and it wasn’t that great. He said the second wave went over the telephone poles. The storm surge turned Montalk into a temporary island, flooding across the South Fork and obliterating the Long Island Railroad tracks. At Maidstone Club, surge washed over the clubhouse and flooded the golf course.
The hurricane carved seven new inlets between Moritius Inlet and Quag, permanently redrawing the map at Shinikok. Years of lobbying for an inlet were rendered moot when the surge simply cut a wide passage in a few hours. But the destruction paradoxically enabled transformation. The early 20th century cottage colonies on the barrier beaches were effectively erased, leaving ownerless or heavily damaged plots.
When postWorld War II prosperity brought new wealthy buyers, they built not on ruins, but behind them larger estates, higher elevations, more robust construction. The hurricane had written off the early guilded age beachfront as too risky for all, but those wealthy enough to spend millions on seaw walls and flood insurance.
4 years after the hurricane, global warfare reached the Hampton’s beach. On the foggy night of June 13th, 1942, German submarine U22 surfaced off Amiganset. Four Nazi sabaturs in full German Marine infantry uniforms rode ashore in a rubber raft carrying four wooden crates of explosives, forged identity papers, and $175,200 in genuine American currency.
Their targets included aluminum plants, railroad bridges, New York City’s water supply, and hydroelect electric plants at Niagara Falls. At approximately 12:15 in the morning, 21-year-old Coast Guard seaman John Cullen encountered the men during a routine patrol. Unarmed except for a flare gun, Cullen sensed danger immediately when one sabotur claimed they were fishermen with clams in the bag.
No local would dream of clamming in the surf at night. The lead sabatur stuffed $300 into Cullen’s hand and asked repeatedly, “Would you recognize me if you saw me again?” Cullen took the money and sprinted back to the Coast Guard station. Within 14 days, all eight sabatururs were in custody. Six were executed by electric chair on August 8th, 1942.
The war ended, the soldiers went home, and a different kind of invasion began. In November 1945, Jackson Pollock and his wife Lee Kraner purchased a farmhouse with a barn in Springs for $5,000. affordable on Peggy Guggenheim’s $300 monthly stipend. And this move transformed American art. In that barn, Pollock positioned canvases on the wide wooden floor and developed his revolutionary drip technique.
The couple became central to transforming springs from rural hamlet to artist colony. They were very sociable, hosting numerous house guests from New York. Many visitors ended up buying or renovating in the area. And pretty soon, the Springs really became the art colony rather than East Hampton Village. By the early 1950s, Springs housed an extraordinary concentration of abstract expressionist talent.
Will Ela Duning, James Brooks, Charlotte Park, and John Little. What attracted them was the quality of light, the affordability, and the solitude. What ended it was success. On August 11th, 1956, Pollock posed for a photograph on his springs estate with his mistress, Ruth Clickman. Hours later, he was dead.
Late that evening, Pollock drove his green 1950 Oldsmobile convertible with Clickman and her friend Edith Meer. All three had spent the day drinking. “You want to go to this party?” Pollock shouted. “How about this?” He floored the accelerator to 60, then 70, then 80 mph. On a curb less than a mile from home, Pollock lost control.
The car skidded into the woods, bounced off a tree, and then rolled. Pollock died instantly. The car rolled over Mezer, breaking her neck. Cliggman was thrown free and survived. Now, a 1965 New York Times article noted that artists follow sun to the Hamptons and followers follow artists, describing how Pollock and his friends once lived there in seclusion, but the area had transformed.
Another symbol of the transition lived on Middle Lane in East Hampton. Big Edie and Little Edie Bruvier Beal, aunt and first cousin of Jacqueline Kennedy Onasses, occupied Grey Gardens, a 14- room mansion designed in 1897. By the early 1970s, the house had become something else entirely. In October 1971, Suffach County Health Department officials descended with a search warrant.
They found an estimated 52 cats, over 200 bags of cat waste in the basement, no running water or functional heat, and walls so rotted they would move out 12 in when touched. A grand piano had collapsed through the floor. The officials declared the home unfit for human habitation. Jackie Kennedy quietly provided $25,000 for cleanup.
Enough to satisfy inspectors, not enough to truly restore the property. When little Edy finally sold Grey Gardens in 1979, she accepted $220,000 from Washington Post editor Ben Bradley. In 2017, the restored property listed for nearly $20 million. Grey Gardens captured authentic Hampton’s eccentricity at the exact moment such lifestyles were being displaced.
The Bohemian era had produced artists who couldn’t afford rent and aristocrats who couldn’t afford repairs. The next era would produce something else entirely. A murder victim worth $80 million killed by a man who installed his security system. The 1980s transformed the Hamptons from artist refuge to celebrity playground. The Reagan era economic surge spawned a generation of newly [music] wealthy and the Hamptons endowed with natural beauty and conveniently situated near Manhattan became inundated.
Steven Spielberg, Calvin Klein, Jerry Seinfeld, and Jackie Kennedy Onasses maintained residences. The area earned the nickname Hollywood East, and the Maidstone Club consolidated its role as social gatekeeper. The club had excluded Jews until the late 1970s. Groucho Marks, Jewish, rich, and world famous, could appear as a guest in the 1950s, but was turned down for membership.
As late as the 1990s, there were reportedly no black members. Diana Ross, then married to shipping and magnate Arie Ness Jr., was reportedly denied membership, prompting Ness to resign. The working families who had lived there for centuries, found themselves squeezed out. The Bonikers, descendants of English settlers, arrived in the 1640s, had formed a tight bayon culture of clammers, fishermen, and potato farmers for 350 years.
A local writer described them as having thrived from 1640 until about 1990 and noted that by the time he wrote, “They’re mostly gone.” Exploding property values meant Boniker houses suddenly appeared on tax roles as million-doll assets even when owner’s incomes had not changed. Families who had held Bayfront land for generations found annual taxes exceeding their working incomes.
They sold to developers and moved inland. The concentration of extreme wealth created new vulnerabilities. On October 22nd, 2001, Ted Aemon, a former KKR executive worth between 40 and $80 million, was found bludgeoned to death in the master bedroom of his East Hampton estate. East Hampton had not seen a murder in over 20 years.
Ammon was in the midst of a bitter divorce from his wife Jenner Rosa who had begun an affair with Daniel Pelosi, a married electrician who had installed the very security system meant to protect against intrusion. The system had been disabled. The hard drive was missing. Pelosi was convicted in 2004 and sentenced to 25 years to life.
Then CO 19 completed the transformation. The 2020 exodus from Manhattan sent rental prices surging and average sale prices to $2.35 million, up 24% from the previous year. By 2025, median prices exceed $2 million and trophy properties routinely clear 100 million. Thus, the ark is complete. Land purchased for 10 coats of trading cloth now sells for $13.5 million per acre.
A family that bought their island for a large black dog still holds it after 386 years while dismissing Rockefellers as Nuvo Ree. The Hamptons has always been about who gets to claim they belong. The currency of belonging has simply changed from lineage to liquidity, from coats to capital, from Wyan Dench’s handshake to hedge fund wire transfers.
And the price keeps rising. And now we’d love to see you in the comments. Have you ever spent time in the Hamptons? And if so, do you love it or hate it? We can’t wait to hear from you. I grew up going to Sag Harbor quite a bit, so this means a little bit to me. And I look forward to seeing you on the next episode.
Thanks for joining us at Old Money Empires.
