The Hamptons: "Old Money" To Ultra Rich

This episode covers how the Hamptons transformed from Puritan settlement and whaling port to Gilded Age colony and ultra-rich real estate market, including the Gardiner family's 386-year island ownership, Nazi saboteurs landing in 1942, Jackson Pollock's Springs art colony, Grey Gardens decay, and modern oceanfront prices reaching $13.5 million per acre.

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TIMESTAMPS:
0:00 Introduction
1:11 Chapter One: Thirteen Million Dollars Per Acre
4:52 Chapter Two: Ten Coats of Trading Cloth
8:31 Chapter Three: When the Hamptons Was a Working Port
11:48 Chapter Four: The Gilded Age Arrives
15:09 Chapter Five: The Hurricane and the Saboteurs
18:29 Chapter Six: The Artists and the Decay
22:04 Chapter Seven: Blood, Money, and the Price of Belonging

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Lion Gardiner purchased Gardiners Island in 1639 from Montaukett chief Wyandanch for a large black dog, some Dutch blankets, powder, and shot, establishing the longest continuous family ownership in American history at 386 years.

In 2025 a hedge fund manager paid $115 million for 8.5 acres on Further Lane—approximately $13.5 million per acre of oceanfront property in East Hampton.

The 1640 Southampton deed gave Shinnecock sachems including Mandush sixteen coats and sixty bushels of trade goods, while the 1648 East Hampton purchase of 31,000 acres cost thirty pounds four shillings and eightpence in goods.

Sag Harbor's whaling industry peaked in 1845 with a fleet of 63-64 vessels, making it second only to New York City in maritime importance on the East Coast with ships returning from Pacific voyages carrying 2,000-2,500 barrels of oil each.

An 1845 catastrophic fire destroyed 95 buildings in Sag Harbor, wiping out critical infrastructure just as profit margins began shrinking, and the last whaler—the brig Myra—sailed in 1871.

Direct railroad service reached Sag Harbor in 1870, with the Long Island Rail Road extending to East Hampton in 1895, cutting travel time from Manhattan to under three hours.

Maidstone Club was founded in 1891 by members of the local summer colony—primarily long-established New York Protestant families—designed to consolidate the old-family summer colony into a semi-private enclave.

On September 21, 1938 a Category Three hurricane made landfall with sustained winds around 120 mph, killing approximately 700 people across the region and destroying 179 beach homes in Westhampton Beach.

On the foggy night of June 13, 1942 German submarine U-202 surfaced off Amagansett, with four Nazi saboteurs rowing ashore carrying explosives, forged papers, and $175,200 in genuine American currency.

Coast Guard Seaman John Cullen encountered the saboteurs at 12:15 AM, and within fourteen days all eight were in custody with six executed by electric chair on August 8, 1942.

In November 1945 Jackson Pollock and Lee Krasner purchased a farmhouse with barn in Springs for $5,000 on Peggy Guggenheim's $300 monthly stipend, transforming the area into an Abstract Expressionist art colony.

On August 11, 1956 Pollock drove his 1950 Oldsmobile convertible with passengers Ruth Kligman and Edith Metzger, losing control at 80 mph on a curve less than a mile from home, killing himself and Metzger instantly.

Big Edie and Little Edie Bouvier Beale—aunt and first cousin of Jacqueline Kennedy Onassis—occupied Grey Gardens until October 1971 when health officials found an estimated 52 cats, over 200 bags of cat waste, and walls so rotted they would "move out twelve inches" when touched.

Little Edie sold Grey Gardens in 1979 for $220,000 to Washington Post editor Ben Bradlee, and in 2017 the restored property listed for nearly $20 million.

On October 22, 2001 Ted Ammon—a former KKR executive worth $40-80 million—was found bludgeoned to death in his East Hampton estate, with electrician Daniel Pelosi convicted in 2004 and sentenced to 25 years to life.

Robert David Lion Gardiner, sixteenth Lord of the Manor who died in 2004, dismissed wealthy families as "nouveaux riches" stating "The DuPonts came in 1800; they're not even a colonial family."