The Gardiners: Tales From a Founding Family

1960s photo of the Winthrop Gardiner House at 95 Main Street, when it was known as the Gardiner Brown House. Photo by Eunice Juckett Meeker, from the East Hampton Library’s Long Island Collection

Like so many, Karl Grossman had peered at Gardiner’s Island — a privately owned oasis with 27 miles of coastline, forbidden without a proper invitation — from the coast of Napeague.

In the early 1970s, the journalist didn’t know it was home to Bostwick Forest, the largest stand of white oak in the American Northeast, or 1,000 acres of meadows, or New York State’s largest colony of ospreys, living among a swath of surviving, 17th-century wood-frame structures.

And he couldn’t have imagined that he would get a private tour from Robert David Lion Gardiner, who proclaimed himself the 16th Lord of the Manor, while making the 10-part documentary, “Can Suffolk Be Saved?”

“I’ve been on lots of islands off Long Island: Plum Island, Fishers Island, a little farther out, Cuttyhunk. But Gardiner’s Island really takes the island cake,” Grossman said. “There’s nothing like it. It’s essentially the way it was when Columbus landed. When we were filming, that’s when I got to know it, and saw how incredibly important it is, from an ecological point of view.”

It is ground he will cover during “Gardiner’s Island: America’s Oldest Family Estate,” as part of the Tom Twomey Lecture “The Gardiner Family Legacy: Two Iconic East Hampton Estates,” on Saturday at the East Hampton Library.

He will be joined by Chip Rae, who will discuss “95 Main Street: Winthrop Gardiner’s Remarkable Village Estate” — the meet-up location before Grossman and his film crew set off with Gardiner to tour his family’s 335-year-old legacy in 1974.

“Standing on Gardiner’s Island, it’s a wonderful, magnificent island, with fresh water ponds. It’s what all of Long Island once was,” Grossman said. “It’s delicate. It’s a breathtaking place, frankly.”

An aerial view of Gardiner’s Island.

The island’s recorded history dates back to 1639, when the original Lion Gardiner — red bearded and standing over 6 feet tall — bought the island from the Montaukett Indians for one large black dog, one gun, some powder and shot, some rum, and several blankets, all worth about five pounds sterling, Grossman said.

“The native people didn’t really understand the purchase of land. They didn’t believe you could own land,” Grossman said. “Land was like the sun and the ocean. I have a big question in my head whether they understood what was happening. Then, King Charles I got a charter for the island, saying that Lion Gardiner would have possession for all time of the island. That’s why it’s, historically, of importance.”

But there are other tales of note attached to the island, too. There’s Captain William Kidd, a pirate who, in the late 1600s, landed on the island to buy his treasure before turning himself in to clear his name. The Gardiners handed over the gold and jewelry, as they were ordered — all but one large diamond, or so the legend goes. Meanwhile, in London, Captain Kidd was convicted of murder and was hanged twice, because the rope broke the first time.

One of the more colorful Gardiner descendents was Julia, whose looks and charms earned her the title “the Rose of Long Island.” She was a heartbreaker, leaving English noblemen and an Italian prince in her wake before dating two congressmen and three Supreme Court justices stateside — all before age 30.

She would entrance President John Tyler, who was three decades her senior and an unsuitable match, according to Julia’s mother, because he was not wealthy enough for a Gardiner. It did not stop them from marrying, and for a time, the first lady of the United States was a native of Gardiner’s Island.

It is the last heir of the island who stands out to Grossman, he said, having interviewed him intermittently over the years. “I kind of knew him well,” he said. “He was quite a character. He spoke with almost a British accent, and was really quite the actor, and really considered himself, in a way, like royalty.”

He is quoted as telling American Heritage magazine, “We have always married into wealth. We’ve covered all our bets,” and “We were on both sides of the Revolution, and both sides of the Civil War. The Gardiner family always came out on top.”

“He also said, ‘As for the Du Ponts, Rockefellers, and Fords, they are nouveaux riches. The Du Ponts came in 1800; they’re not even a colonial family,’” Grossman said. “He loved to take people on his boat — he had this boat called The Jolly Roger, he had it moored on Three Mile Harbor — and he loved showing people the island. He really considered himself the Lord of the Manor.”

At age 93, Gardiner died in 2004 at home in East Hampton, and the town granted a conservation easement on the island until 2025. As to what will come next? That remains under speculation, Grossman said.

“If it would just be preserved, period, as a time capsule just the way it is, it would be of such environmental and historical importance,” he said. “I think the 95-percent conservation easement is great — and it’s wonderful that it was negotiated — and I don’t ever want to see the island trampled over. But if there’s somehow a way to preserve that island as a museum piece, as an environmental and historical museum piece, that’s what should be done.”

The Tom Twomey Series continues with “The Gardiner Family Legacy: Two Iconic East Hampton Estates,” featuring Karl Grossman, Chip Rae and Richard Barons, on Saturday, October 13, at 6 p.m. at the East Hampton Library, located at 159 Main Street in East Hampton. Admission is free. For more information, call (631) 324-0222 or visit