John B. Fairchild and the Legacy of the Real Men Who Bought Fire Island

John B. Fairchild and the Legacy of the Real Men Who Bought Fire Island

Fire Island isn't just a sandbar off Long Island. It’s a myth. For decades, people have argued over who "owns" it, who "built" it, and who the man who bought Fire Island actually was. Honestly, it depends on which part of the island you’re standing on and which decade you're talking about. If you're looking for one name, you’re usually looking for John B. Fairchild or perhaps the developers like the Cherry Grove pioneers, but the reality is way more fragmented and interesting than a single real estate transaction.

You've probably heard the rumors. People talk about a single visionary buying the whole thing for a pittance. That's mostly a fairy tale. Fire Island is a patchwork of seventeen different communities, each with its own "founder" and its own vibe.

The Myth of the Single Owner

Let's clear something up right away. Nobody "bought" the entire island in one go like a Bond villain. In the late 19th century, much of the land was considered worthless. It was basically a giant, shifting dune. The Benedict family held huge swaths of it early on, specifically the area that became Cherry Grove. They bought it in the 1800s. Back then, they weren't looking to build a cultural mecca; they were looking for salt hay and maybe some fishing access.

But if you’re asking about the man who bought Fire Island in the sense of making it what it is today—the fashion-forward, high-society, queer-friendly sanctuary—you have to talk about John B. Fairchild.

Fairchild was the publisher of Women’s Wear Daily (WWD). In the 1960s, he didn't just buy property; he bought into the lifestyle of the Pines. He saw what was happening in this isolated, car-free paradise and decided it was the center of the universe. He used his massive media influence to turn a remote beach into the "it" spot for the global elite.

Why the Pines Became the Epicenter

The Pines started because of a man named Home W. Nichols. In 1952, he began developing the area. It wasn't an easy sell. You had to haul everything in by boat. There were no roads. There are still no roads. But the isolation was the point.

When the original farmhouse in Cherry Grove burned down in 1915, it cleared the way for a different kind of development. But it was the post-WWII era where the "buying" really got intense. Developers like the Lawrence family and the Sayville Ferry Service owners realized that if they controlled the transport, they controlled the island.

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John B. Fairchild: The Man Who Sold the Island to the World

Fairchild is the name that pops up most in business circles. He was a force of nature. He’d arrive at the Pines and suddenly, the biggest designers in the world—Halston, Calvin Klein, Bill Blass—were all there too. He didn't just buy a house; he bought the narrative.

Think about this: In the 60s and 70s, the Pines was a place where you could be anyone. Fairchild captured that. He wrote about the parties. He wrote about the "In Crowd." He turned the "man who bought Fire Island" trope into a reality by making the real estate so valuable that only the ultra-wealthy could touch it.

But he had competition for the title.

The Developer Who Actually Built the Pines

If we're talking about the physical act of buying and building, we have to mention Peggy Fears. She was a Broadway star who bought property in Cherry Grove and built the Beach Hotel in the 1940s. She was instrumental in making the island a haven for the LGBTQ+ community long before it was socially acceptable elsewhere.

Then there’s Bob Guccione, the founder of Penthouse. He famously bought property there and tried to exert influence. It didn't always go well. The island has a way of spitting out people who try to "own" it too aggressively.

The Geography of Ownership

Fire Island is 32 miles long. It's skinny. Sometimes only a few hundred yards wide. Because of this, "buying the island" usually meant buying a specific tract.

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  • Cherry Grove: The oldest settlement. Bought by the Benedicts, then developed by locals.
  • The Pines: Developed later, specifically targeting a high-end, aesthetic-driven crowd.
  • Ocean Beach: The "metropolis" of the island, with its own distinct governing body and very different ownership history.

It’s kinda wild when you think about it. You have this fragile ecosystem that is constantly being eroded by the Atlantic, yet the land value is astronomical. The "man who bought Fire Island" today is likely a private equity giant or a tech billionaire hiding behind an LLC.

The Modern Reality: Who Owns it Now?

Today, the "owner" is increasingly the National Park Service. In 1964, the Fire Island National Seashore was established. This was a direct response to Robert Moses—the "Master Builder" of New York—who wanted to build a massive highway right down the middle of the island.

Moses is the man who tried to buy Fire Island’s future. He wanted to pave it. He wanted to connect it to the mainland with a road that would have destroyed the very thing that makes it special. The residents fought back. They used their political connections—people like Fairchild and other wealthy homeowners—to stop him.

The creation of the National Seashore meant that, in a way, the American public "bought" Fire Island. It halted major development and preserved the 17 private communities as enclaves within the park.

Misconceptions About the Sale

People often confuse Fire Island with other private islands. You’ll hear stories about it being traded for a trunk of beads or a few bottles of rum. While there were certainly questionable deals with the indigenous Unkechaug people in the 1600s, the modern "buying" of the island was a slow, litigious process of land grants and sub-divisions.

One big mistake people make is thinking the island is one big private club. It’s not. It’s a complex web of:

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  1. Private residential lots.
  2. Commercial zones (very small).
  3. Federal land.
  4. State parks (Robert Moses State Park on the west end).

Why This History Matters for Travelers and Investors

If you’re looking at Fire Island today, you aren't just looking at real estate. You’re looking at a legacy of defiance. The people who bought into this island—from the 19th-century fishermen to the 20th-century fashion moguls—were buying an escape.

The "man who bought Fire Island" wasn't one person. He was a series of people who realized that a place without cars, where you have to walk on wooden boardwalks and carry your groceries in a red wagon, was more valuable than a skyscraper in Manhattan.

How to Navigate Fire Island Today

If you're planning to visit or looking into the history for research, keep these things in mind:

  • The Ferry is King: You don't drive there. You take a ferry from Bay Shore, Sayville, or Patchogue. The people who own the ferries basically run the access to the island.
  • Communities are Distinct: Don't go to Ocean Beach expecting the party vibe of the Pines. Don't go to the Pines expecting the family-centric quiet of Fair Harbor.
  • The Environment Rules: No matter who "buys" a house, the ocean is the ultimate landlord. Erosion is a constant threat.

Actionable Steps for the Fire Island Enthusiast

If you want to truly understand the "man who bought Fire Island" narrative, you need to see the remnants of their visions.

  1. Visit the Carrington House: Located between Cherry Grove and the Pines, this is where Truman Capote famously worked on Breakfast at Tiffany's. It’s a prime example of the kind of "buying" that mattered—buying space for creativity.
  2. Research the 1964 National Seashore Act: This is the most important "purchase" in the island's history. It explains why the island isn't covered in high-rise condos today.
  3. Check the Long Island Museum Archives: If you're a history buff, look up the Tangier Smith land grants. That’s where the legal paper trail for most of these "purchases" actually begins, dating back to the 1600s.
  4. Explore the Pines via the Boardwalks: To understand John B. Fairchild's influence, walk through the "Co-ops" and the high-design houses. You'll see how his aesthetic sense still dominates the architecture of the area.

Ownership on Fire Island is temporary. The sand shifts. The boardwalks rot and get replaced. The "man who bought Fire Island" is really just a person who realized they could rent a piece of paradise for a little while before the tide comes back in.