Chapter 1: Driftwood

Before the revolution. Before I arrived.

Anguilla didn’t look like the rest of the Caribbean. From the air, it barely looked like anything at all. A long, low strip of coral—thirty-five square miles of scrub and limestone—set in a sweep of blue that seemed too large for it. No mountains. No rivers. No deep harbors. Nothing that announced itself as valuable to the powers that had spent centuries dividing and exploiting the region.

Other islands declared their purpose immediately. You could see it from a distance: green rises of sugar land, windmills turning, ports deep enough for ships to anchor and remain. They had been shaped—sometimes brutally, always deliberately—into parts of an imperial system.

Anguilla resisted that shaping, not by design but by nature. The soil was thin, the rainfall unreliable, and the coastline offered few places where anything larger than a small boat could land easily. What couldn’t be readily exploited was often ignored, and what was ignored was left to develop on its own terms.

A man standing there in 1960 wouldn’t have called it neglect. It was simply the way things were. Anguilla had been bypassed for centuries.

The historical record reflects that neglect with a consistency that borders on indifference. Early accounts describe an island with little trade, little shipping, and little governance. Visitors remarked not only on poverty, but on isolation—an absence of connection to the larger currents shaping the Caribbean world. There were no plantations of consequence, no concentrated wealth, no infrastructure that tied Anguilla securely into the machinery of empire.

And yet those same accounts reveal something else: a people who endured.

They built lives in a place that offered almost no margin for error. They fished the surrounding waters, coaxed crops from thin soil, built boats, left when necessity demanded, and returned whenever they could. Over generations they fashioned a society organized not around plantations or overseers, but around families, small parcels of land, and a deeply rooted independence that didn’t require formal recognition to exist.

Hodge. Webster. Harrigan. Richardson. Adams. Gumbs. Rogers, Rey. Lloyd. These are only a few of the family names that came to define Anguilla.

They were never wealthy, but neither were they passive.

What outsiders often saw—what writers such as Naipaul would later dismiss as the “jetsam of an empire”—missed the essential truth. Jetsam is what is thrown overboard. It is what remains after something has been broken, stripped of purpose, discarded, and forgotten.

Anguilla was never that.

It wasn’t discarded. It was left alone. And those aren’t the same thing.

The modern world arrived unevenly.

There were glimpses of it. A modest telephone system connected parts of the island to one another and, in limited ways, to the outside world. Service was imperfect, but it represented something larger than convenience. It suggested that Anguilla, however slowly, might no longer remain beyond the reach of progress.

Then Hurricane Donna came.

It struck in September 1960 with devastating force. Roofs disappeared. Boats were driven ashore or out to sea. Trees that had stood for generations lay uprooted across the island. Roads vanished beneath debris. Families emerged from the storm to find familiar places suddenly unfamiliar.

Among what disappeared were the telephone lines.

Not damaged.

Gone.

In a single night, the fragile system that connected Anguilla to itself—and to the outside world—ceased to exist.

Storms pass. Damage can be repaired. That’s the expectation.

What made Donna different wasn’t the destruction.

It was what followed.

Or, more precisely, what didn’t.

The telephone system was never restored in any complete or meaningful way. Not quickly. Not systematically. Years passed. Anguillians adjusted, as they always had, but without expecting that what had been lost would be replaced.

Communication returned to word of mouth. News traveled by boat, by small aircraft, by travelers, by memory. The island adapted because it had no choice.

The storm itself faded into history.

The absence of rebuilding didn’t.

By then, Anguillians could see that rebuilding was possible.

They had only to look south.

Seven miles.

That was the distance to St. Martin.

Seven miles isn’t distance.

It’s contrast.