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 cut deep enough for ships to anchor and stay. 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 to land anything larger than a small boat without difficulty. What could not be easily used was often ignored, and what was ignored was left to develop—if that is the word—on its own terms.

A man standing there in 1960 would not have called it neglect. It was simply the way things were.

It had been bypassed. For centuries.

The historical record reflects that neglect with a kind of consistency that borders on indifference. Early accounts describe an island with little trade, little shipping, little governance. Visitors noted not just poverty, but 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 into the machinery of empire.

And yet those same accounts record something else: a population that endured. People who built lives in a place that offered very little margin for error. They fished, raised small crops where they could, built boats, left when they had to and returned when they could. They constructed a society not organized around estates or overseers, but around families, land parcels, and a kind of distributed independence that did not require formal recognition to function.

They were not prosperous. But they were not passive.

What outsiders often saw—what writers like Naipaul would later reduce to a kind of imperial debris, the “jetsam of an empire”—missed the essential fact. Jetsam is what is thrown away. It is what remains after something has been broken, stripped of purpose, cast off and forgotten.

Anguilla wasn’t that.

It was not discarded. It was left alone. And those are not the same thing.

The modern world arrived unevenly. There were moments, brief and partial, when Anguilla touched it. A telephone system, limited but real, connected parts of the island and extended outward. Communication existed—not easily, not universally, but enough to suggest connection.

Then Hurricane Donna came.

It arrived in September 1960 with the kind of force that does not need description so much as acknowledgment. By the time the wind begins to sound like something alive, there is nothing left to prepare. The island, already exposed by its geography, had nowhere to hide.

In one house near Island Harbour—a wooden structure, low and built to endure what it could—a family gathered as the storm approached. The father secured what he could. Doors reinforced. Windows covered. Anything loose brought inside or tied down. It was never enough, but it was what could be done.

By nightfall, the wind had risen beyond conversation. The roof did not fail all at once. It lifted, settled, lifted again. Each movement a warning. The children stayed close to their mother, not because they were told to, but because there was nowhere else to go. Rain forced its way through gaps that had not existed hours earlier. The house did not leak. It admitted.

At some point, the roof gave way.

Not entirely. Not cleanly. But enough.

The sound changed when it happened. Not louder—different. The boundary between outside and inside collapsed, and with it the illusion of shelter. The father moved to hold what remained, bracing beams that were no longer fixed to anything stable.

It was an act without guarantee.

They stayed through the night. There is no clear memory of when the worst passed, only that at some point the wind became something that could be heard again rather than endured.

Morning did not bring relief. It brought visibility.

What had been standing was no longer standing. Boats gone or broken. Trees uprooted, their roots exposed. The shoreline shifted in small ways that mattered—the familiar made unfamiliar.

And the telephone lines—thin, vulnerable, easily overlooked—were down.

Not damaged.

Gone.

The system that had connected Anguilla, however imperfectly, to itself and to the outside world had been erased in a single night.

Storms pass. Damage can be repaired. That is the expectation.

What defined Donna was not the destruction.

It was what followed.

Or more precisely, what did not.

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

Communication returned to word of mouth. Movement remained physical—boats, small aircraft, messages carried rather than transmitted.

It was not the storm that settled into memory.

It was the absence of rebuilding.

Because by then, Anguillians could see—clearly—that rebuilding was possible.

They had only to look south.

Seven miles.

That was the distance to St. Martin.

Seven miles is not distance. It is contrast.