When Freedom Changes Flags: A Family Story of Portugal, America, and the March of Time

My father left Portugal in 1966, a young man escaping a country that no longer felt like his own.

He had been born into a strange political paradox—a hybrid authoritarian state where elections were still held, but only one political party mattered. Portugal’s prime minister, António de Oliveira Salazar, had been called to power in the late 1920s by the same military government that ended the First Republic. Over the years, he consolidated near-total control. By the time my father came of age, real elections had been shelved, and anyone who spoke out faced the wrath of the state police, PIDE, and its web of political prisons.

António Simões

Liberty didn’t just disappear overnight. It slipped away, quietly- slowly, until it was gone.

After he was called to fight in the Colonial War—Portugal’s misguided attempt to hold onto its African colonies—he returned home with a different understanding of empire, justice, and identity. He had seen colonialism up close. It wasn’t just theory, and it was not what they had told him

Disillusioned and carrying nothing but a military passport, he married an American woman he had met before the war and moved with her to her hometown: Chicago.

There, he became a proud American. He never missed a chance to vote. He believed in free speech. He raised a family. And he never fully returned to Portugal—even after the dictatorship fell in the peaceful 1974 Carnation Revolution. For him, America was freedom. Portugal was a memory.

And yet, here I am—his son—watching the world shift beneath my feet. As had he.

Portugal, the country he once fled for lack of liberty, is now considered more democratic and freer than the United States by several global indexes. The Freedom in the World report and Democracy Index consistently place Portugal well ahead of the U.S. in terms of civic freedoms, press independence, and the strength of democratic institutions.

In healthcare and education, Portugal outperforms despite spending much less. Its national healthcare system is ranked among the world’s best for quality, access, and affordability. U.S. healthcare, for all its billions spent, still leaves tens of millions uninsured or underinsured—and consistently ranks much lower in health outcomes.

Portugal’s public safety also tells a story. The crime rate in the United States is 81% higher than in Portugal, according to NationMaster. Gun violence, in particular, remains almost nonexistent in Portugal compared to the daily shooting across the U.S.

And in a world growing more anxious, Portugal has quietly held its ground. The World Happiness Report shows the U.S. slipping in the rankings while Portugal continues to edge upward, fueled by community, simplicity, and stability.

The irony hurts: The place my father escaped from in search of freedom may now offer more of it than the country he fled to.

It’s not about regret. My father found dignity and freedom in America. He believed in its promise. But he also knew something we often forget: freedom isn’t guaranteed. It’s not owned by one nation, no nation is exceptional. Freedom is cultivated, defended, and cherished. And it can fade if we stop paying attention.

The late Supreme Court Justice David Souter had a moment of future clarity in 2012 when he said:

“I don’t believe there is any problem of American politics in American public life which is more significant today than the pervasive civic ignorance of the Constitution of the United States and the structure of government. An ignorant people can never remain a free people. Democracy cannot survive too much ignorance.”

History doesn’t shift in straight lines. It turns back on itself. It loops and it humbles. Sometimes, it forces us to look at where we came from, and wonder who we’ve become. And sometimes we just forget who we are, and where we came from.

And maybe, just maybe, it asks us to imagine that the next chapter might be written in a place we thought we’d left behind.

As I reflect on two nations, two paths, I am pulled to the words of Fernando Pessoa, Portugal’s 20th century poet, who wrote: “To be great, be whole: nothing that’s you should exaggerate or exclude. Be complete in each thing.”

Pessoa reminded us that our sense of identity—national or personal—is not fixed at one point. We are shaped by many places, many selves, and many histories. My father was shaped by Portugal and became American. I, in turn, feel shaped by both—and pulled by the future as much as by the past.

Eras sobre eras se somem

No tempo que em eras vem.

Ser descontente é ser homem.

Que as forças cegas se domem

Pela visão que a alma tem!

E assim, passados os quatro

Tempos do ser que sonhou,

A terra será teatro

Do dia claro, que no atro

Da erma noite começou.

Pessoa saw time as layered, restless, and more than simply human. That dissatisfaction is part of our condition—and so is the vision to dream beyond it. My father’s journey was a step away from darkness. And now, as the world turns I can say that Portugal becomes a beacon in its own right - a new day rising from an old night.

Pessoa and Souter. My father and I. To be whole is to hold both shadow and light. And to be free is to keep walking, watching, and wondering—as eras do fade, and new ones begin.