The Undiscovered Country: Conservatism, Belonging, and the Emotional Life of Waldoboro

A talk by Michael Amico, given in conjunction with the ground-floor exhibition 19 Towns / 20 Stories and the ongoing mission of Open House of History, August 8, 2026


Waldoboro is often described as a conservative town. I've spent some time thinking about what that means, and I believe that its core is not primarily political but emotional: a resistance to being told what to do, what to think, or what to feel, and a determination to preserve one's own sense of worth and values.

In that sense, I recognize something deeply conservative in myself.

But when combined with economic insecurity, changing social conditions, political ideologies, disappointment, or personal loss, this feeling of conservatism can take very different forms.

It becomes wary, guarded, suspicious, withdrawn. People grow isolated, more resigned. They begin to feel forgotten or that there is no longer a place for them in the world. Hopelessness takes root. Sometimes substance abuse follows.

The 19 Towns / 20 Stories exhibition on the ground floor of Open House of History reminds us that substance use disorder is always experienced through the particular circumstances, relationships, and emotional conditions of a place.

I want to add another portrait to those represented there—the first person to work in the building as Collector of Customs. His name was John H. Kennedy.

By the early months of 1863, in the midst of the Civil War, Kennedy was overwhelmed. He had suffered financial setbacks, though he was not destitute. He lost his position as Collector of Customs after the election of Abraham Lincoln, since he was a member of an opposing political party. He became socially isolated. He was bullied and humiliated. He struggled to sleep. To quiet his thoughts, he took drugs to help him rest. He took too much. He never woke up. He died on March 30, 1863, at the age of forty-five.

I want you to know that Kennedy believed that slavery should remain a matter for individual states to decide.

What do you feel about him now? Was he the “wrong” kind of conservative? Was he a “bad” guy?

Many of us, craving order or simply trying to be understood ourselves, turn to these kinds of categorical distinctions and diagnoses, increasingly rigid ideas about ourselves and others. There is definitely a need and place for them, such as to help us get ahold of traumatic situations or explain what no one can fully understand or control. But when they become the default of how we think about and assess the world, when we stake our values and worth on them, we limit our view of the world and our emotional lives begin to compress into an ever present tense.

This very much describes the current state of the world. We are easily frazzled. Whatever our politics, we find ourselves perpetually on the edge of anger or disappointment, certainty or despair. That’s because the categorical distinctions and diagnoses, the rigid ideas, are always a stand in for the shared feelings between us all that we don’t give space to understand.

That is what haunts me about John H. Kennedy. Whatever his political views, he appears to have reached a point where his disconnected state felt permanent. Anger and resentment, anxiety and shame, hopelessness become harder to escape. There’s a feeling of nowhere else to go. Isolation grows. Every place feels the same. Even if flush with cash, disappointment lurks around the edges, ready to pounce.

I have been trying to understand the feel of Waldoboro, its conservatism, and the various qualities it can take, such as guardedness or resignation; trying to understand why this town developed differently from neighboring communities; and how its particular emotional relationships around authority, work, survival, and freedom continue to shape life here today. We’ve looked at how the circumstances of Waldoboro’s development affected people here, and how individuals, such as the earliest ministers, adapted to them in different ways, some more open than others. Now I want to look at how the class of men who ruled the town at its economic heights in the nineteenth century adapted to life here, and the effect that had on the town and also themselves.

These men, such as Colonel Isaac Reed, believed that the “good, rich, and wise” were most qualified to lead and that’s how they saw themselves.“Wise” meant degrees and credentials from elite schools. Rich meant what you think it means. Men like him believed a man without money was nothing. “Good” meant being active in church and government, but always with a hierarchical mindset. Isaac Reed believed in order and authority, a strong central government run by people like him. He was a Federalist.

John H. Kennedy was born in nearby Jefferson with only a common school education. He came to Waldoboro to study law with Colonel Reed. Kennedy wanted to get ahead, to belong, and that meant apprenticing to Reed and paying the social debts of entry into his class. Kennedy always called him “Colonel Reed”—which was an honorific given to prominent citizens who led local militias. Kennedy, by contrast, was familiarly called, in childlike manner, “John H.”

But for Reed, America was already rethinking the order and authority of government. The Federalists were a losing party. They were increasingly men without a country. People like Reed dug in and narrowed their personal feelscape into a forever present tense. They even considered seceding from the Union. And this was in the northern states, before the Civil War! At the Hartford Convention in 1814, during the War of 1812, New England Federalists proposed breaking away fro the rest of the country because they felt the wrong people were in charge of the country and national policies no longer favored them, or their wealth.

Now the Reeds were not all of Waldoboro. The shipbuilder Joseph Clark was the wealthiest man in this area of the state at his death in 1875. He built forty ships, as well as the town’s first theater, and was nationally known, as far away as New Orleans, as a “Black Republican”—an anti-slavery white man. Local historian Jasper Stahl says, compared to the Reeds, Clark’s fortune was not made in any part “through the exploitation of the necessities of the poor.”

By 1856, anti-slavery Republicans like Clark were even gaining votes in Waldoboro. And then one man stood up and, referring to the voters of the town, said “No!,” “I own them!” That man was Young Isaac Reed, the son. Born in Waldoboro, he ingratiated himself across town life by offering patronage and jobs to people less well off than he. In time, he would punish businesses and individuals who didn’t support him or his politics—stripping jobs from those who refused to vote as he ordered. People like him in town charged high interest rates and held meetings at inopportune times so that the poorer people could not attend and cast a vote.

Politics were tense in Waldoboro. In 1857, when someone raised a Border Ruffian flag—a pro-slavery banner—William Corcoran of Waldoboro, once a follower of the Reed machine, became an anti-slavery Republican. The Reed machine retaliated by digging an impassable ditch to cut off his just-reworked property from Main Street. By contrast, Reed’s house was noted as having a stone fence to protect it—portions of which still weave around us and the Waldo Theatre today.

Young Isaac was trying to claim power his father never fully attained nationally and projecting the family’s imagined national influence onto Waldoboro. He even secured the site for the new Custom House, now Open House of History, on his own land. His house was located where the Waldo Theatre stands today.

Meanwhile, John H. Kennedy was rising too: leading lawyer, county attorney, eventually state representative. Another lawyer of his day said, “Kennedy’s plain, simple manner of addressing a jury makes him a hard man to meet.” He was also deemed honest, generous, congenial. He built and lived in the brick house that still stands right across the entrance to Storer Lumber.

As the Civil War approached, Young Isaac delivered Waldoboro’s votes to James Buchanan, the politically proslavery candidate for the presidency, and as a reward President Buchanan appointed John H. to be the first Collector of Customs in the new building. It was a very remunerative post. His office was on the second floor. He was the first person to work in it. Thus the building became a fortress of the local Reed machine.

Jasper Stahl remarks in his history of Waldoboro that the Reed family were “men without a country,” and that under their sway, Waldoboro too could feel that way, a town without a country. The Reeds and their followers kept trying to have a different conversation than the broader state of Maine, one more aligned with the politics of the shipping economy of the slaveholding South. Their personal feelscape stretched far but thin.

Reed and his allies hosted Jefferson Davis, soon to be president of the Confederacy, here in Waldoboro. And who drove Davis through town in his fine chaise? Loyal Reed lieutenant John H. He must have been so proud. The evening culminated just next door, in a genteel dinner at Reed’s house.

But not everyone felt the same here. When Lincoln was elected, some residents lit candles in their windows. Joseph Clark strung an American flag across Main Street between his theater and the building opposite. When some men told him to take it down, he stood outside with a rifle: touch it and you’ll catch a bullet. The more recent intermittent flag wars on that same corner should ring a bell.

So which side was louder here—the anti-slavery voices or the states-rights voices? Which feelings had more power? They both held a lot of power because they both were resisting being told what to do, think, and feel—that deeply rooted core of local conservatism. Some of them wanted to rewrite the rules, to pull out of the Union and run off with the value they had built on the backs of many others.

But despite his wealth, Elder Reed was haunted by what he had not achieved—haunted by not holding the value he thought he deserved. He dreamed of becoming a national figure but was forgotten. Believing he was owed recognition but failing to secure it, he became a hardened man. His demeanor grew bitter and stubborn—not only from pride but from disappointment. Anger and resentment could hold the emotional space of the town hostage.

The same was true for his son. In 1845, Young Isaac confessed in a letter to his brother Charles that, even after achieving so much locally in public service, business, marriage, and property, he felt unsatisfied and lonely in Waldoboro, just as he was taking over from his father as head of the family machine. He certainly knew that not everyone in town agreed with or even liked him, and that the following he created in town was a forced one. He complained that another brother, William, had broken away politically, becoming what Stahl called the “black sheep” of the family—anti-elite, reformist, proto-populist, siding with what Isaac derisively called the “anti-Custom House party.”

How must Isaac have felt, stuck in Waldoboro, clinging to the maxim “a man without money is nothing”? Was he trying even harder to disprove it? Was his country only money? Disappointment, loneliness, and vulnerability are hard things to admit. Few want to speak openly about not knowing what comes next, or about being driven by uncertainty.

Others in town were speaking through other means. A group of local men about to ship out as Company A of the 21st Maine Regiment in 1862 during the Civil War, publicly burned John H.’s horse carriage—that proud symbol of elite connection, the very carriage in which he had paraded Jefferson Davis through town. Whereas the pro-South Copperheads like him had once dug ditches to destroy a Republican’s driveway access, the men about to leave for war destroyed a Copperhead’s smooth conveyance through town.

Instead of trying to decipher which side was right or wrong, let’s instead recognize how their act was not some kind of clear patriotic defiance. Many  local men had been pressured to enlist or lured by bounties. Their act against Kennedy was foremost one of anger; the anger of their own conservatism—anger at their leaders having gotten them into this mess of war, anger at having to go to fight that war, anger at the still dismissive and detached attitudes of elites like Reed and Kennedy, anger at being told by such men how to act, how to think, how to feel.

What was the issue of slavery “about” to people here who had never seen it firsthand? It was about value and how it was held by any one individual: whose labor counted; who felt taken advantage of; who felt degraded. Where was value to be found?

For John H., the reckoning was personal. His financial fortune was diminishing, and he, too, became a man without a country. John H.’s potlical fortunes took a turn as well. Since the Collector of Customs was a political appointee, the post here went to Republican Sebastian Marble, future Governor of Maine, after Lincoln was elected. This building became the most prominent and visible space in town where national-level allegiance shifted.

I imagine John H. walking down the street, with his “genial disposition” and “simplicity and carelessness of dress,” as early town historian Samuel Miller describes. Jasper Stahl describes Kennedy’s “whimsical humor” and “affected indifference in dress” that made him a kind of “village institution.” Rising from a common background in Jefferson, did he feel out of place even among his good, wise, and rich peers? If he had, like the Reeds, renounced the Union, did he feel guilty now for having gone along? Gullible or trapped?

Perhaps John H. was also a man without a family. He had stood by Isaac Reed when Reed’s own family fractured politically. Yet it was John H.’s carriage that townsmen destroyed, not Reed’s property. Did he feel abandoned? Did he even feel he belonged among the Reeds?

One of the most widely read stories of the Civil War era was Edward Everett Hale’s “The Man Without a Country.” That’s actually where Stahl got the phrase “men without a country” that he applied to the Reeds—and it applies to Kennedy, too. The story was aimed directly at Southern sympathizers, draft resisters, and those who tried to tune out the war.

The tale follows Philip Nolan, a bright, eager, ambitious soldier drawn to Aaron Burr—proud and imperious, dreaming of founding his own nation, much like Elder Reed. When Burr falls, Nolan follows and is convicted of treason. In court he cries out that he never wants to hear the name of the United States again. His punishment is lifelong exile at sea, with the name of his country never to be spoken in his presence again.

For fifty years, Nolan drifts among ships, far out on the ocean, forgotten. Once eager to be a hero, he becomes nobody, with only a rotating cast of sailors for company. But it’s in that condition that he comes to feel more and more the need for home. Detached and floating out at sea, he slowly realizes that for his sacrifices to mean anything, he needs to belong to something larger—a community if not a nation, a home that could honor him. Without that, he was nothing. In the story, Nolan dies in 1863—the year Kennedy will die as well—Nolan clutching his father’s Revolutionary War mutual-aid society medal. In his ship’s cabin, Nolan had hidden an American flag.

Here in Waldoboro, a ship called the Union Flag was built and launched out to sea in 1862. And can you believe it: One of the other ships built and launched to sea from here that same year bore Kennedy’s own name: the John H. Kennedy. Off to sea. Or, as men who slipped draft duty by boarding ships went off to, as one newspaper put it, “the undiscovered country”—a phrase from Hamlet meaning death, or the unknown after death. Reportedly, John H. Kennedy, the ship, was headed to the southern slavery stronghold of New Orleans.

Kennedy, the man, was drifting. Where was he to go? Stahl writes, “His last years were clouded.” The world was collapsing, overwhelming. His feelings were all present tense.

“John H. could not sleep,” Stahl tells us. So he bought a sleeping medicine, and seeking to bottle up the feelings that were swamping him, he drank it, entered the “undiscovered country,” and was gone, [blow out candle] never to wake up. The doctor who gave him the dose soon left town.

For Kennedy, the space to think and feel more freely—the space of history—had collapsed. Anger, resentment, fear, hopelessness had clouded out the complex world of reality.

It was Jasper Stahl who first included the details about John H.’s death in the town’s history, Stahl who was drawn to the feeling of the scene. For Stahl, doing history meant letting “his imagination linger between the lines,” as he tells us in regards to diary of a local man who fought in the war.

I have been trying to open up the feelings of Kennedy and the men around him into the relationships and conditions that shaped them, and the town, and so us, opening up the space of history to find where our feelings take root and sitting within those emotional circumstances.

Can we stay here, not assigning but wondering at the feelings this building has held over time, at the different positions and beliefs represented here and the relation between them, asking what lies behind the labels we give to people and places, exploring the specific conditions that gave rise to the feelings that animate them, allowing the meanings of the past to continue to unfold and affect us, opening up the present tense of our understandings to meet one another—anyone who has passed through here or is pictured or felt here—in the feelscape of time.

We gather in a building that has continually expanded what it means to share values as a community: first as a Custom House collecting taxes, then a Post Office carrying letters, then a library exchanging books, and now an Open House of History exploring the emotional forces that shape our lives and tending to the vulnerability of the people we encounter.

We continue to move from what has been dictated and settled toward what is still waiting to be heard, felt, imagined, seen, toward the relationships and possibilities that our fixed identities and ideas have overlooked or silenced.

In this space, I feel most myself—absolutely distinct—and most like others—absolutely akin. I feel the limits of life and the fallibility of each one of us. I feel empathy. It is not all sad. It is a looseness of expression that can be joyful. It is what we feel among a diverse group of people talking, laughing, debating. It is, above all, a feeling of freedom, at times painful as well as pleasant, and always opening the space of feeling more, of something larger, connecting us with other people and what comes before us, an undiscovered country.

The man John H. Kennedy had passed away but the the ship John H. Kennedy continued to sail the seas, for adventure, culture, new riches, new values, far into the unknown, looking for home.