How much must happen—in the world and community, to our neighbors, within our families—before we act? When things get dangerous, do we stay or leave?

In 1936 my grandparents applied for and received permission to emigrate from Germany to the United States. Instead of going immediately, they remained in their home until September 1938, months following the first state-ordered detainments of so-called “criminals.” What kept them there for two more dangerous years? There is no one alive to answer this question, only an incomplete paper trail. A few weeks after my grandparents finally left, the National Socialists declared all German Jewish passports invalid. This history haunts me when I hear the news today, with its stories of fear, hiding, and deportation. So many of us face similar decisions right now.

Our experiences and the times in which we live shape the way we look at history. Today, as I work on the American painter John Singleton Copley, who will feature prominently in our refreshed galleries of 18th-century Art of the Americas, I envision not only the politics, but the human stories: the artist and many of his Boston subjects riven by indecision, living, on the eve of the Revolution, in a town fractured and factionalized by politics and occupied by armed troops. The Declaration of Independence had yet to be written, but the idea of accountability, even separation, from Great Britain in response to its sanctioned infringement of colonists’ rights was already being debated. Fear of consequences rattled both sides, tempers were high, violence incipient. When things got dangerous, did people stay or leave? When did they decide to make a move or take a stand?

Copley’s portrait of Isaac Winslow and his second wife, Jemima Debuke Winslow, unwraps one of these human stories for me. By the early 1770s, when he made this painting, Copley was the best artist in Boston, and his work was costly. In consequence, most of his mature portraits represent the city’s wealthy upper classes, all of them white and many of them merchants engaged with an international economy that relied heavily on enslavement. A good number were Loyalists, faithful to the King and fearful of how the war would impact their trade. Isaac Winslow was a case in point: a Harvard man, a wealthy businessman with ships, owner of a vast tract of land along the Kennebec River in Maine, proprietor of a country estate in Roxbury, and an enslaver. His family believed in marking its passage through time with portraits, a practice they had begun in the 1650s. Isaac ordered two pendant portraits from Robert Feke in about 1748, one depicting his first wife, Lucy Waldo Winslow, and the other of himself overlooking a landscape. A few years later he bought a large canvas from Joseph Blackburn representing him with Lucy and their two daughters. Two years after Lucy’s death, Isaac remarried; his new bride, Jemima Debuke, was the daughter of another Boston shipowner. It was time for another portrait, this one commissioned from Copley.

Like all portraitists, Copley worked with his sitters to achieve both his own artistic goals and their social aspirations. And, like many businessmen, Winslow among them, Copley tried to maintain his market by staying publicly neutral in troubled times. He painted many progressive liberals who have become our national heroes—John Hancock, Samuel Adams, Joseph Warren, Paul Revere, Mercy Otis Warren—but he also had numerous Loyalists, even British officers, as clients. He rendered them all equally beautifully in paint. For Isaac and Jemima Winslow, Copley devised a double portrait, a compositional device he was just beginning to explore. In the painting, the couple sit together at a mahogany table, Isaac every inch the country squire in riding clothes, Jemima the consummate hostess in expensive British silk.

But the peaceful interlude Copley invented did not last long. Within months, both the painter and his sitters were drawn into the heart of conflict, when an enormous shipment of tea was dumped in protest into Boston harbor. That tea was consigned to seven Bostonians, among them the family of the wealthy importer Richard Clarke. Clarke was Isaac Winslow’s brother-in-law and Copley’s father-in-law.

The incident forced each man to take a stand. Both chose family. Copley tried to mediate, but soon realized hostilities were inevitable. He left Boston in June 1774, making a long-planned trip to Italy to see the great works of art he had dreamed about. He reunited with his family in London in 1775 and never returned to America. And the Winslows? Feeling threatened, they left their Roxbury home for Boston soon after the battle at Lexington in April 1775. In 1776, after George Washington’s colonial militia drove the British from Boston, the Winslows joined a Loyalist evacuation to Halifax. They took their painting with them.

It was not a happy ending. Isaac, then in his late sixties and doubtless weakened by supply shortages and uncomfortable and anxious travel, made out his will in Halifax, mentioning “the doubtful state of my affairs.” He and Jemima left for New York, then in British hands. Isaac died there in March 1777. Jemima and her son Thomas then joined her sister Elizabeth, wife of another Boston Loyalist merchant, on the long voyage to England.

The Winslows had waited too long to make their move. But Jemima still had Copley’s canvas, a memory of the world and the husband she had lost.

I still have many things my grandparents managed to take from Germany. When I see them, inevitably I think of what my grandmother called “former times.” Objects hold many different stories, sometimes of love and loss, or of decisions about what to take and what to leave behind. They can represent resilience or show evidence of compassion. It is up to us to choose what we want to see.