As Frederick Douglass approached the bed of Thomas Auld, tears came to his eyes. He had not seen Auld for years, and now that they were reunited, both men could not stop crying. Douglass and Auld clasped hands and spoke of past and future, confronting death and reminiscing over their years of acquaintance and separation.

Auld wasn’t an old friend of Douglass’s—he was his former owner. But now, the two men stood on different terms. For years, Douglass had spoken out against Auld’s cruel treatment of himself and his family members, becoming one of the nation’s most recognizable abolitionists and advocates for equal rights for African-Americans. Now, with the abolition of slavery, Douglass could confront his former master without fearing arrest or re-enslavement.

The 1877 meeting was one of a series of moving encounters Douglass had later in life with those who once held him in bondage. Fraught with strong emotions and bitter memories, the meetings show how determined Douglass—one of the most morally and politically influential African-American public figures of the 19th century—was to confront the legacy of slavery in his own life, in private as well as in public.

Douglass, born into slavery in 1818 on Maryland’s Eastern Shore, wasn’t always owned by the Auld family. After living with an aunt and his grandmother, he was sent to serve at the Wye Plantation in Talbot County, Maryland. There, he saw the brutality of slavery on full display. His owner and overseer, Aaron Anthony, fed enslaved children from troughs and mercilessly whipped slaves who did not obey his orders quickly enough.

When Frederick was about 10, he was given to Anthony’s daughter, Lucretia Auld. She and her husband Thomas sent Douglass to serve his brother, Hugh, in Baltimore, where he learned to read while working in his owner's house. In 1833, after Thomas and Hugh got in a dispute, Thomas took back the enslaved workers. Douglass returned to Thomas’s estate the same year and resumed work as a field hand.

Thomas was a cruel master, starving and beating his enslaved workers and breaking up their attempts to worship, read and write. He leased Douglass out to other masters who attempted to break his independent spirit with physical and emotional abuse. Eventually, Douglass returned to Hugh in Baltimore, fell in love and started a family. This increased his hatred of slavery and in 1838, at the age of 20, armed with fake papers, a sailor suit disguise and hope for the future, he escaped to the free North with the help of Anna Murray, the free Black woman from Baltimore with whom he had fallen in love. They ended up in Rochester, New York.

As a free man, Douglass couldn’t forget the people he’d left behind in Maryland—or the masters who had enslaved him. He became involved in the abolitionist cause, started publishing his own abolitionist newspaper, The North Star, and associated with notable abolitionists like William Lloyd Garrison in his fight against slavery. His firsthand descriptions of the cruelty of slavery were a potent weapon in the struggle against bondage, and Douglass became a renowned speaker, crisscrossing the North to speak to abolitionist groups and gatherings about his life as an enslaved person.

In 1845, Douglass increased his renown with the publication of Narrative of the Life of Frederick Douglass, an autobiography that painted a grim picture of his life in slavery. (Later, he updated it to include more information about his escape and later life.) In the book, Douglass named his former owners, who had been attempting to capture him using bounty hunters who specialized in tracking down people who escaped enslavement. To avoid capture, Douglass fled to Great Britain, but quickly returned to the United States to continue his crusade against slavery, after a group of supporters paid for his freedom.

In 1848, Douglass again turned a spotlight on his former owner. He wrote an emotional open letter, to Thomas Auld, lambasting him for his participation in a cruel system. “I intend to make use of you as a weapon with which to assail the system of slavery,” wrote Douglass. Yet he ended the letter on a surprisingly tender note. “I entertain no malice toward you personally,” Douglass wrote. “There is no roof under which you would be more safe than mine, and there is nothing in my house which you might need for your comfort, which I would not readily grant…I am your fellow-man, but not your slave.”

A few years later, Douglass met a member of the Auld family in person for the first time since his escape. Amanda Auld Sears, Thomas’s daughter, approached Douglass after an 1857 lecture in Philadelphia and invited him to visit her at home. Amanda’s views on slavery had changed in her adulthood, and she had become an anti-slavery advocate despite the tensions this created in her family. During their emotional meeting, Amanda and Douglass reminisced about their shared childhood. Douglass also used the time to ask about his family members, who were still owned by Auld.

Amanda and Douglass kept in touch, and in 1877, near the end of Thomas’s life, Thomas and Douglass finally met again. When they did, neither man could keep their emotions in check.

“Frederick,” said Auld, “I always knew you were too smart to be a slave, and had I been in your place, I should have done as you did.”

“I did not run away from you,” Douglass replied. “I ran away from slavery.” Douglass later published an account of the meeting in newspapers of the day and included it in a later memoir.

During the meeting, Douglass apologized for blaming Auld for mistreating his grandmother, and found out his real birth date. They discussed death and parted as friends. Though personally reconciled to his former master, Douglass—and the 4 million enslaved people who had been emancipated at the end of the Civil War—could never be reconciled to the institution itself. He translated this rage into meaningful work on behalf of African Americans, even after the institution of slavery was gone.

“Slavery is indeed gone, but its long, black shadow yet falls broad and large over the face of the whole country,” he said during an 1881 speech at Storer College in West Virginia.

At that point, Douglass’s campaign against slavery had ended. But his fight for equality and civil rights for African Americans outlasted both the institution and the owner who had made his young life so miserable. His encounters with that former owner and family members underscored his belief that forward progress was possible—even when it was emotionally fraught.