In February 2024, historian Dr.James Crawford was cataloging antebellum photographic collections at the Library of Congress when a particular daguerreotype from September 1856 stopped him cold.

The image depicted the wealthy Caldwell family of Richmond, Virginia, posed in an opulent interior, accompanied by a young Black boy named Benjamin.

At first glance, the portrait appeared typical of the era—a display of wealth and status, with an enslaved child standing rigidly alongside his enslavers.

But upon closer examination, James noticed something extraordinary: Benjamin was clutching a small metal key in his hand, a key that would unlock a story of resistance, sacrifice, and hope.

 

Daguerreotypes, early photographic images known for their sharp detail, often captured the formal, posed lives of antebellum Southern families.

Enslaved children like Benjamin were often included as part of the household “property,” positioned stiffly beside their owners.

But Benjamin’s key was a secret act of defiance hidden in plain sight.

The key was likely one used for shackles, manacles, or chains—tools of oppression wielded to control enslaved people.

 

The discovery raised urgent questions: How had Benjamin come into possession of this key? What was he planning? And what consequences would he face if caught?

James delved into the Caldwell family’s extensive records at the Virginia Historical Society.

The Caldwells were prominent tobacco merchants, wealthy and influential in Richmond.

Among the ledgers, Benjamin was listed as a seven-year-old house servant, son of Rachel, the family cook, and Samuel, a field worker who had died in 1854.

The ledger’s terse note “deceased” masked a brutal truth: Samuel’s death was likely a punishment for his resistance, a fact hinted at in family correspondence.

 

Ellaner Caldwell’s letters revealed tensions within the household.

In August 1856, she wrote about troubles with Benjamin, describing him as “sullen and disobedient,” influenced by grief over his father’s death.

Thomas Caldwell threatened to sell the boy if his behavior did not improve—a common threat used to discipline enslaved children by threatening separation from family.

A diary entry from Thomas Caldwell dated October 12, 1856, confirmed James’s fears: the key Benjamin held had been stolen from the family’s basement storage, where shackles and chains were kept.

Evidence of tampering was found, and Benjamin was questioned. The boy was to be sold “south immediately” as punishment—a fate that often meant brutal labor and near-certain death for children.

 

Benjamin’s story took a harrowing turn as James traced his sale to a sugar plantation in St.Charles Parish, Louisiana.

Plantation records documented injuries Benjamin suffered during his four months of forced labor—burns and lacerations typical of the grueling “Grinding” harvest season.

But then, something unexpected happened: Benjamin was sold to Josephine Lauron, a free woman of color in New Orleans, who paid a significant sum to rescue him.

 

Josephine Lauron was no ordinary buyer. Born free in New Orleans, she had inherited property and wealth, which she used to purchase enslaved individuals—often children—to protect or free them.

Letters between Josephine and Rachel, Benjamin’s mother, revealed a clandestine network working to save enslaved people.

Rachel had managed to send word from Virginia to New Orleans, pleading for her son’s rescue.

 

Further research uncovered Rachel’s involvement in the Underground Railroad and resistance efforts.

The First African Baptist Church in Richmond, where Rachel was a member, served as a hub for freedom seekers.

A Quaker abolitionist’s diary described a “sister” in Richmond providing shelter and aid to escapees, likely Rachel.

Thomas Caldwell’s letter to authorities accusing Rachel of suspicious activity confirmed the danger she faced.

 

Benjamin’s theft of the key was more than a desperate act; it was a continuation of his family’s resistance.

He had used it to unlock shackles and help two people escape before being caught.

The punishment—being sold away from his mother—was devastating, but Benjamin’s story did not end there.

 

Under Josephine Lauron’s care, Benjamin was educated and nurtured. Letters showed he learned to read and write rapidly and spoke often of his parents’ courage.

When Union forces captured New Orleans in 1862, slavery effectively ended there, and Benjamin was formally manumitted.

He then worked with Union forces, helping establish schools for formerly enslaved people.

 

After the Civil War, Rachel gained her freedom and reunited with Benjamin in New Orleans after nine years apart.

Together, they dedicated themselves to education and civil rights.

Benjamin became a teacher and leader, advocating for voting rights and equality during Reconstruction.

Rachel taught literacy and domestic skills to freedwomen.

 

Benjamin’s 1867 speech before the Louisiana Equal Rights League famously invoked the key he held as a child as a symbol of knowledge and freedom.

He reminded listeners that every lesson learned was another key unlocking chains of oppression.

Benjamin married, raised children, and continued his work as an educator and politician until his death in 1914.

His obituary noted that he kept the iron key from his childhood as a reminder of his origins and the power of education.

His descendants carried on this legacy, including Denise Freeman Carter, a principal in New Orleans who treasures the original key passed down through generations.

 

Inspired by Benjamin’s story, the Smithsonian’s National Museum of African American History and Culture created a special exhibition titled *The Key to Freedom*.

It featured the 1856 daguerreotype, the key itself, letters, speeches, and photographs spanning five generations of the Freeman family educators.

The exhibition became one of the museum’s most visited, sparking nationwide interest in uncovering hidden stories of resistance in antebellum photographs.

 

Benjamin’s story teaches us that even in the darkest times, acts of courage and resistance persist.

His key, both literal and symbolic, represents the power of knowledge, education, and the human spirit to overcome oppression.

Schools across the country use his story to inspire children to see themselves as holders of keys—keys to justice, equality, and freedom.

 

What began as a simple family portrait from 1856 has unfolded into a profound narrative of resilience and hope.

Benjamin Freeman, a seven-year-old enslaved boy secretly holding a key in his hand, risked everything to help others gain freedom.

His survival, education, and lifelong dedication to teaching affirm that resistance is possible at any age and that knowledge remains the most powerful key of all.

 

This story, preserved through photographs, letters, and family memory, challenges us to look deeper at history and recognize the courage hidden in plain sight.

Benjamin’s legacy lives on—not just in museums and books, but in classrooms and communities where the fight for freedom and equality continues.

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