Frederick Douglass: From Slave to Leader - ESCAPE!


Escaped slaves, circa 1862, under the protection of Union General Lafayette.  Photo, by Mathew Brady, now public domain and maintained at Yale University.  Online, courtesy Wikimedia Commons.


As he grew older, and was hired out as an employee who worked for others, Frederick Douglass was forced to give all the money he earned to his master. Not only was he outraged about this unacceptable predicament, his plight caused the now-literate slave to think about escaping from his unchanging environment.

I was now getting...one dollar and fifty cents per day. ($26.37 per day in 2003 dollars.) I contracted for it; I earned it; it was paid to me; it was rightfully my own; yet, upon each returning Saturday night, I was compelled to deliver every cent of that money to Master Hugh. And why? Not because he earned it, - not because he had any hand in earning it, - not because I owed it to him, - nor because he possessed the slightest shadow of a right to it; but solely because he had the power to compel me to give it up. (Narrative, page 99.)

The first time Frederick Douglass tried to escape, he was caught and spent months in jail. By 1838, he was working as a caulker in a Baltimore shipyard and had many good friends in the city. One of those friends was a black free-woman named Anna Murray.

Increasingly weary of turning over income to his master, and of his bondage in general, Frederick picked Monday, September 3, 1838, as his escape day. By this time, he and Anna Murray had fallen in love; she gave him some of her savings to help him as he made his way north to a non-slave state.

To protect those who assisted him, Frederick did not provide details of his escape in his first two autobiographies. Only from his third book, Life and Times of Frederick Douglass, written much later in life, do we know those details.

Frederick had obtained a Seaman’s Protection Certificate from a free black free sailor (such as this 1854 document held by the Library of Congress) to help him get past railroad conductors, and others, who would check his identity papers. The documents he held did NOT match his physical description. If anyone scrutinized the Certificate, Frederick would be "found out."

Dressed as a sailor, Frederick left Baltimore bound for New York City:

In my clothing I was rigged out in sailor style. I had on a red shirt and a tarpaulin hat and black cravat, tied in sailor fashion, carelessly and loosely about my neck. My knowledge of ships and sailor's talk came much to my assistance, for I knew a ship from stern to stern, and from keelson to cross-trees, and could talk sailor like an "old salt." On sped the train, and I was well on the way, to Havre de Grace [in Maryland, his home state] before the conductor came into the negro car to collect tickets and examine the papers of his black passengers. This was a critical moment in the drama. My whole future depended upon the decision of this conductor. (Life and Times of Frederick Douglass, page 198.)

For some reason, the conductor (who had been harsh with other passengers) was surprisingly calm with Frederick:

"I suppose you have your free papers?" To which I answered: "No, sir; I never carry my free papers to sea with me." "But you have something to show that you are a free man, have you not?" "Yes, sir," I answered; "I have a paper with the American eagle on it, and that will carry me round the world." With this I drew from my deep sailor's pocket my seaman's protection, as before described. The merest glance at the paper satisfied him, and he took my fare and went on about his business. This moment of time was one of the most anxious I ever experienced. Had the conductor looked closely at the paper, be could not have failed to discover that it called for a very different looking person from myself, and in that case it would have been his duty to arrest me on the instant, and send me back to Baltimore from the first station. (Life and Times, page 199.)

Onboard the train, Frederick saw people who would have recognized him had he not been wearing sailor clothes. But when he left the train at Wilmington, Delaware (the "last point of imminent danger"), to catch a ship for Philadelphia, no one suspected he was a runaway.

Within twenty-four hours of his Baltimore departure, "Fred" reached the free soil of New York City. (Later, his escapade was memorialized - and fictionalized - in song and verse.)

On September 15, 1838, days after his escape, he and Anna were married in New York. Frederick changed his last name from Bailey to Douglass, after the lead character in Sir Walter Scott’s poem The Lady of the Lake.

As the wife of a man about to become world-famous, Anna’s public persona would soon be obscured by the stature of her husband. Who was this woman who remained such a support and inspiration to Frederick for nearly five decades?

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Author: Carole D. Bos, J.D. 5155stories and lessons created

Original Release: Feb 01, 2005

Updated Last Revision: Jan 31, 2017

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