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Politics & Government

The Great Escape of Judah P. Benjamin

Following the fall of Richmond at the close of the Civil War, Confederate Secretary of State Judah P. Benjamin made his escape through Florida and what is now eastern Pasco County.

Perhaps the New York Times put it best on August 3, 1865, when they reported the “mythical escape” of Confederate Secretary of State Judah P. Benjamin through Florida.

But, what few realize and what wasn’t reported is that Benjamin’s great escape led him on a course through what is now Pasco County, after a week long stay in Brooksville.

From U.S soldiers and twentieth century writers, Benjamin’s “mythical escape” has been recounted by many, and today still lives on.

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Who was Judah Phillip Benjamin?

Judah P. Benjamin was born August 6, 1811, in St. Thomas, Virgin Islands to Phillip and Rebbecca de Mendes-Benjamin, who, by 1818, had settled in Charleston, South Carolina.

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After graduating from Fayetteville Academy in 1824, the young Judah went on to studies at Yale University, and from records at Yale appears to have been enrolled for at least three terms, with his name appearing in the catalogues for 1825, 1826, and 1827.

However, in early 1828, before earning a degree and with only $5 in his pocket, Judah moved to New Orleans.

There, he found short employment in a mercantile business before entering a more congenial position as a notary’s clerk.

After regular business hours Judah engaged in the study of law, and, on December 16, 1832, joined the Louisiana Bar where he quickly moved into prominence. Climbing through the ranks of politics as a lawyer, he was eventually elected to the Louisiana lower house of the general assembly on the Whig ticket.

Harper's Weekly once reported, "The Hon. J. P. Benjamin, of Louisiana, Attorney-General, is distinguished as one of the profoundest jurists and most accomplished advocates in the country. He is of the old line of Whig class of State Rights politicians."

In 1852, he was elected by the Louisiana legislature to serve their state as U.S. Senator; the second Jewish senator in U.S. history. The first was David Levy Yulee, who Benjamin was related to by marriage.

Benjamin's personal appearance was not at all impressive. In figure, he was short, fat, and pudgy with half a smile about his mouth that sometimes seemed to degenerate into a simper.

But, his kind manner made up for his lack in appearance and he was considered gentle, sympathetic, and absolutely unaffected.

According to the Escape of Judah P. Benjamin, he served in three different cabinet positions under the Confederacy, his first position, Attorney General, came early on in 1861.

By September 1861, he took to the office of Confederate Secretary of War, and by March 1862 moved into the office of Secretary of State — a position he held until the end of the war.

And, while Judah was well-liked, he was very reserved when it came to both his private and professional matters, perhaps a trait that Confederate President Jeff Davis liked.

Among his golden rule was to destroy any and all correspondence or anything that might aid or enlighten a person who shouldn't be enlightened.

In April 1883 Benjamin wrote,

"I have never kept a diary or retained any copy of a letter written by me. No letters addressed to me by others will be found among my papers when I die. With perhaps the exception of Mrs. Jefferson Davis, no one has many letters of mine; for I have read so many American biographies which reflected only the passions and prejudices of their writers, [for] that I do not want to leave behind my letters and documents to be used in such a work about myself"

Benjamin’s position was no more evident then when the Confederate capital fell in Richmond and when his last days there were spent burning the secret service papers of the Confederacy.

But, it was after Richmond’s demise where our story begins.

Judah Benjamin’s Great Escape

According to military reports, on May 1, 1865, word had reached Union troops that Jeff Davis and other prominent rebellion leaders might attempt their escape through Florida.

Union orders were handed down to picket the mouths of the Suwannee, Wacasasse, Withlacoochee, and Crystal Rivers, and the significant ports of Cedar Key and Bayport.

And, with the Florida border in mind, two days later, on May 3, 1865, Benjamin broke away from President Davis and their escape party near Washington, Georgia.

According to a letter to Mrs. Jefferson Davis, Benjamin came to the President and said,

“I could not bear the fatigue as you do, and as I can serve our people no more just now, will you consent to my making an effort to escape through Florida? If you should be in condition to require me again, I will answer your call at once.”

One week later, on May 10, 1865, President Davis and the remaining cabinet members were captured at Irwinsville, Georgia.

However, Benjamin had already made his get away. But, before leaving Georgia, with a Confederate passport in hand, he took on the disguise of a Frenchman traveling through the south, prospecting for property.

Having grown a full beard since escaping from Richmond, Benjamin donned a hat, goggles, and a cloak to become the French character he was playing — M.M. Bonfals, which interpreted means “good disguise.”

From there Benjamin traveled south into the sparsely populated areas of Florida where his adventuresome journey began.

Its believed that he entered our state through Madison County, where he quickly changed his alias to that of a famer who was traveling in search of land to settle with friends from South Carolina — one his most successful disguises.

With aid from a kind farmer and his wife, he adorned home-spun cloths and acquired what he referred to as "the commonest and roughest equipment" for his horse.

Travels were slow, however on Mary 14, 1865, two weeks after leaving the escape party in Georgia, Benjamin finally crossed the Suwannee River — now using the fictitious name of farmer Charles Howard.

Intending on heading east to the Indian River, his plans quickly changed when he learned of a lack of sailing vessels there and the great risks of being detected.

So, he headed to the western coast where travels brought him to Brooksville sometime on or about May 19, 1865.

Here, Benjamin sought out , captain of the local home-guard, and produced to him a letter from his “South Carolina friends” introducing him as farmer Charles Howard and asking for Lesley’s assistance in his travels south.

However, upon producing the letter Benjamin made himself known to Lesley, after which he was taken to the family’s plantation where plans were set into motion.

While staying in Brooksville Benjamin’s identity was kept a secret, with the exception of a few who had been loyal to the Confederate service.

According to Confederate Veteran Magazine, among those to learn of Benjamin’s identity was Captain Samuel Hope, who also had the pleasure of conversing with the high-ranking cabinet member — no doubt, an honor for the captain.

After a week long stay in Brooksville it was time for Benjamin to continue on his journey.

Plans called for his escape to Cuba, but Benjamin objected giving reason that he had little confidence of finding protection under such a weak Spanish Government. He wished to be taken to the Bahamas since the British Government had professed a friendship for the Confederacy during the war.

Taking care to elude Union captors, Capt. Lesley guided his companion, by buggy, through Hernando County.

According to historian Bill Dayton, it’s likely the party would have taken the Toadchudka Road, which follows part of the modern Handcart Road through eastern Pasco.

Their destination was the Gamble Plantation in Manatee County.

Upon arriving at Gamble, Benjamin was introduced to owner Archibald McNeil, who was reluctant to open his home to the weary travelers, but eventually gave in.

After nearly a week and one Union raid on the Gamble Plantation, Benjamin was transferred to Bradenton and the home of Captain Frederick Tresca, who would be the one to carry him to safety by sea.

On June 23, 1865, Secretary Benjamin, Captain Frederick Tresca and Hiram A. McLeod departed from Sarasota Bay aboard their small vessels bound for the Bimini Islands.

However, the journey proved to be a dangerous one with the vessel being detained by the Union on at least one occasion.

By this time Benjamin had already shed his farmers disguise and was now acting as a cook. With his apron and greased smeared face he was able to avoid detection.

But, finally, on July 10, 1865, they arrived safely to their destination and Confederate Secretary Judah P. Benjamin had made his great escape from the country.

Eventually he made his was to England where he had previously shipped, according to his own account, six or seven hundred bales of cotton from which Benjamin received only one hundred bales, which sustained him for a few years.

Benjamin later compensated his income by working for a local London newspaper while engaging in the studies of English Law and eventually served as Counsel to the Queen, this was the beginning his new life,

Eventually he was given amnesty by the United States for his support and work with the Confederacy. However, he never returned to the U.S.

In 1883, he retired to Paris where his wife and daughter had lived for years since the U.S. conflict that made Benjamin so famous. It is said that even in Paris Benjamin tried to escape notice.

However, on May 6, 1884, less than a year after retiring and 19 years after making his great escape, his life ended.

Safe, hidden, and almost anonymous, Benjamin was buried in the Pere Lachaise Cemetery — perhaps, just the way he had intended.

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