Florida’s Gamble Plantation: where the Confederate Secretary of State cheated the gallows

Judah Benjamin’s Daring Escape Through Gamble Plantation

When Richmond fell in April 1865, Judah Benjamin faced a stark choice: capture or flight. As Confederate Secretary of State with a price on his head, he split from Jefferson Davis and headed for Florida.

At Gamble Plantation, he hid from Union patrols, twice escaping to nearby woods when soldiers searched the mansion.

Later, he sailed from Sarasota Bay disguised as a ship’s cook, his face smeared with grease to fool inspectors.

After a perilous journey through the Bahamas, Benjamin reached England where he built a new life as a respected lawyer.

The Gamble Plantation still stands today, preserving the dramatic story of America’s highest-ranking Jewish official and his daring escape.

Richmond Fell and the Confederate Leadership Scrambled South

Judah P. Benjamin burned secret papers in Richmond on April 2, 1865, before running away with President Jefferson Davis.

Benjamin was the highest-ranking Jewish official in American government history and worked for Davis in three jobs: Attorney General, Secretary of War, and Secretary of State.

Union forces put a big reward on his head, blaming him for helping kill Lincoln. If caught, he faced a treason trial.

The Confederate leaders headed south toward North Carolina with $500,000 in Confederate gold, hoping to set up their government somewhere else.

Breaking Away From Davis Changed Benjamin’s Escape Plan

On May 3, 1865, near Washington, Georgia, Benjamin told President Davis he couldn’t handle the tough journey anymore. He asked to try escaping through Florida instead of continuing their hard overland trip.

Benjamin knew Union spies had already warned troops about Confederate leaders possibly using Florida to escape. His timing was good.

Just one week later, on May 10, Union soldiers caught President Davis and his remaining cabinet in Irwinsville, Georgia, while Benjamin was already heading toward Florida’s coast.

Fake Names and Disguises Helped Him Enter Florida Undetected

Benjamin first pretended to be a Frenchman named “M.M. Bonfals” (meaning “good disguise”) with a full beard, hat, goggles, and cloak.

He entered Florida through Madison County using a Confederate passport before switching to act as “Charles Howard,” a farmer from South Carolina. Union forces watched several Florida rivers and ports.

Benjamin crossed the Suwannee River on May 14, 1865, two weeks after leaving Davis’s group.

His Week in Brooksville Brought New Plans and Clothes

Benjamin got to Brooksville around May 19, 1865, still acting like a farmer looking for land. He dropped his plan to reach Indian River after learning there weren’t enough boats and the east coast was too risky.

A local farmer and his wife gave Benjamin homemade clothes and basic gear for his horse. He spent about a week in Brooksville making friends with people who backed the Confederate cause.

Storms Covered His Journey to the Gamble Plantation

Captain Leroy Lesley from Brooksville and Captain James McKay from Tampa moved Benjamin south during a big storm.

They took him to the Gamble Plantation in Ellenton, owned by Captain Archibald McNeill, who ran goods through Union blockades.

The mansion was the only standing plantation house in peninsular Florida, built with thick walls that gave good shelter. McNeill agreed to hide the wanted Secretary of State despite the big risks.

Federal Troops Almost Found Him at the Mansion Twice

Benjamin hid at the plantation during May 1865 while McNeill worked on escape plans. When federal troops suddenly came to the mansion, Benjamin ran to hide in the nearby woods twice.

Union soldiers looked for him during their searches after getting tips about Confederate officials using Florida escape routes. After nearly a week of close calls, Benjamin’s helpers decided to move him somewhere safer.

Captain Tresca’s Home Became His Next Hiding Spot

Benjamin moved to Captain Frederick Tresca’s home in Bradenton on the Manatee River for about a month. Tresca, born in France, knew every part of the coast between Cedar Keys and Key West.

Hiram McLeod, who knew local waters and roads, helped plan the escape. Benjamin stayed hidden on the second floor while the group figured out details for his sea trip.

They needed a boat, supplies, and a safe route away from Union patrols.

Fresh Beef and Palmetto Leaves Concealed His Final Land Journey

Tresca found and bought a sixteen-foot boat at Clearwater using Benjamin’s money. Ezekial Glazier drove a wagon from Tresca’s home to William Whitaker’s house in Sarasota.

Benjamin hid under fresh beef covered with palmetto leaves during this risky final land trip.

Mrs. Whitaker cooked a big goodbye dinner while others got the boat ready with supplies at Yellow Bluffs. The group knew this would be Benjamin’s last meal in America for a long time.

The Tiny Sloop Left Sarasota Bay on a Dangerous Mission

On June 23, 1865, Benjamin, Tresca, and sailor H.A. McLeod sailed from Sarasota Bay in their small open boat.

The Whitaker family watched from Yellow Bluffs as the boat slowly moved down Sarasota Bay through the pass. Benjamin now faced the most dangerous part of his escape, with Union navy patrols and rough Gulf waters ahead.

Their small vessel carried lots of supplies for what turned into a hard two-week trip through changing waters and weather.

Grease and Soot Transformed Him into a Ship’s Cook

Benjamin disguised himself as the ship’s cook, wearing an apron and smearing his face with grease and soot to avoid recognition.

When Union soldiers checked their vessel, one remarked it was the first time he’d seen a Jewish man doing menial labor, not realizing he was looking at the Confederate Secretary of State.

The group faced waterspouts, leaky boats, and several near-disasters during their journey. They finally reached Knight’s Key on July 7, where Benjamin got on another boat heading for Bimini.

England Became His New Home After Reaching the Bahamas

Benjamin safely arrived in Bimini on July 10, 1865, completing his dramatic escape from Union forces. His journey continued with shipwrecks and fires before he finally reached England on August 30, 1865.

In England, Benjamin rebuilt his legal career using money from cotton bales he had shipped earlier.

He became Queen’s Counsel in 1872, the highest rank for lawyers in England, and never returned to the United States despite later being granted amnesty. He died in Paris in 1884 at age 72.

Visiting Gamble Plantation Historic State Park, Florida

Gamble Plantation Historic State Park at 3708 US Highway 301 East in Ellenton tells the story of Confederate Secretary Judah P. Benjamin’s dramatic 1865 escape.

You can tour the mansion where Benjamin hid from Union forces for $6 adults/$4 children, with tours running six times daily from 9:30am to 4pm.

The visitor center opens Thursday through Monday 9am-5pm with a lunch break. Park entrance is free and picnic tables are behind the mansion.

This article was created with AI assistance and human editing.

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