Divided warpaths

William Tecumseh Sherman and Coacoochee
In 1841, William Tecumseh Sherman played a leading role in capturing the Seminole nation’s most dangerous leader, Coacoochee, in Fort Pierce.

One veteran of the Second Seminole War was the victor, the other became the vanquished


Micanopy, the Seminole nation’s leading chief during the Second Seminole War, was Coacoochee’s uncle. LIBRARY OF CONGRESS

Everyone has heard of Osceola, but how about the Seminole warlord who replaced him during the Florida War? Coacoochee was his name and the safest prison in the peninsula couldn’t hold him. Not for long. He was just as dangerous, just as dashing, just as fiercely brilliant as Osceola — even more so. As the chief opponent of the 1830 Indian Removal Act, no place in Florida was safe for soldiers and white settlers while Coacoochee was running free.

He and his devoted warriors could be lying in ambush within every thicket, along any trail, behind any clump of trees. It is one of history’s ironies that a future Yankee warlord famous for his own brand of terror, William Tecumseh Sherman, would play a key role in bringing Coacoochee’s reign to an end — right here on the Treasure Coast.

According to his biographer Susan A. Miller, a scholar of Seminole descent, his name should be pronounced CoAHcoochee or GoAHgoojee. That takes some getting used to, so many historians have taken the easy way out and resorted to calling him Wild Cat, based on a loose translation of his Seminole name.

History’s victors tend to run roughshod over some of the finer details of yesteryear’s reality. For instance, as Miller tells us in her book Coacoochee’s Bones, Osceola’s name wasn’t really Osceola. It was Asin Yahola, but a mispronunciation caught on with the public and became a permanent part of his legend.

The Florida War, also known as the Second Seminole War [1835-1842], began in earnest when the Seminoles made coordinated attacks in several regions. Coacoochee’s first assignment was to wipe out nearly every large sugar plantation on the east coast of Florida. He took scalps, liberated black slaves who joined him and burned everything to the ground.

His warriors even tore up the lighthouse at Ponce de Leon Inlet near New Smyrna, and soon thereafter, Coacoochee was seen wearing one of the shiny lighthouse reflectors as part of his flamboyant outfit. He became famous for outlandish attire. Most notably, he ambushed a group of Shakespearean actors on a road near St. Augustine and stole their costumes. He sometimes dressed as Hamlet after that.

No less than 16 plantations along the east coast of Florida, including sugar mills and cotton gins, were destroyed by Coacoochee and his father’s warriors. Some of the ruins still exist today and can be found in places like New Smyrna Beach. RICK CRARY

President Zachary Taylor
President Zachary Taylor was one of the powerful politicians who attended young Sherman’s wedding in 1850. LIBRARY OF CONGRESS

While Coacoochee was busy clearing hutkes [white settlers] out of Florida in 1836, the future American warlord who would capture him five years later was still a 16-year-old orphan in Ohio. Ironically named for one of history’s greatest Native American leaders, William Tecumseh Sherman — better known to family and friends as “Cump”— received an appointment to the U.S. Military Academy at West Point.

Of course he had no idea that his first assignment after graduation would send him to the lonely outpost at Fort Pierce. Nor did anyone foresee the war driving the great Seminole leader to the Treasure Coast to make one last play for time.

Coincidentally, both Sherman and Coacoochee had major political connections within their respective cultures. Coacoochee was the young nephew of the Seminole nation’s leader, Micco Nuppa [Micanopy], and his father, Emathla [King Philip], was a highly regarded leader of the Seminoles living in the St. Johns River region. In essence, within the bounds of the Seminoles’ complex social order, Coacoochee was born to royalty, which Osceola was not.

Sherman’s foster father [and later his father-in-law], Thomas Ewing Sr., was one of the most powerful politicians in Washington — first as a senator and then as a member of the cabinet in three presidential administrations. That’s how young Cump got his appointment to West Point. It’s also the reason why, when he later married Ewing’s daughter, Ellen, in 1850, President Zachary Taylor attended Sherman’s wedding, along with other icons of American history like Daniel Webster and Henry Clay.

But Sherman’s powerhouse connections got him nowhere militarily for more than 20 years. The career soldier missed every bit of fighting until the Civil War broke out in 1861. Until then, his confrontation with Coacoochee at Fort Pierce was the biggest thing of historical import that ever happened to him.

Fort Marion
Imprisoned in Fort Marion early during the war, Coacoochee made a daring escape and continued to lead his warriors for several more years. RICK CRARY

At the time of their encounter, Coacoochee was already famous nationwide via newspaper accounts. In the 1836 book, Notices of Florida and the Campaigns, Myer M. Cohen, a young staff officer, described what it felt like to be on the receiving end of one of Coacoochee’s surprise attacks. After weeks in the wilderness with nothing happening, the soldiers became lax and some of them wandered away from camp without any weapons.

“What a scene presents itself!” Cohen wrote in his published journal. “A half hundred hideous, copper-colored savages, some dressed most fantastically and frightfully; others half-clad with hunting shirts; the rest naked; all with glaring eyes, black hair, and red-painted faces; jumping and screaming like insensate brutes, looking like gaunt and famished wolves thirsting for blood and springing on their prey. Our unarmed men hurrying towards camp, bleeding, falling, dying!”

Gruesome accounts of ambushes filled the public with terror, and yet, as with pirates, bank-robbers and other outlaws, there was fascination, too. It is an oddity of the Florida War that notorious Seminoles could come into forts and camps and even towns like St. Augustine during periods of truce to get free whiskey and other supplies.

The official policy of the United States was to coerce the Seminoles into choosing to move out West voluntarily. A combination of getting them hooked on products they craved and needed, plus making life in Florida otherwise too uncomfortable to stay, seems to have been the strategy early on.

Gen. Thomas S. Jesup
Gen. Thomas S. Jesup was the first to capture Coacoochee. He became the Seminole leader’s biggest supporter in Washington after the war. FLORIDA MEMORY

During truces, Gen. Thomas S. Jesup became acquainted with Coacoochee while Osceola was still very much alive and in the field.
In a letter dated April 9, 1837, Jesup wrote to the Secretary of War: “Co-a-co-chee is the son of Philip, the principal chief on the St. Johns River.

His influence is greater than that of his father. He is decidedly the most talented man I have seen among the Seminoles, and should, and no doubt will, be the principal Chief of the Nation.”

Capt. John T. Sprague, the army’s main compiler of intelligence concerning the Florida War, later described Coacoochee as “by far the most dangerous chieftain in the field. War to him was a pastime. He became merry by the excitement, and more vindictive and active by its barbarities...”

Those were characteristics that would one day apply to the conqueror Sherman, when he opted for total war against civilians in the towns, cities and countryside of the South.

One of the best glimpses we have of the marauding guerilla tactician and his baffling popularity with his enemies came when Coacoochee was the star guest at a grand party thrown by Brig. Gen. J.M. Hernandez in St. Augustine. There were 60 ladies in attendance according to army surgeon Samuel Forry. On Oct, 19, 1837, Forry wrote to a friend the day after the waltz:

“Coacoochee was the lion of the night, attracting the special attention of the ladies. He has the countenance of a white man — a perfect Apollo in his figure — dresses very gaudily, and has more vanity than a woman.”

Forry went on to report that the famous Seminole leader was so inebriated he needed two men to hold him upright. All the while he “continued to receive the applause of the ladies.”

Days after that big party, Jesup grew weary of delayed and broken promises of surrender. He seized Coacoochee, Osceola and other leading Seminoles while they were still under a white flag of truce. He had them imprisoned in Fort Marion [now known as Castillo de San Marco].

Osceola became sick and subsequently died in captivity, but Coacoochee escaped. According to legend, the Seminole leader starved himself down to a size skinny enough to crawl through a narrow air hole high at the top of his dungeon cell. Jesup was about the only person in America who never bought that story. He suspected the getaway — which included at least 17 other Seminole captives — had been an inside job.

Coacoochee’s forces joined in the effort to turn Col. Zachary Taylor’s troops back at the Battle of Okeechobee. RICK CRARY

As soon as he was free, Coacoochee summoned his warriors and hightailed it to the swamps around Lake Okeechobee, just in time to block an invasion into southeastern Florida by a future president’s troops.

It was Christmas Day 1837. As usual, the Seminoles played the field to their advantage and forced the soldiers to wade through reeds and bogs. After sustaining heavy casualties, Col. Zachary Taylor declared victory and retreated. Thanks to Coacoochee, the war would drag on for years — long enough for Sherman to graduate in 1840 as a 2nd lieutenant and join the war effort.

By the time Sherman arrived in Fort Pierce, Coacoochee had been reduced to playing hide and seek with the army for a couple of years. He must have been running low on gunpowder and bullets. He was also running out of places to hide where his people could stay long enough to raise needed crops without the army finding and destroying them.

When he showed up six miles west of Fort Pierce in 1841, no one seems to have realized that he had moved his women and children to a secret location on the Treasure Coast. It was somewhere out in the high ground nestled in the midst of “Al-pa-ti-o-kee Swamp,” as the military map designated the vast region.

An African American interpreter named Joe arrived at Fort Pierce on an Indian pony along with several other Seminoles. Joe showed the fort’s commander, Maj. Thomas Childs, a pass that had been negotiated with another officer elsewhere in the territory. Was it valid? Could the infamous Coacoochee safely come in for supplies? Childs said he could and gave Sherman the biggest assignment of his career before Lincoln offered him a command some 20 years later.

Childs ordered the 21-year-old lieutenant to ride into the wilderness and escort the Florida War’s most dangerous warlord back to the fort. Sherman chose 10 men to ride with him as a show of force.

For the first couple of miles as he rode beside Joe, Sherman was fairly sure he would be OK. His memoirs of decades later only give the smallest hint of what was running through his mind. Treachery is what he said he began to suspect. By treachery he meant ambush, and ambush meant he must have been thinking of gruesome ways so many others had died. Of course, the young officer must have been scared.

But Sherman wrote his recollections of his encounter years after his successes at Shiloh, Corinth, Meridian and Atlanta. It was after he became the scourge of Georgia’s civilians with his March to the Sea “to make them howl.”

It was after he burned down all those stately plantations all the way through the Carolinas, like Coacoochee burned down Florida’s finest. But after Sherman had dodged so many bullets and the murderous glares of thousands, what could he remember of the fears of that young man he was before he became America’s icon of total war? He only recorded a glimpse.

destroying parts of Atlanta
Sherman, who started his military career during the Second Seminole War, went on to lead Union soldiers, seen destroying parts of Atlanta, during Sherman’s celebrated March to the Sea.

According to his memoirs, Sherman found Coacoochee’s little camp beside a pond. There were 15 or 16 warriors, but Sherman couldn’t tell them apart. Where was the famous marauder? None of them really stood out. Then a man he described as young and handsome, but otherwise seemingly ordinary, approached his horse.

“Me Coacoochee,” he announced as he slapped his chest.

Coacoochee told Sherman to get off his horse. He wanted to sit down and talk. Sherman refused. The young lieutenant said that any talk would have to be with the “big chief” back in the fort, meaning Childs. Seeing the Seminoles’ rifles stacked against a tree nearby and sensing possible danger, Sherman ordered his men to take control of the guns. That made Coacoochee mad. Sherman calmed him down with assurances that the guns would be returned, plus a nice horse would be provided to him for the ride into Fort Pierce.

Coacoochee took his own sweet time after that, stripping down and bathing himself in the pond. Afterward, he ceremoniously dressed in his finest attire, which included buckskin leggings, moccasins, a number of shirts, and several vests — the last of which had a big bullet hole in the chest surrounded by a bloodstain.

“In due time,” Sherman added facetiously, “he was dressed with turban and ostrich feathers, and thus we rode back together to Fort Pierce.”

conceptual display of the old fort at Fort Pierce
This conceptual display of the old fort at Fort Pierce is one of the exhibits at the St. Lucie County Regional History Center. RICK CRARY

With his casual recollection of that striking scene, Sherman glosses over its greater significance, which we can elicit now. Two warlords riding side by side not knowing that history was watching — one present, one future — and more alike than either could imagine. They had yet to learn where destiny would take them.

Coacoochee spent the night in Fort Pierce, and in exchange for the umpteenth promise of surrender he acquired his needed supplies — except for bullets and gunpowder which he reportedly tried to finagle from some of the privates. Sherman noted that the famous chief got “regularly drunk” on commissary whiskey. Then he rode off the next morning, but some of his warriors returned repeatedly in the following weeks to gather more supplies.

After a month, Coacoochee returned but not with the promised numbers of his people. Instead, he brought 20 warriors with no intention to surrender. According to the Charleston Daily Courier, he came to invite the officers into the wilderness to celebrate the Green Corn Dance, the Seminoles’ most significant festival.

What he really had in mind, no one ever disclosed. But Childs had his suspicions. He directed Sherman to wait until the Seminoles were drunk and then seize them. The tension of timing the double-cross just right and the suspense of possible reactions must have all melted away when the plan was carried out with ease. They clamped them all in irons.

hammock west of Fort Pierce
This hammock west of Fort Pierce is reminiscent of the countryside through which Sherman and Coacoochee once rode side-by-side. RICK CRARY

That was the end of Coacoochee’s cherished years in the land of his birth. Heavily manacled on a prison ship in Tampa Bay and threatened with hanging, he sent for his followers. To save his life they joined him on a forced exodus.

After they arrived out west, he was unhappy with the treatment his people received on the reservation. So he traveled with a delegation to Washington, D.C., to complain that the government had failed to keep its promises. His first captor, Jesup, who by then was quartermaster general, took up his cause and lobbied on the Seminoles’ behalf to get their situation improved.

Life under the federal government’s dominion was still far from the great Floridian’s liking, so he moved his followers down through Texas and into Mexico, where Mexican authorities made him a better offer. In exchange for a bountiful helping of territory placed under his control, Coacoochee agreed to police the border with America. As leader of a colony, he became an officer in Mexico’s military. The Mexicans called him Capitán Gato del Monte [another loose translation of his name].

Fort Christmas Historical Park in Orange County
Fort Christmas Historical Park in Orange County features a full-scale replica of the fort built during the Second Seminole War in late 1837. The structure looks much like the fort along the Indian River in Fort Pierce would have looked in 1841. RICK CRARY

Ulysses S. Grant
Ulysses S. Grant and Sherman supported one another through desperately trying times. President Grant made Sherman America’s top general. LIBRARY OF CONGRESS

And Sherman? Sherman languished in more lonely outposts for what seemed to him like forever, according to his many letters home. Itching for action, desperate for fame, he finally gave up and tried to make a go of civilian life. He mostly failed.

When America split in two, his political connections finally came through. After a rocky start, he was given an endless supply of forces for a scorched-earth war of attrition. The grim, unyielding Sherman, more than anyone except for Gen. Ulysses S. Grant, forced a divided nation back into its uneasy alliance. But he never received the credit he should have earned for reuniting America.

History stresses Gen. Robert E. Lee’s surrender to Grant at Appomattox, but who celebrates the concluding event at Bennett Place in Durham, N.C.? That’s where Sherman negotiated the final surrender of Confederate forces after Lincoln’s assassination.

But he offered the Southerners such magnanimous terms, he was accused of treasonous intent by Secretary of War Edwin M. Stanton and the Northern press. After all he had risked to make his country whole, being called a traitor did not sit well with the proud conqueror. Sherman publicly threatened his superiors in the War Department and waged his politics like his war; he’s remembered for making it hell.

When Grant became president, he appointed Sherman the top general in the nation. That meant Native Americans standing in the way of railroads and progress were going to continue to have a hard time.

Coacoochee’s secret island hideaway in Central Florida
Coacoochee’s secret island hideaway in Central Florida was his safe retreat for most of the war, until a Native American betrayed its location. Although surrounded by conurbation, the area is still very hard to reach. RICK CRARY

And yet in the end, he did have some regrets about the way the Seminoles were treated.

“Indeed, Florida was the Indian’s paradise,” Sherman wrote in the 1885 revised edition of his memoirs, “…and it was a great pity to remove the Seminoles at all, for we could have collected there all the Choctaws, Creeks, Cherokees, and Chickasaws, in addition to the Seminoles. They would have thrived in the peninsula…”

Those sentiments came much too late for Coacoochee to hear or reflect upon —and most certainly lament. The Seminoles’ charismatic leader died in exile during a smallpox epidemic in 1857. As reported in The New York Times more than 30 years after his death, when once asked how he liked his new home, Coacoochee responded: “I have no home. Florida, which I love, was my home, but it is no more.”

See the original article in the print publication

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