Osceola

This 1838 portrait of Osceola by George Catlin hangs in the National Portrait Gallery in Washington, DC.

"The Seminole Indians of the Southeast were directly affected by Andrew Jackson's policy of Indian removal, and although a portion of his tribe's leadership gave in to the federal government, Osceola led the resistance. Unlike Black Hawk, who fought the Americans in the West, Osceola did not take on the U.S. military in open battle, but conducted a campaign of guerrilla warfare, harassing federal authorities from the Seminole base in the Everglades. Osceola was captured after the Americans violated a flag of truce. He died in prison shortly thereafter, but the Seminole, famously, never surrendered to the United States." -- National Portrait Gallery

John Sartain produced this engraving of Catlin's painting.

Osceola by George Catlin, engraved by John Sartain

SAAM

Catlin painted Osceola during his capture at Fort Moultrie. Robert John Curtis painted him in the same period.

This portrait of  Asseola, a Seminole Leader, appeared in Thomas Loraine McKenney, History of Indian Tribes of North America, 1872.

Pe-o-ka

The portrait below known as the Sedgeford Portrait has been widely believed to be a picture of Pocahontas and her son Thomas Rolfe. Modern, 21st century, scholarship has concluded that it is a portrait of Pe-o-ka, one of Osceola's two wives, and their son.

(Wikipedia)

This old postcard (available on E-bay, in 2025) identifies the subjects as Pocahontas and Thomas Rolfe:

The Magazine of the National Museum of the American Indian, summer 2013, remarks:

Now that the true identity of this mother and child is known, this painting has gained greater historical importance and considerable interest. Historians possess almost no information on Pe-o-ka, and this portrait is the only known image of her. Her story as a widow and a mother is unknown.

See Pe-o-ka's own entry in the Portrait Gallery. 

Osceola's Grave

The National Register of Historic Places Nomination Form for Fort Sumpter/Fort Moultrie says:

While at the fort, Osceola became somewhat of a celebrity due to his personal bearing and sympathy for his capture under a truce flag. Already suffering from ill health, Osceola died from quinsy at the fort on January 30, 1838. His remains were buried there, but his head was removed secretly by Dr. Weedon, the army physician. The head was taken for study and later lost in a museum fire.

A Mr. Patten of Charleston, S. C. placed a stone marker on the grave with the inscription: Oceola (sic), Patriot and Warrier, Died at Fort Moultrie, January 30, 1838. In the late 1880's an iron fence was erected around the grave enclosing an area approximately 5' x 7'. 

 Harper's Encyclopædia has this image of Osceola's Grave at Fort Moultrie. 

Osceola's epitaph reads:

OCEOLA

Patriot and Warrior

Died at Fort Moultrie

January 30th 1838.

______________

Osceola's friend and physician Dr. Weedon displayed Osceola's head in his pharmacy in St.  Augustine.

On June 18, 1842 a correspondent styling himself  "A Dragoon" wrote to the New York Herald about the "scientific" decapitation of a Fiji Chief. He asked, perhaps rhetorically, "what has become of the head of the renowned Seminole Chief Osceola?" The next day another correspondent calling himself "3d Artillery" answered, "If  'A Dragoon' will take a trip to St. Augustine, (Florida) and look into the shop of Doctor W. he will see Osceola's head, preserved in pickle, in a glass vase."