Osceola and his warriors were taken by their captors to St. Augustine where they were imprisoned within the strong walls of the old Spanish castle of San Marco. It was very hard for these Indians who loved liberty better than life to be shut up in narrow dark cells, to be obliged to give up the warpath, to sit for hours, and days, and weeks, and months in inaction, not knowing what need their friends had of them but imagining the heaviest possible misfortunes for those they held dear.

Osceola could have stood the torture of wrenched limbs and of fire with haughty spirit unbent. What was that to this torture of the white man's, the dim light, the quiet, the narrow walls, the waiting, the not knowing, the fearing of evil?

The warrior still held his head high, but gradually the fierce gleam in his eye changed to a look of gentleness, of unspeakable sadness, and his winning smile came to have so much sorrow in it that men said to each other after they left him, "His heart is breaking." He was allowed to see and talk with other prisoners. When Micanopy and other chiefs were brought to the fort he was told of their arrival. When Wild Cat, after fasting many days, escaped through the small window in his wall with the help of a rope made from his blanket, Osceola was aware of it. But none of these things seemed to move him.

General Jesup told the chiefs that he would urge the United States authorities to let them and their people stay in southern Florida if they would agree to keep their tribes at peace, guard the frontier, and themselves accompany him to Washington. Micanopy showed a little distrust when he heard the proposition, but Osceola took off his proud head dress and removing one of the beautiful plumes from it handed it to the man who had betrayed him, saying simply: "Give this to my white father to show him that Osceola will do as you have said."

The suggestion made by General Jesup was not considered favorably by the government, but he was instructed to carry out the Jackson policy of transportation. He had collected so many captives at St. Augustine that he feared trouble and decided to separate them. He sent all the negroes to Tampa and the Indians to Charleston, S. C. Late in December the Indians were shipped on the steamer Poinsett. Among them were Osceola, Micanopy, Alligator and Cloud. Besides the chiefs one hundred and sixteen warriors and eighty-two women and children were sent to Fort Moultrie. Osceola's two wives and little daughters were in the company. They arrived at Charleston on the first day of January, 1838, after a quiet voyage.

At Fort Moultrie, Osceola was treated with much consideration; he was allowed to walk about the enclosure and to receive visitors in his room. Still he ate little and every day grew more wan and thin. All the chiefs were so low-spirited that great efforts were made to cheer them. A very popular actress was then playing at the Charleston theater, and knowing the Indian's love of whatever is gay and spectacular, the authorities at the fort decided to take the chiefs to the theater on the sixth of January.

Public sympathy had been excited by reports of the capture, imprisonment, and failing health of the once terrible Osceola. The theater was crowded with Charleston people more anxious to see the chief than the beautiful actress. The Indians were led into the brilliantly lighted hall filled with staring men and women. They looked neither to the right nor to the left, but took their places in quiet and watched with steady eyes and unsmiling faces the entertainment provided for them. Osceola had made no objection to coming, but he sat amidst the mirth and glamor, so sad and stern that those who had brought him there and those who had come to see him felt rebuked. His trouble was too real to be easily comforted, too deep to be an amusing spectacle. The papers of the day recorded the strange scene of the captive Osceola at the play in poetry and prose.

Later an incident happened in which Osceola took some interest. George Catlin, who had traveled for several years among the Indians and was regarded by them as a friend, came to the fort to paint the portraits of the chiefs for the United States government. When Mr. Catlin asked Osceola if he might paint his portrait the latter seemed greatly pleased. He arrayed himself in his gayest calico hunting shirt, his splendid plumed turban, and all his ornaments, and stood patiently while the artist worked. Mr. Catlin enjoyed painting the fine head, with its high forehead and clear eye. He made two portraits of Osceola, both of which are now in the collection of Indian portraits at the Smithsonian Institution, in Washington.

Mr. Catlin came to be well acquainted with the chiefs whose portraits he painted, and used to have them come to his room in the evenings, where they all talked with great freedom. He felt deep sympathy for Osceola, who told him all the details of his capture. When Osceola learned that Mr. Catlin had been west of the Mississippi he asked him many questions about the country and the Indians living there.

But every day Osceola's health grew more feeble and, on the day when the second portrait was finished, he became so ill that he was thought to be dying. He rallied, however, and when Mr. Catlin left a few days later, it was with the hope that Osceola would regain his health and strength. He requested the fort doctor to keep him informed about the chief's condition.