Red Jacket retreated at the approach of General John Sullivan (Sullivan, John)'s American troops in 1779, and he even attempted to conclude a separate peace with the Americans. For these actions, Red Jacket was considered a coward by many of his own people. But he put his splendid oratorical skills to protesting the inevitable peacemaking with the United States at an Indian council in 1786, and his oratory succeeded in sustaining him as a Seneca chief.

Red Jacket constantly sought to portray himself as a bitter enemy of the whites. Yet, while he publicly opposed land sales in 1787, 1788, and 1790, he secretly signed the property cessions to protect his prestige with the Americans. Later, however, he seems to have become more sincere in protesting white influence on Seneca customs, religion, and language. He vehemently opposed missionaries' living on Indian lands, and he vainly attempted to preserve Indian jurisdiction over criminal acts committed on Indian property.

During the 1820s Red Jacket lost prestige as his drinking and general dissipation became evident. In 1827 he was deposed as chief by a council of tribal leaders—only to be reinstated following a personal effort at reform and the intercession of the U.S. Office of Indian Affairs.