Red Jacket's birthplace has long been a matter of debate. Some historians claim he was born about 1750 at Kanadaseaga, also known as the Old Seneca Castle. Present-day Geneva, New York, developed near here, at the foot of Seneca Lake. Others believe he was born near Cayuga Lake and present-day Canoga, Others say he was born south of present-day Branchport, at Keuka Lake near the mouth of Basswood Creek. It is known that he grew up with his family at Basswood Creek, and his mother was buried there after her death. The Iroquois had a matrilineal kinship system, with inheritance and descent figured through the maternal line. Red Jacket was considered to be born into his mother's Wolf Clan, and his social status was based on her family and clan.
Red Jacket lived much of his adult life in Seneca territory in the Genesee River Valley in western New York. In the later years of his life, Red Jacket moved to Canada for a short period of time. He and the Mohawk chief Joseph Brant became bitter enemies and rivals before the American Revolutionary War, although they often met together at the Iroquois Confederacy's Longhouse. During the war, when most of both the Seneca and Mohawk were allies of the British, Brant contemptuously referred to Red Jacket as "cow killer". He alleged that at the Battle of Newtown in 1779, Red Jacket killed a cow and used the blood as evidence to claim he had killed an American rebel.
. Red Jacket met with presidents George Washington, and later John Adams, in the presidential mansion in Philadelphia, when that city was the temporary national capital.
Red Jacket became famous as an orator, speaking for the rights of his people. After the war, he played a prominent role in negotiations with the new United States federal government. In 1792 he led a delegation of 50 Native American leaders to Philadelphia. The US president George Washington presented him with a special "peace medal", a large oval of silverplate engraved with an image of Washington on the right-hand side shaking Red Jacket's hand; below was inscribed "George Washington", "Red Jacket", and "1792".
Red Jacket wore this medal on his chest in every portrait painted of him. (Today the medal is held in the collection of the Buffalo History Museum.)He was also presented with a silver inlaid half-stock long rifle, bearing his initials and Wolf clan emblem in the stock and his later name Sagoyewatha inlaid on the barrel. This rifle has been in private hands since his death.
In 1794, Red Jacket was a signatory, along with Cornplanter, Handsome Lake, and fifty other Iroquois leaders, of the Treaty of Canandaigua, by which they were forced to cede much of their land to the United States due to the defeat of their British ally during the war. Britain had ceded all its claims to land in the colonies without consulting the Iroquois or other Native American allies. The treaty confirmed peace with the United States, as well as the boundaries of the postwar the Phelps and Gorham Purchase (1788) of most of the Seneca land east of the Genesee River in western New York.
In 1790 Jemima Wilkinson, known as The Publick Universal Friend, and her Philadelphia Society of Friends were the first settlers in the formerly Seneca region. Despite the pillaging of the Native River-Settlement in Ah-Wa-Ga Oswego, New York, by generals Clinton and Sullivan during the Revolutionary War, the Society made peace with the wary Seneca tribe. Most of the Seneca, including Red Jacket, recognized the Universal Friend as Chieftain. The Seneca Tribe made peace with settlers in the Finger Lakes region, but they suffered hardship in the Genesee Region and other parts of Western New York.
In 1797, by the Treaty of Big Tree, Robert Morris paid $100,000 to the Seneca for rights to some of their lands west of the Genesee River. (This area developed as present-day Geneseo in Livingston County). Red Jacket had tried to prevent the sale but, unable to persuade the other chiefs, he gave up his opposition. As often occurred, Morris used gifts of liquor to the Seneca men and trinkets to the women to "grease" the sale. Morris had previously purchased the land from Massachusetts, subject to the Indian title, then sold it to the Holland Land Company for speculative development. He retained only the Morris Reserve, an estate near the present-day city of Rochester. During the negotiations, Brant was reported to have told an insulting story about Red Jacket. Cornplanter intervened and prevented the Seneca leader from attacking and killing Brant.
Red Jacket took his name, one of several he used as an adult, for a highly favored embroidered coat given to him by the British for his wartime services. The Seneca allied with the British Crown during the American Revolution, both because of their long trading relationships and in the hope that the British could limit colonial encroachment on their territory. After their ally lost, the Seneca were forced to cede much of their territory to the United States. Many of their people resettled in Canada at what is now the Six Nations Reserve in Ontario. In the War of 1812, Red Jacket supported the American side.
His later adult name, Sagoyewatha, which roughly translates as "he keeps them awake", was given by the Seneca about 1780 in recognition of his oratory skill. When in 1805 Mr. Cram, a New England missionary, asked to do mission work among the Seneca, Red Jacket responded by saying that the Seneca had suffered much at the hands of Europeans. His speech, "Religion for the White Man and the Red", expressed his profound belief that Native American religion was fitting and sufficient for Seneca and Native American culture. It has been documented and preserved as one of the best examples of North American oratory.
Red Jacket developed a problem with alcohol and deeply regretted having taken his first drink (see following quote). When asked if he had children, the chief, who had lost most of his offspring to illness, said:
- "Red Jacket was once a great man, and in favor with the Great Spirit. He was a lofty pine among the smaller trees of the forest. But, after years of glory, he degraded himself by drinking the firewater of the white man. The Great Spirit has looked upon him in anger, and his lightning has stripped the pine of its branches."
In his later years, Segoyewatha lived in Buffalo, New York. On his death, his remains were buried in an Indian cemetery (now within Seneca Indian Park in South Buffalo, New York). In 1876, the politician William C. Bryant presented a plan to the Council of the Seneca Nation to reinter Red Jacket's remains in Forest Lawn Cemetery, Buffalo. This was carried out on October 9, 1884. The proceedings, with papers documenting speeches given by Horatio Hale, General Ely S. Parker (Red Jacket's nephew's grandson, known as a "clan grandson," who inherited the famous medal), and others, were published (Buffalo, 1884). A memorial to Red Jacket still stands within Seneca Indian Park.
According to Appletons' Cyclopædia of American Biography, "Several portraits were made of him. George Catlin painted him twice, Henry Inman once, and Robert W. Weir did his portrait in 1828, when Red Jacket was on a visit to New York City. Fitz-Greene Halleck has celebrated him in song."