
Guyasuta adopted Girty as his own son, raising him as befit a Seneca warrior. Simon used his time with the Seneca to learn the languages and customs of several Northeastern Woodlands tribes. In 1764, after Pontiac's Rebellion, the British demanded that all White captives be ransomed. Guyasuta released Simon at Fort Pitt. Simon would've sneaked back to the Seneca had he not been reunited with James and George, his two younger brothers. Thomas, the eldest, had escaped and returned to White society years earlier and John, Jr. was ransomed along with his mother. James, George and Simon traded on their skills with languages and as guides and hunters to make a living in what was to them now an alien society.
Simon was the best at interpreting. He was present at the negotiations for the Treaty of Fort Stanwix in 1768, and transmitted Logan's remarks at the end of Lord Dunmore's War. At the beginning of the Revolution he sided with the Colonists, angering Guyasuta, with whom he still kept in contact. As the War progressed and he saw how Natives were being treated, he defected to the British. As he wasn't in a military unit, it was a defection and not desertion, as is sometimes claimed. He became an employee of the British Indian Department with the rank and pay of captain.

As the Revolution wound down, in 1784, Simon spotted a pretty young woman who'd been captured by the Delaware. He ransomed her, proposed, and took her to Fort Detroit at her request for a religious marriage in her mother's presence. Catherine Malotte Girty would bear her husband five children and endure much separation from him during the Northwest Indian War, 1785-1795. As he grew older, Simon began to drink more heavily. While he might have developed a dependence on alcohol just due to its availability, there might have been more. He was beginning to suffer arthritis, had frequent headaches, and was described as having unpredictable moods. The drinking and long separations took their toll on his marriage. Catherine left him, dividing her time between Detroit and Simon's land in Amherstberg, Ontario. There is no evidence that she left because of domestic abuse.
After the end of the Northwest War in 1795, Simon was laid off by the Indian Department, though called back whenever they were shorthanded. As arthritis, depression and drinking took their toll, He was used less and less. While White society marginalized him, Natives, particularly the Mohawk and Shawnee, continue to consider him a friend. When Tecumseh passed through Amherstberg in 1813, he sought Simon out. Simon did not participate in the War of 1812, though his son Thomas died by heat exhaustion helping a wounded British soldier off a battlefield.
When American forces crossed from Detroit to Amherstberg Simon was forced to evacuate his farm and found shelter with Mohawks at the Grand River Reserve. His daughter-in-law, Thomas' widow, stayed to run the farm. While she was pleading with the soldiers not to burn down the only home for herself and her expectant child an older man intervened. It was Simon Kenton, who repaid his old friend Girty for saving his life. Monica gave birth to a baby girl and they welcomed Simon home.
Catherine realized the Simon was failing fast and needed help as his eyesight failed, his arthritis and gout increased and drinking was the only pain relief available. Simon lived out his remaining days on his farm in Canada, blind, crippled and forgotten by all except his family and a few Mohawk friends who were present at his bedside when he died.
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