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Lappawinsoe was a Lenape-Delaware chief. His name, often spelled as Lappawinzo, Lapowinzo or Lapowinsa signifies "gathering fruit" or "going away to gather food".

He sold the land of his tribe to Thomas Penn, the son of William Penn, through the Walking Purchase agreement. Three other Lenape-Delaware chiefs also signed the agreement: Tishecunk (sometimes refered to as Tishcohan, "tash-suk-amen" meaning "he never blackens himself"), Nutimus ("striker of fish with a spear") and Menakihikon ("a King of the Minissincks"). Documentation shows that Nutimus was considered the principal Indian leader of the tribes located in Delaware.

Portrait
Historians such as Marshall Becker have credited Lappawinsoe as the first Native American to be portrayed in an oil painting. Lappawinsoe and Tishecunk are considered "the only two chiefs of the Lenni Lenape whose portraits have been preserved". In his portrait, Lappawinsoe is shown as a muscular man of about 40 years of age. Further descriptions of the painting focus on the tattoos on Lappawinsoe´s face and neck as well as on the pouch he is wearing. The pouch is compared to the one worn by Tishcohan in his respective painting. The tattoos on Lappawinsoes forehead symbolize two thunderbirds and a snake or serpent. Body tattoos are used to represent information about the person´s character and their beliefs. The Thunderbird is considered a "powerful spirit being" and signifies an "active and swift-footed warrior".

Walking Purchase Agreement
In 1737, Lappawinsoe signed the Walking Purchase agreement to sell part of his tribe´s land "extending as far west as a man could walk in a day and a half". An attributed quote states: "Chief Lappawinsoe, believing the treaty genuine and assuming a man could only walk 40 miles, agreed to the WALK!". William Penn´s sons, Thomas Penn and John Penn, convinced the Lenape that their father had already bought the land from them. Contrary to Lenape believe, Thomas Penn, John Penn and James Logan hired fast runners to run a prepared path which resulted in a bigger landloss for the Lenape than they had imagined. Edward Marshall, one of the three walkers and the only one who completed the full walk, states in a testimony in 1751 that Lappawinsoe was living in the Indian town Hockendocqua (also referred to as Hociundoquen). When he was passing the place during the walk asking Lappawinsoe for an Indian to come with him, he said "they had got all the best land, and they might go to the Devil for the bad" and that he would send no Indian with them. Furthermore, Lappawinsoe is said to have described the walk as not "fairly performed" and "no sit down to smoke, no shoot a squirrel, but lun, lun, lun all day long!"

The Lenni Lenape had a friendly relationship with William Penn, including several fair treaties they made with him. Over the years, this lead to a good reputation of the Pennsylvania government among the Lenape people. Part of the reason the Lenape chiefs signed the Walking Purchase treaty was also to honor this peaceful relationship with William Penn.