Smallwood Starting in 1896 Ted Smallwood carried the mail by sailboat between Chokoloskee and Marco Island via Everglades [City]. In 1897 he married and settled down on Chokoloskee Island. He hunted alligators, cut buttonwood (for charcoal), fished, and raised tomatoes. In 1906 he became postmaster for Chokoloskee and opened a general store which housed the post office. He remained postmaster until he retired in 1941. His daughter succeeded him as postmaster. Ted Smallwood died in 1951, but his daughters kept the store open until 1982. Ted Smallwood's store was placed on the National Register of Historic Places in 1974. His granddaughter has opened the store as a museum. Edgar Watson The Ten Thousand Islands country, including Chokoloskee, had a reputation as being a refuge for outlaws. The Ed Watson story, as related by Ted Smallwood, is the best known example of that. Edgar Watson, a native of Ridge Springs, in the Saluda Division of Edgefield District, South Carolina, showed up in the Chokoloskee Bay country in the early 1880s. He had supposedly gotten into trouble in Columbia County in northern Florida, to which his parents had migrated sometime after 1870, and had then gone out to the Indian territory (later known as the Oklahoma Territory) where he allegedly killed Belle Starr, herself allegedly an outlaw. He then returned to Florida and killed a man in Arcadia, apparently in self-defense. After that Ed Watson moved to the Ten Thousand Islands area, then part of Monroe County, where he bought a claim on the Chatham Bend River and began raising vegetables. On a trip to Key West, Watson got into an argument with Adolphus Santini and tried to cut his throat. Santini survived, but the incident cost Watson $900. After that Watson bought a claim on the Lost Man's River, also in Monroe County. A man named Tucker soon squatted on the claim and would not leave. Eventually Tucker and his nephew were found murdered, and suspicion fell on Watson. After that Watson went back to Fort White, Columbia County. While there he again became involved with bad company, and came under suspicion in the deaths of two men. Watson returned to the Chatham Bend area and began making syrup from sugar cane. According to legend, Watson would "pay" his African-American and Native American help by killing them on payday. Soon Watson had several people living at his place, including a man