If John Scott (1634?-1696) had his way, Long Island would have been the 14th colony and he its lord and ruler.

Instead, he has gone down in history as, at best, a wheeler-dealer and a mischief-maker and, at worst, a scoundrel with the dubious title of "America's first big-time swindler."

At least two books and numerous articles have been written about Scott, some hailing him as a hero of sorts — brash but brilliant — others condemning him as a despicable double dealer. Because he gave varying accounts of himself, his origins are murky. It is known he was born in Kent, England, to staunch Royalists and was an outlaw by the age of 10. When anti-Royalist forces stopped at a tavern, young Scott cut the bridles of their horses, an offense for which he was ultimately banished to Salem, Massachusetts, and placed as a bound boy with a Quaker family.

That delicious detail is found in a 1997 column by the late East Hampton historian Sherrill Foster. The bit about the bridle-slashing is not mentioned in Wilbur C. Abbot's 1918 essay on Scott, though he does confirm Scott's passage to America as a bound boy. According to Foster, in 1654 Scott went to sea as a buccaneer, a canny career move that gained him a fortune, thus enabling him to begin bigtime land dealing.

He acquired large tracts of land elsewhere on Long Island but there is general agreement that the late 1650s found him in Southampton working as a blacksmith, raising cattle, and perhaps, as Foster suggests, increasing his fortune by trading out of North Sea's busy port.

"He seems to have passed the next few years in the pursuit of a more or less honest livelihood," wrote Abbott with some amazement, though it wasn't all shoeing horses, tending cattle and bills of lading. Land speculation was an ongoing passion, as was his avid pursuit of the lordly life. He was made a freeman of Southampton, married Deborah, a daughter of Joseph Raynor of Southampton, and fathered two children who were born in their "manor" at North Sea. Scott was also appointed town tax commissioner, a post that allowed him to "correct" town boundaries and appropriate a large tract for himself, which he then sold to the town "at a considerable price," according to Foster.

From that coup, he went on to bigger things. Sometime near the end of 1660, he set sail for England, where he managed to meet with King Charles II, who was apparently seriously considering declaring Long Island a separate colony with "Captain" Scott as its governor. That didn't work out but, possibly as a consolation prize, he was appointed a magistrate for Long Island by Governor Winthrop. Eventually he overstepped, proclaiming himself president of Long Island, whereupon he was called to Hartford to explain himself and was promptly jailed by the governor.

Scott may have made some bad decisions in life but his choice of a wife was extraordinarily wise. Deborah, pregnant again, tucked a coil of rope under her dress and sailed off to rescue her husband from his third-floor prison cell. The maneuver succeeded and Scott hightailed it to Barbados, leaving wife and children behind. In 1681, Deborah obtained a divorce and married the very respectable Charles Sturmey of North Sea but when he died in 1691, the grieving widow lost little time in setting off for Barbados to rejoin the indomitable John Scott.

Sources from the Southampton Historical Museum: "'Colonel' John Scott of Long Island," essay by Wilbur c. Abbott; "The Arch Mischief Maker, John Scott," column by Sherrill Foster, The Independent; "America's First Big-Time Swindler," column from the files of Paul Bailey, edited by Carl A. Star ace, Suffolk County News.