Oliver Phelps (1749 - 1809) was born in Windsor, Connecticut and moved to Suffield, Connecticut, where he apprenticed to a local merchant. He later became a tavern keeper in Granville, Massachusetts. During the Revolution he became Deputy Commissary of the Colonial Army. He supplied troops and was commended by General George Washington. The connections he thus established aided his efforts in forming in 1789 a syndicate with Nathaniel Gorham. They purchased most of western New York from the state of Massachusetts. See: Phelps and Gorham Purchase.
At first they thought to make (modern day) Geneva their headquarters, but discovered by survey, just in time, that their site was just east of their boundary. So they chose Canandaigua, at the head of Canandaigua Lake, as the seat of the new Ontario County. The name Canandaigua is derived from the Iroquois word "Kanandarque" which means "chosen spot." It was the site of the principal village of the Seneca Indians, burned during the war in the Sullivan Expedition.
After the purchase, Phelps returned to Suffield, bought the Hatheway House, and opened a land sales office in Suffield, Connecticut and another in Canandaigua. He was appointed the first judge of Ontario County (1789 - 1793), even before he moved there. He built the first framed house in Canandaigua in 1792 then built a mill. Phelps retained extensive holdings in the infant Ontario County. He maintained an interest in its affairs — and in further land speculations. He was elected First Judge of Ontario county (1789-1793).
Despite vast land holdings that were worth a fortune, changing money values on mortgages held on the tracts of land sold and a depressed land market caused Phelps to get into financial difficulty. In about 1800, the reverses forced him to sell his Suffield home and his interest in the Hartford National Bank and Trust Co. Phelps moved to Canandaigua, N.Y., where he built a grist mill and endowed an academy. He was appointed the first judge of Ontario County.
After additional entanglements in western real estate ventures which resulted in "personal embarrassment" and, for a time, the prospect of debtor's prison, Phelps settled down in Canandaigua in 1802. He served in Congress from 1803 to 1805.
His troubles were not over, however. Purchasers of his land had continued difficulty paying off the mortgages which he held. He was generous in extending terms to them, to his own detriment. Phelps died in 1809 in debtors prison in the town he sold and helped develop.
This article is based in part upon material originally written by Brian Phelps and licensed for use in Wikipedia under the GFDL.