Benjamin Chaires Sr. (1786–1838) was an American planter, land owner, banker and investor in Territorial Florida, and may have been the richest man in Florida in the 1830s. He was involved in the creation of the first railroads in Florida.
Early career
Benjamin Chaires was born in Onslow County, North Carolina in 1786. He lived in Georgia before moving to Florida. He had married, and become a surveyor and a plantation owner by the time he was 30.
Chaires started buying land in Florida while it was still controlled by Spain. He bought a one-third interest in a plantation on Amelia Island in 1818. He also bought land near Jacksonville and St. Augustine.
While living in northeastern Florida, Chaires was involved in a lawsuit with Zephaniah Kingsley involving timber Chaires had harvested from Kingsley's Greenfield Plantation. In May 1820, Chaires and Thomas Fitch purchased 59 slaves from George Atkinson of Camden County, Georgia, with Chaires receiving 32 of the slaves as his share.
The city of Jacksonville was founded in 1822, after Florida became a territory of the United States. The survey of the first section of Jacksonville was conducted in June 1822 under the supervision of Chaires and two other commissioners. Duval County was created out of St. Johns County on August 12, 1822, and Jacksonville was soon designated the county seat of Duval County. John Brady transferred a lot in trust to Chaires and Francis Ross as the site for a courthouse. After framing for the courthouse was erected on the lot, Chaires and Ross transferred the lot and partially constructed courthouse to the county. Chaires was friends with William Pope Duval, governor of the Florida Territory, who appointed Chaires County Judge for Duval County for a term in 1823–1824. Chaires was also a justice of the peace in Duval county.
In 1824, Chaires was the successful bidder to provide rations to the Seminoles as provided for in the Treaty of Moultrie Creek. He was among several prominent men in Florida who felt that the allocations by the government for the rations were not sufficient to support the Seminoles, in part because the lands included in the reservation were among the agriculturally poorest in the territory. Chaires recommended expanding the reservation to include better land. He held the contract for only a year, but the profits that he made from that contract partially funded his purchases of land.
Chaires acquired land across northern Florida. He eventually bought in St. Johns, Duval and Alachua counties. In 1829, a major part of a 20,000 acre Spanish land grant in what is now Columbia County, now known as the "Little Arredondo Grant", was transferred to Chaires. Along with his extensive lands near Tallahassee, he had large interests in the areas around St. Marks and St. Joseph. Sharyn Shields states that Chaires had purchased up to 45,000 acres in Florida.
Leon County
Chaires moved to Tallahassee in the late 1820s. He became one of the wealthiest land owners in Leon County. His brothers Green H. Chaires and Thomas Peter Chaires also established plantations in Leon County, Evergreen Hills Plantation and Woodlawn Plantation, respectively. In 1830, Chaires bought land on the north side of Tallahassee and built the house called The Columns. Chaires sold The Columns in 1832 and built the Verdura plantation house, which was reputed to be the finest in Florida, on ten miles east of Tallahassee that became the core of the Verdura Plantation.
Chaires and his brothers all had slaves on their plantations produce bricks by hand. Chaires used such bricks for the Columns and the mansion and outbuildings at Verdura, and he and his brothers supplied bricks for the Apalachicola Arsenal in Chattahoochee, Florida, the second state capital building in Tallahassee, and other buildings in Tallahassee.
Chaires owned other land in Leon County, as well as the Bolton Plantation in Jefferson County. In 1836 Chaires bought a plantation of 800 acres and 57 slaves with a price of $25,000 listed on the deed, but Chaires took out a $50,000 mortgage to pay for it. The discrepancy may represent an undervaluation of the sale for tax purposes.