Benjamin Chaires

Benjamin Chaires Sr.
Born	1786 Onslow County, North Carolina, U.S.
Died	1838
Occupation(s)	Planter, landowner, banker, investor
Known for	Wealthiest individual in Florida during the 1830s; development of Florida's first railroads; president of Central Bank of Florida and railroad companies

Benjamin Chaires Sr. (1786–1838) was a prominent American planter, landowner, banker, and investor active in the Florida Territory, widely regarded as potentially the wealthiest individual in Florida throughout the 1830s. He significantly contributed to the development of Florida’s inaugural railroad systems.

Early career

Chaires was born in 1786 in Onslow County, North Carolina and initially resided in Georgia before moving to Florida. By the time he reached 30, he had married and established himself professionally as both a surveyor and plantation proprietor.

During the period of Spanish governance in Florida, Chaires started purchasing land, acquiring a one-third share of a plantation on Amelia Island in 1818, along with additional estates near Jacksonville and St. Augustine. While operating in northeast Florida, he became involved in a timber rights dispute with Zephaniah Kingsley. In 1820, together with Thomas Fitch, he bought 59 enslaved individuals from George Atkinson of Georgia; Chaires received 32 of them.

After Florida became a U.S. territory, Chaires took part in the first survey of Jacksonville in June 1822 with two commissioners. When Duval County was carved out from St. Johns County later that August and Jacksonville was designated its county seat, Chaires and Francis Ross acquired land intended for a courthouse site, which they eventually transferred to the county after partial construction had begun. A trusted ally of Governor William Pope Duval, Chaires served as Duval County Judge from 1823 to 1824 and also held the position of justice of the peace.

In 1824, Chaires obtained the contract to provide rations to the Seminole people under the terms of the Treaty of Moultrie Creek. He publicly criticized government provisions as inadequate due to the poor quality of reservation lands and advocated for expanding reservation boundaries. Though his contract lasted only one year, profits earned helped finance further land purchases.

Over time, Chaires accumulated vast tracts across northern Florida, ultimately controlling roughly 30,000 acres spanning St. Johns, Duval, and Alachua counties. In 1829, he acquired a substantial portion of the 20,000-acre "Little Arredondo Grant" located in what is now Columbia County. His portfolio also included large estates near Tallahassee as well as around St. Marks and St. Joseph. Some estimates place his total land acquisitions statewide at up to 45,000 acres.

Leon County

In the late 1820s, Chaires relocated to Tallahassee and emerged as one of Leon County’s most affluent landowners. His brothers—Green H. Chaires and Thomas Peter Chaires—founded Evergreen Hills and Woodlawn Plantations respectively. In 1830, Benjamin Chaires purchased property north of Tallahassee where he constructed The Columns. He sold this residence in 1832 and subsequently developed the Verdura plantation house approximately ten miles east of Tallahassee; this estate became central to what was known as Verdura Plantation.

Chaires and his siblings employed enslaved laborers who handmade bricks used not only for The Columns and Verdura’s buildings but also for prominent local structures such as the Apalachicola Arsenal, the second state capitol building in Tallahassee, among others.

Beyond his holdings in Leon County, Chaires possessed the Bolton Plantation situated in Jefferson County. In 1836, he acquired an 800-acre plantation along with 57 enslaved workers for $25,000 but arranged a mortgage totaling $50,000—likely an effort to reduce taxable valuation.

Banking and Railroad Ventures

Although Benjamin Chaires primarily concentrated on cotton farming, he was also deeply engaged in the banking sector and railroad enterprises. He held the position of president at the Central Bank of Florida, which was founded in Tallahassee in 1832. This institution expanded by acquiring the Bank of Florida, originally established in 1829 by William "Money" Williams, through a stock purchase. Chaires played a key role in founding the Union Bank of Tallahassee, a financial institution designed specifically for planters, as ownership of its shares was limited exclusively to plantation proprietors. Additionally, he co-established the Merchants and Planters Bank located in Magnolia.

In 1834, Benjamin and his brother Green were instrumental in organizing the Tallahassee Railroad, with Benjamin serving as one of its directors. His involvement extended to the Lake Wimico and St. Joseph Canal and Railroad Company, where he secured the contract for building a new rail line connecting St. Joseph to Iola on the Apalachicola River in early 1837. The financial turmoil caused by the Panic of 1837 put pressure on the company’s resources; when payment was offered in company-issued scrip, Chaires declined it, opting instead to accept monetary assets while overseeing a gradual continuation of construction. At the time of his death in 1838, he was serving as president of this railroad company.

Together with R. H. Berry, Chaires financed the General Samuel Parkhill, a vessel intended to ship cotton directly from ports on Apalachee Bay—namely Magnolia, Port Leon, and St. Marks—to Liverpool, thereby eliminating reliance on intermediaries in northern U.S. markets.

Wealth and Prominence

Chaires was widely regarded as Florida’s wealthiest individual during his time. The 1830 United States Census documented his ownership of 213 slaves, mostly young individuals, suggesting recent purchases. He has been referred to as "the territory’s first millionaire" and recognized as one of the most affluent and accomplished planters throughout Territorial Florida.

Within Tallahassee’s political scene, Chaires was affiliated with "The Nucleus," a faction aligned with Andrew Jackson that included prominent figures such as Governor Call, James Gadsden, Achille Murat, and John Bellamy. He was chosen as a delegate for Florida’s constitutional convention held between 1838 and 1839; however, he passed away before he could participate.

Death and Inheritance

Benjamin Chaires died in 1838 at the age of 52. In his will, he left to his wife Sarah the Verdura mansion along with 500 acres surrounding it, household furnishings, a carriage complete with driver, and one-tenth of his personal estate. His ten children were each bequeathed one-tenth of his estate except for daughter Mary Ann, who received $10,000 payable only after her husband’s death; her husband was explicitly excluded from benefiting from this inheritance. The executors named were his brother Green and son Joseph.

By 1839, Joseph Chaires had taken over management of the plantation; tax records from that year indicate ownership of 9,440 acres along with 80 slaves and carriages valued at $800. In 1842, foreclosure proceedings were initiated on estate property appraised at $35,570 (~$ in ). In 1845, the County Court distributed approximately 10,000 acres plus slaves, provisions, livestock, and equipment among the heirs.

By 1860, Joseph Chaires owned a plantation covering 3,800 acres in southeastern Leon County. The Bolton Plantation passed into the hands of daughter Martha; meanwhile, daughter Sarah Jane married George Taliafero Ward and integrated her land into Southwood Plantation.

Son Benjamin C. Chaires acquired smaller tracts of land and pursued a more conservative approach than many contemporaries. Unlike numerous planters who died burdened by debt, Benjamin Chaires’ descendants retained substantial landholdings without facing bank litigation.

Henry—the enslaved carriage driver left to Sarah Chaires—was interred in the family cemetery located near the ruins of the mansion.