Thomas S. Drew was born in August 1802 in Wilson County, Tennessee, the son of a gunsmith. His family later moved to Louisiana. In 1817 Drew moved to Clark County in the Arkansas Territory, where he worked as a peddler and as a schoolteacher. In 1824 he became clerk for the Clark County Court and justice of the peace for Caddo Township. The following year he became postmaster with a contract to carry mail in Clark County.
In 1827 Drew married Cinderella Bettis, the daughter of a prosperous Missouri landowner. As a wedding present the couple received 800 acres in northeast Arkansas near the present-day town of Biggers. By 1832 Drew had established himself as a prominent planter and a power in local politics. That same year he was elected judge of the Lawrence County Court.
In 1835 Drew's plantation became part of the newly created Randolph County. He was chosen as the county's delegate to the statehood constitutional convention, where he helped resolve the conflict over how slaves were to be factored in determining representation.
From 1836 to 1844, Drew became an influential figure within the Democratic Party, playing the role of a mediator between the various factions. When Yell liquidated the State Bank, for example, Drew was chosen as financial receiver for its Batesville branch.
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