This cultural history examines slave trading in Kentucky from 1820 to 1860. I argue that instead of slavery declining in Kentucky during the antebellum period, the state’s system of intrastate slave speculation, which included the practices of slave hiring and slave catching, provided Bluegrass masters with a profitable and flexible system of circulating enslaved black labor throughout communities and within the state. Slavery in Kentucky existed in a diverse agricultural economy, not a cotton producing economy as in the Lower South and this type of slavery characterized by masters who possessed five or fewer slaves shaped the practice of slave speculation in Kentucky. White Kentuckians were involved in the slave market not just as professional flesh traders but also as hirers, auctioneers, executors, sheriffs, and slave catchers. This study of slave speculation in Kentucky expands our existing definition of slave trading in the antebellum South to include the practices of slave hiring and slave catching and also reveals how the speculation in human beings affected the potency of antislavery movements in the Upper South.