Isaac Jackson managed several estates in northern Jamaica during the years of transition from slavery to free labor. Based in Hanover Parish, County of Cornwall, Jackson oversaw the interests of as many as a dozen estates engaged in the production of sugar and other crops, rum, and cattle during the 1830s and 1840s. Jackson's letterbooks contain approximately 825 letters pertaining to the daily management of Jamaican plantations. Beginning just a year after the end of apprenticeship, the mostly formulaic letters addressed to absentee British landowners, their attorneys, ship captains, and other estate managers touch on sugar and rum production and crop yields and cattle husbandry, but more importantly, they map out the course of the hard-edged negotiations between landowners and laborers as they struggled to shape the new labor regime.