In this brief introduction, we highlight the critical contributions of the esteemed scholar, historical sociologist and theoretical historian, Dale Tomich, whose scholarly interventions have contributed to changing the field of plantation slavery, studies of capital and historical studies in general. We emphasize his key historical and methodological interventions, particularly the importance of studying locales at several intersecting scales, underscoring the world economy as ultimately the main unit of analysis as it operates differentially across the Atlantic and beyond. Moving among these interconnected and relational scales we argue has allowed for a more complex understanding of how even ‘small islands’ like those in the Caribbean facilitate ‘huge comparisons,’ influence and are shaped by deterritorialized forces emanating from the world economy. Tomich’s work we argue, theorizes and historizes from the top to the bottom and vice versa, a necessary labor for apprehending how subject-citizens navigate their worlds in their various locales.