This article reconstructs and explains variability in pathways of smallholder cacao expansion and land use and cover change (LUCC) over the past four decades in Southeast Sulawesi, Indonesia. I first draw on approaches from remote sensing (RS) to reconstruct cacao expansion in two top-producing districts (1972–2014), highlighting the variegated environment changes shaped by smallholder cacao plantings, both inside and outside forested lands. I then integrate these data with theories and methods from political ecology (PE) and critical physical geography (CPG) to document the uneven politics of land and capital access mediating this variability. Using these data, I argue that variability in crop expansion and LUCC should not be considered as an exception but as the norm; integral to any generalizable explanation of LUCC. I also show how a focus on variability can not only supplement but also shift dominant accounts of LUCC.