Landscape forest management is an approach to meeting diverse objectives that collectively span multiple spatial scales. It is critical that we understand the long-term effects of landscape management on the structure and composition of forest tree communities to ensure that these practices are sustainable. Furthermore, it is increasingly important to also consider effects of our management within the context of anticipated environmental changes, especially future climate. This study investigated two decades of tree community dynamics within a long-term, landscape-scale management experiment located in a temperate deciduous forest in southeastern Missouri, USA. This experiment tests three alternative landscape management systems: even-aged management (EAM), uneven-aged management (UAM), and no-harvest management (NHM). Specifically, we evaluated effects of landscape management alternatives on: (1) structural and compositional dynamics of the tree communities and (2) adaptability of the tree communities to projected climate change. Changes in the abundance of dominant species under these landscape management systems suggested a prevailing successional trend on these relatively xeric, oak-dominated landscapes. In the overstory layer, there was a decrease in the abundance of red oak species (Section Lobatae), mainly black oak (Quercus velutina Lam.) and scarlet oak (Quercus coccinea Muenchh.), and an increase in white oak (Quercus alba L.) suggesting a shift to white oak dominance is underway. In the midstory and understory layers, flowering dogwood (Cornus florida L.) abundance declined substantially, while maples (Acer spp. L.) and several minor species increased. Declines in shortleaf pine populations indicated that regeneration harvesting is not regenerating this species. Experiment-wide changes in tree community composition suggest that adaptability to projected future climate may have increased over the first two decades of the MOFEP experiment under all management systems and that diverse management objectives can be realized through active management, including adaptation to climate change. However, future research is needed to test this working hypothesis and to more fully evaluate the impacts of silviculture treatments within the context of projected climate.