The structure and developmental dynamics of old-growth forests often serve as important baselines for restoration prescriptions aimed at promoting more complex structural conditions in managed forest landscapes. Nonetheless, long-term information on natural patterns of development is rare for many commercially important and ecologically widespread forest types. Moreover, the effectiveness of approaches recommended for restoring old-growth structural conditions to managed forests, such as the application of extended rotation forestry, has been little studied. This study uses several long-term datasets from old growth, extended rotation, and unmanaged second growth Pinus resinosa (red pine) forests in northern Minnesota, USA, to quantify the range of variation in structural conditions for this forest type and to evaluate the effectiveness of extended rotation forestry at promoting the development of late-successional structural conditions. Long-term tree population data from permanent plots for one of the old-growth stands and the extended rotation stands (87 and 61 years, respectively) also allowed for an examination of the long-term structural dynamics of these systems. Old-growth forests were more structurally complex than unmanaged second-growth and extended rotation red pine stands, due in large part to the significantly higher volumes of coarse woody debris (70.7 vs. 11.5 and 4.7 m3/ha, respectively) and higher snag basal area (6.9 vs. 2.9 and 0.5 m2/ha, respectively). In addition, old-growth forests, although red pine-dominated, contained a greater abundance of other species, including Pinus strobus, Abies balsamea, and Picea glauca relative to the other stand types examined. These differences between stand types largely reflect historic gap-scale disturbances within the old-growth systems and their corresponding structural and compositional legacies. Nonetheless, extended rotation thinning treatments, by accelerating advancement to larger tree diameter classes, generated diameter distributions more closely approximating those found in old growth within a shorter time frame than depicted in long-term examinations of old-growth structural development. These results suggest that extended rotation treatments may accelerate the development of old-growth structural characteristics, provided that coarse woody debris and snags are deliberately retained and created on site. These and other developmental characteristics of old-growth systems can inform forest management when objectives include the restoration of structural conditions found in late-successional forests.