Patterns in the dominance of evergreen vs. deciduous plants have long interested ecologists, biogeographers, and global modellers. But previous models to account for these patterns have significant weaknesses. Bottom-up, mechanistic models – based on physiology, competition, and natural selection – have often been non-quantitative or restricted to a small range of habitats, and almost all have ignored belowground costs and whole-plant integration. Top-down, ecosystem-based models have succeeded in quantitatively reproducing several patterns, but rely partly on empirically derived constants and thresholds that lack a mechanistic explanation. It is generally recognized that seasonal drought can favor deciduous leaves, and that infertile soils can favor long-lived evergreen leaves. But no model has yet explained three great paradoxes, involving dominance by 1) evergreens in highly seasonal, boreal forests, 2) deciduous larch in many nutrient-poor peatlands, and 3) evergreen leaf-exchangers in nutrient-poor subtropical forests, even though they shed their leaves just as frequently as deciduous species. This paper outlines a generalized optimality model to account for these and other patterns in leaf longevity and phenology, based on maximizing whole-plant carbon gain or height growth, and building on recent advances in our understanding of the quantitative relationships of leaf photosynthesis, nitrogen content, and mass per unit area to leaf life-span. Only a whole-plant approach can explain evergreen dominance under realistic ecological conditions, or account for the boreal paradox, the larch paradox, the leaf-exchanger paradox, and expected shifts in shade tolerance associated with leaf phenology. Poor soils favor evergreens not merely by increasing the costs of nutrient acquisition, but also by depressing the maximum rate of photosynthesis and thus the seasonal contrast in photosynthetic return between leaves adapted to favorable vs. unfavorable conditions. The dominance of evergreens in western North America beyond the coastal zone of mild winters and winter rainfall appears related to the unusually long photosynthetic season for evergreen vs. deciduous plants there. Future models for optimal leaf phenology must incorporate differences between evergreen and deciduous plants in allocation to photosynthetic vs. non-photosynthetic tissue, rooting depth, stem allometry, xylem anatomy, and exposure to herbivores and leaching, and analyze how these differences interact with the photosynthetic rate, transpiration, and nutrient demands of leaves with different life-spans to affect rates of height growth in specific microsites.