The possible differential response to the climatic fluctuations of co-occurring trees of different ages is still poorly known and rather controversial. Moreover, in managed forests, such a picture is further complicated by the impact of silvicultural practices. With this concern, in a multi-aged umbrella pine stand in the Maremma Regional Park (Tuscany, Italy), the spatial patterns and tree-ring response to the climate were investigated by differentiating trees into three classes, i.e., young, mature, and old. The aim was to assess the role of past management in shaping the current stand structure and affecting the growth dynamics at different ages, as well as to evaluate the possible shifting of tree adaptation to the climatic variables throughout plant aging. Our outcomes proved that the current mosaic of even-aged small patches results from a multifaceted forest management history. Until the 1960s, silvicultural treatments seemed more suitable in promoting tree growth and regeneration. Later on, inappropriate and/or untimely thinning probably triggered excessive competition from the top canopy trees, involving reduced stem and root system development in the younger plants living in the understory. Also, the intra-annual growth response to the climate showed some dependence on age. Younger trees are assumed not to be able to efficiently exploit water resources from the deep aquifer during the dry season, probably due to an insufficiently developed taproot, differently than older trees. Accordingly, appropriate and timely thinning, simulating frequent natural disturbances on small areas, could be a suitable management approach to promote sustained growth rates and regeneration processes, as well as healthy and vital trees at all life stages.