Restoration of composition, structure, and function in oak dominated ecosystems is the focus of management in temperate forests around the world. Land managers focused on oak ecosystem restoration are challenged by the legacy effects of complex land-use histories, urbanization, climate change, and potential stakeholder response to management. Trade-offs may exist between managing forests for climate mitigation (e.g., maximizing C storage or sequestration) and promoting shade-intolerant species historically associated with frequent or high-severity disturbances. This study assessed the potentially conflicting goals of sustained live biomass accrual and increased oak regeneration in the East Woods Natural Area at The Morton Arboretum in Lisle, IL, USA. We evaluated how biomass trends and oak regeneration were related to management regimes, land-use history, current stand structure and composition, and topoedaphic factors. Our results indicated no significant trade-off between sustained live biomass accrual and oak regeneration. Live biomass was increasing across the landscape (biomass increment averaged 18,186 kg ha^-1 yr^-1) and was not strongly related to differences in management or land-use history. Oak regeneration was rare, especially beyond the seedling stage (~226 seedlings and 9 saplings ha^-11) and was also not strongly related to recent management. Our results indicate that even 20+ years of annual prescribed burning combined with understory thinning has failed to produce the open canopy conditions and high light availability that are necessary for successful oak recruitment. The absence of any trade-offs between biomass accrual and oak regeneration may, therefore, be largely related to the ineffectiveness of current management for promoting oak regeneration. More intensive management utilizing canopy manipulations could produce greater trade-offs, but is likely necessary to establish and release oak regeneration.