Silvopasture, the combination of trees, forage, and livestock, is a management practice that is gaining interest throughout the southeastern U.S. This research analyzed a hay-based alley cropping field trial that is transitioning into a silvopasture system. We planted four different tree spacings—2.4 × 2.4 m, 2.4 × 3.0 m, 3.0 × 3.0 m, and 1.8 × 3.0 m (8 × 8 ft, 8 × 10 ft, 10 × 10ft, and 6 × 10 ft)—of loblolly pine (Pinus taeda L.) and used secondary data for the possible planting of two different grass species—big bluestem (Andropogon gerardii Vitman) and switchgrass (Panicum virgatum L.). Tree inventories, forage samples, biometric modeling, and economic analysis of forage and timber monocultures and mixed systems were analyzed with discounted cash flow and capital budgeting analyses. Tree growth on the pasture site was exceptionally fast, generating high projected returns for timber monocultures, which exceeded returns for monoculture grass crops. Projected timber stand returns had the greatest Net Present Values (NPV) at the 4% discount rate, ranging between USD 3196 and USD 3552 per ha (USD 1294 and USD 1438 per ac) for a 2.4 × 3.0 m or 2.4 × 2.4 m tree spacing yield. Representative grass yields were obtained from secondary sources and had lower productivity, with switchgrass having the highest returns at USD 2581 per ha (USD 1045 per ac). Optimal NPVs for mixed silvopasture stands ranged between about USD 1500 per ha and USD 3500 per ha (USD 600/ac and USD 1400/ac), depending on the tree spacing within bands, the alley spacing, and the degree of competition between trees and grasses.