The lack of economic information for management of longleaf pine, a forest type that once dominated the landscape in the southeastern United States, can be a major barrier to landowners to planting this species. This study compares the economic performance of even-aged longleaf pine with loblolly pine. We assume that a longleaf pine stand produces timber, water yield, wildlife habitats and pinestraw raking, while a loblolly pine stand is managed exclusively for timber production. For both species, future timber prices are uncertain and harvest decisions will be made following an optimal adaptive harvest strategy. Our findings show that investing in longleaf pine plantations is not generally an economically attractive option compared to loblolly pine for landowners. On average, the land expectation value for loblolly pine is $4610 ha −1 higher than the land expectation value of longleaf pine. Stronger markets for water yield ($0.04-$0.073 k-liter −1) can favor the competitiveness of longleaf over loblolly pine. In the absence of increased payments for water production, landowners require financial incentives between $235-$642 ha −1 over 15 years, to switch from planting loblolly to longleaf pine. When water payments are included ($0.03-$0.0 k-liter −1), incentives between $173-320 ha −1 are required to plant longleaf instead of loblolly pine.