In this study, triangular specimens of southern pine (Pinus spp.; SP) generated by a star-sawn process were characterized according to knots and deformation. SP specimens were used to understand the differences among glue-line combinations of radial-to-radial, radial-to-tangential, and tangential-to-tangential faces bonded with phenol resorcinol formaldehyde resin. The specimens were tested for shear strength, dimensional stability, wood failure, and delamination rate in accordance with ASTM D1037 and D2559 standards. Among the star-sawn triangular samples studied, bows in tangential-face sections occurred the most. The radial-face sections of SP triangular specimens had more knots but a much lesser degree of deformation than the tangential-face sections. The tangential-to-tangential face glue-line samples showed a lower shear strength, more wood failure, and a greater tendency of delamination and dimensional change, especially when subjected to wet conditions. Confocal microscopic pictures revealed that the tangential-to-tangential glue line showed a greater tendency of deformation in the earlywood part and helped to explain the reason for poor glue-line durability and low shear strength. This article revealed that the star-sawn–process generated wood radial-face samples were more stable than others tested and are perhaps a good alternative for massive panel manufacturing.