A discrete element model is proposed to examine rock strength and failure. The model is implemented by UDEC, which is developed for this purpose. The material is represented as a collection of irregular-sized deformable particles interacting at their cohesive boundaries. The interface between two adjacent particles is viewed as a flexible contact whose constitutive law controls the material fracture and fragmentation properties. To reproduce rock anisotropy, an orthotropic cohesive law is developed for the contacts, which allows their shear and tensile behaviors to be different from each other. Using a combination of original closed-form expressions and statistical calibrations, a unique set of the contact microparameters are found based on the uniaxial/triaxial compression and Brazilian tension test data of a plaster. Applying the obtained microparameters, joint specimens, made of the same plaster, are simulated, where the comparison of the obtained results to laboratory data shows a reasonable agreement.