Hypermobility of the trapeziometacarpal joint is commonly considered to be a potential risk factor for osteoarthritis. Nevertheless, the results remain controversial due to a lack of quantitative validation. The objective of this study was to evaluate the effect of joint laxity on the mechanical loadings of cartilage. A patient-specific finite element model of trapeziometacarpal joint passive stiffness was developed. The joint passive stiffness was modeled by creating linear springs all around the joint. The linear spring stiffness was determined by using an optimization process to fit force–displacement data measured during laxity tests performed on eight healthy volunteers. The estimated passive stiffness parameters were then included in a full thumb finite element simulation of a pinch grip task driven by muscle forces to evaluate the effect on trapeziometacarpal loading. The correlation between stiffness and the loading of cartilage in terms of joint contact pressure and maximum shear strain was analyzed. A significant negative correlation was found between the trapeziometacarpal joint passive stiffness and the contact pressure on trapezium cartilage during the simulated pinch grip task. These results therefore suggest that the hypermobility of the trapeziometacarpal joint could affect the contact pressure on trapezium cartilage and support the existence of an increased risk associated with hypermobility.