Prior studies show that stressful life events are associated with greater magnitude of incapability and symptom intensity. We sought to understand the association of such events (i.e., both adverse childhood experiences and recent difficult life events [DLEs]) alongside feelings of worry or despair and unhelpful, on the magnitude of incapability and symptom intensity in musculoskeletal patients. One hundred and thirty-six patients presenting for musculoskeletal specialty care completed measures of incapability, pain intensity, adverse childhood experiences, DLEs in the last year, unhelpful thoughts, symptoms of anxiety and depression, and sociodemographic factors. Factors associated with the magnitude of incapability and pain intensity were sought in multivariable analysis. Accounting for potential confounders, greater incapability was associated with greater unhelpful thoughts (RC = −0.81; 95% CI = −1.2 to −0.42; P ≤ .001), but not with stressful life events (either during childhood or more recently). Greater pain intensity was associated with greater unhelpful thoughts(RC = 0.25; 95% CI = 0.16 to 0.35; P ≤ .001) and being divorced or widowed (RC = 1.8; 96% CI = 0.43 to 3.2; P = .011), but again, not with stressful life events. The strong association of unhelpful thoughts with magnitude of incapability and pain intensity can motivate musculoskeletal specialists to anticipate patients expressing negative pain thoughts and behaviors. Future studies might account for social and environmental context behind stressful life events and the influence of resiliency and pain-coping strategies on these interactions. Level of Evidence: Level III, prognostic study