Callous Unemotional (CU) traits are associated with different environmental risk factors, such as negative stressful life events (SLE). The most common studied SLE associated with CU trait has been childhood maltreatment, but less is known about how other SLE impact the development of CU traits. Therefore, this work examines risk factors, personal factors (executive functioning), and mental health outcomes associated with the trajectories of Callous Unemotional (CU) traits and Stressful Life Events (SLE) in a community sample of children. A cohort of 377 preschoolers were followed up between ages 3 and 10. Several risk factors and outcomes for three trajectory groups (high CU/SLE; high CU/low SLE; and the reference group with low CU/SLE) were analyzed by using multiple post-hoc comparisons. We hypothesized that children with high CU/SLE would face more contextual risk factors, more executive functioning difficulties and more mental health problems than children with high CU/low SLE or the reference group. At the age of 3, children who showed high CU/SLE faced more early contextual adversity, including socioeconomic difficulties and maternal antisocial behavior than the other groups of children. At the age of 10, children with high CU/SLE presented more peer problems and higher psychopathology symptoms than the reference group, but no differences on mental health outcomes in comparison to the high CU/low SLE group. These results have potential implications for clinical practice and studies attempting to identify different CU subtypes in children.