This study addresses a gap in the current corporate crime literature by giving special attention to the characteristics and role of the top management team (TMT) in facilitating or mitigating illegal conduct. I ask how changes in certain demographic characteristics of the TMT unit, particularly gender composition, affect various forms of corporate offending over time. Specifically, 1) In what ways are changes in TMT gender characteristics related to corporate illegality over time? 2) What is the nature of the relationship between TMT gender diversity, corporate offending, and other key characteristics of women executives? 3) What is the temporal order of these relationships? 4) How do other TMT and corporate characteristics influence the relationships between TMT gender diversity and firm offending? Stemming from the strategic leadership literature, Hambrick and Mason’s (1984) Upper Echelons (UE) perspective serves as the primary theoretical framework guiding this study. This dissertation focuses on two types of corporate illegality: environmental and financial (i.e., accounting fraud, bribery, and anticompetitive acts) using a universe of firms listed on the S&P 1500 from 1996 through 2013.