Men are overrepresented at the highest levels of leadership in nearly every industry, despite studies that report that men are seen as having less effective leadership abilities than women (Bureau of Labor Statistics, 2017a; Bureau of Labor Statistics, 2017b; Catalyst, 2018a; Catalyst, 2019a; Catalyst, 2019b; Taylor et al., 2008; U.S. Department of Education, 2016a; Warner, 2014). This leadership phenomenon is also seen on U.S. college campuses where college men attain leadership positions yet are underrepresented in educationally-purposeful activities such as leadership training (Burns et al., 2008; Dugan et al., 2008; Higher Education Research Institute [HERI], 1996; Lester & Harris, 2014; National Survey of Student Engagement, 2019; Salgado, 2003; Salisbury et al., 2010; Sax, 2008; Wilson, 2000). In order to examine this divide, this study utilized an embedded case study that compared the experiences and perceptions of 35 college men from two different cohorts - men who engaged in leadership training while in college and men who did not engage in leadership training - in order to understand the influence that gender has on college men's propensity to participate in leadership training. In depth interviews were conducted and photo elicitation was employed and the resulting data were examined using a conceptual framework derived from literature related to gender production, reproduction and reinforcement to answer three research questions: 1) In what ways, if any, does gender production, reproduction and reinforcement inform college men's perceptions on leadership?; 2) In what ways, if any, does gender production, reproduction and reinforcement inform college men's perceptions of their own leadership self-efficacy? and 3) Why do some college men engage in leadership training while others do not? These questions generated data that showed little dissonance between the cohorts related to their gender identity and leadership development, suggesting that gender production, reproduction and reinforcement has a significant effect on college men's leadership and gender identity. Both cohorts attributed their masculine identity development to their fathers and father-like figures, who provided participants with meaningful messages about leadership. Additionally, both cohorts credited their involvement in sports programs as a pivotal factor in their gender and leadership development. Key differences between the cohorts included their views on positional authority as well as how the two groups conceptualized the concept of leadership, specifically the ways in which the non-leadership cohort articulated their leadership abilities in a more boastful, arrogant and absolute manner compared to the more humble, reserved and nuanced approach of the leadership cohort. Overall, the findings from this study suggest that gender production, reproduction and reinforcement have a significant effect on college men's leadership and gender identity as well as on their propensity to engage in leadership training due to societal influences that provide men with messages that they are already effective leaders, regardless of their actual leadership acumen. As such, this study offers recommendations for policy improvements and practice interventions that would engage college men in leadership training while also allowing for critical reflection and examination of masculinity. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]