The 21st century re-emergence of so-called “strongmen” political leaders has once more brought into sharp relief important questions about the inter-relations between men, masculinity/ies and leadership. This chapter addresses these issues by highlighting the value of more critical perspectives. It argues that, when combined together, the insights of critical studies of men and masculinities (CSMM) and critical leadership studies (CLS) help to reveal how power in all its intersecting hierarchical and gendered forms can be exercised in and through men’s leadership discourses, decisions and practices. Parallel developments in both perspectives also point to the value of more critical dialectical approaches which suggest that while power may be enacted in oppressive, top-down ways, it is rarely all determining, monolithic and/or fixed. Although male-dominated leadership power dialectics are typically asymmetrical, they can also produce unintended, paradoxical and contradictory effects. This is illustrated by discussing some of the destructive, contradictory and self-defeating consequences that can emerge when men leaders’ decisions are informed by hypermasculine ways of thinking and acting.