This paper explores why Jordan Belfort, despite being a criminal, abuser, and drug addict, continues to inspire admiration among some men and attraction among some women. Drawing on film analysis, psychology, and neuroscience, it argues that Martin Scorsese’s The Wolf of Wall Street operates not only as a cautionary tale but also as a vehicle of glorification. It also constructs a psychological profile of Belfort, emphasizing traits consistent with personality disorders, particularly narcissistic, antisocial, and borderline patterns. Simultaneously, it examines the psychological mechanisms behind male aspiration toward figures like Belfort and the trauma bonds that kept his former wife entrapped, extending this analysis to the broader profiles of women drawn to men with power, wealth, and status. Finally, it situates Belfort’s psychological makeup alongside case comparisons to other financial criminals and charismatic leaders, and expands on the neuroscientific underpinnings of his manipulative charisma and followers’ susceptibility.