This study investigates the transformations promoted by digital technologies in contemporary political, social, and subjective dynamics, focusing on digital masses and cyberleadership. Based on the theoretical framework of Freudian psychoanalysis, the research analyzes how AI algorithms and other digital devices reconfigure social bonds and impact subjectivation processes. Through an interdisciplinary approach grounded in conceptual analysis, the study proposes to examine how Freudian metapsychology contributes to understanding the digital configurations of cyberculture, emphasizing the figure of the leader, a central element in the mass dynamics described by Freud. In effect, the aim is less to verify the validity of concepts and more to apply them to the particularities of the present moment. First, the theoretical foundations on masses are revisited in detail, to subsequently analyze the impact of digitalization, highlighting how algorithms and digital social networks shape subjectivities, intensify social divisions, and manipulate public opinions. These technological devices create informational bubbles and amplify mechanisms of control and alienation. Subsequently, the transformations in leadership in the digital era are addressed, focusing on cyber populism and the emergence of digital influencers as new forms of leadership. Bolsonarism is the case discussed to illustrate these dynamics. The research underscores how the control exercised by digital technologies favors discharges of the death drive, a central concept in Freudian theory, and intensifies the fragmentation of social bonds. It is argued that psychoanalysis, as an ethical and critical tool, can offer important contributions to analyzing digital phenomena and their impacts on subjectivity and social relations. The study concludes that in times of rapid technological transformations, it is necessary to preserve the singularity of the subject and rethink models of leadership and belonging in the digital context. Thus, the relevance of the interdisciplinary dialogue between psychoanalysis and technological studies is reaffirmed, indispensable for addressing the new forms of subjectivation, social control, and leadership emerging in the digital context.