In recent years, gangsterism and gang related activities among Indians are perplexing and alarming. Although this issue is considered as an old phenomenon, researches related to underlying factors for gangsterism are still lacking. With this in mind, this study aimed to explore psychological and criminogenic factors behind gangsterism among Indians in Malaysia. This study utilized a non-experimental research design. This study is a qualitative research (semi-structured, face-to-face individual interview guide) that makes use of the inductive approach based on a combination of subjectivism and interpretivist philosophies. Six ex-gangsters and four police personnel were interviewed; and their experiences of gangsterism were used to gain a reality-based understanding regarding the factors underlying gangsterism. The thematic analyses generated three psychological factors (negative emotional responses, low self-control, and high impulsivity) and three criminogenic factors (substance abuse, having antisocial peers, and dysfunctional families). One new theme emerged: monetary gain, with three sub-themes (ease of obtaining money, amount and immediacy, and benefits derived from illegal monetary gains). The outcome of this explorative research provides insight to the growing body of knowledge on gangsterism in Malaysia and is useful for community leaders and law enforcement agencies to strategize appropriate intervention, prevention, and suppression efforts to combat gangsterism.