The metaphor of the casino, with its associations of risk, uncertainty and illusion resonate at different levels of the contemporary cultural and political imagination where notions of chance and luck – together with the arbitrariness of being either a ‘winner’ or a ‘loser’ are pervading themes. This talk draws on object relations psychoanalysis to discuss the notion of casino culture as a psycho-cultural formation and its relationship to the emergence of what I call ‘casino politics’, within the current era of risky populist politics within the US and the UK. The talk combines cultural and political analyses with the psychoanalytic theories of Donald Winnicott (1971), Christopher Bollas (1987) and Thomas Ogden (1992) who in different ways foreground the role of play, illusion and the fantasy of transformation in their work. Such an approach is useful because of its focus on the seemingly irrational affective, unconscious investments that underpin the ideology of casino culture and its politics – particularly in the context of Brexit politics in the UK and Trump’s presidency in US, where fantasies associated with gambling are often mobilized to gain mastery over uncertainty and loss.