This paper explores the conference themes through focusing on the often arbitrary and contingent forces which operate to separate ‘success’ and ‘failure’ in business, and thereby determine its ‘winners’ and ‘losers’. Drawing on current insistence at highest policy level that competitiveness and pre-eminence in business must not to be achieved at the expense of propriety, and on nineteenth-century events, the paper points to how allocations of status of ‘winning’ and ‘losing’ within capitalist systems do not necessarily follow from exercising propriety and probity or even soundness in the conducting of business affairs. It is suggested key operational forces acquire especial significance where public consequences can attach to alleged misconduct in business. The paper examines these issues principally through the lens of criminal liability which - in being widely regarded as embodying the State’s right to castigate and punish socially injurious behaviour - can in many ways be regarded as the ultimate consequence of being a ‘loser’ rather than ‘winner’ in business. The paper also considers how criminal liability might be the ultimate statement in inequality in business spheres, exploring how criminal enforcement might be regarded as an instrument of marginalization, unfairly penalizing ‘outsiders’ and reinforcing dominant practices and favouring established networks.