Romania ranks at the extreme low end in Eastern Europe in terms of Hofstede cultural insights, rule of law, government effectiveness, and corruptionpotentially limiting governance quality for restricting resource channeling. In this paper, we examine whether these shortcomings flow over into the degree of corporate insider trading profitability at the firm level. Consistent with high power distance, low individualism, and voice and accountability, executives and their family members extract higher returns. The conjectured monitoring constraint of equity ownership had little impact on reducing profitable trading. Second, media reporting of firm-related scandals only restrained insider profitability in firms with government ownership-consistent with general forbearance of corruption and sanction from the use of politically controlled assets. Third, the global financial crisis revealed both a crisis of inept trading consistent with high uncertainty avoidance and also highly profitable trades for a limited set of executives who undertook short-term reversal strategies. Our exploratory microanalysis suggests a prototype to highlight areas