We provide evidence that Chief Executive Officers (CEOs) with relatively high inside debt holdings are more likely to engage in asset sell-offs. This finding remains strong even after employing various methodologies to mitigate endogeneity concerns. Further examination reveals that the positive impact of inside debt on sell-off likelihood is primarily evident for deals that reduce firm risk, suggesting that the CEO's inside debt holdings incentivize them to favor risk-averse strategies when restructuring the firm. The relation holds regardless of pre-sell-off firm performance, governance quality, or the CEO's power or proximity to retirement, underscoring that the desire to reduce risk is the primary channel through which inside debt incentivizes sell-offs. Post-sell-off, firms show signs of better realignment with debt holders' interests including reductions in financial leverage and improvements in interest coverage ratios.