This study investigates whether controlling shareholders with managerial entrenchment, as measured by greater deviation in cash flow and control rights, are associated with managerial liability coverage. Using a sample of director and officer (D&O) liability insurance data, we find that firms with more serious agency conflicts between controlling and outside shareholders are more likely to purchase D&O liability insurance. We also find that controlling shareholders who face greater litigation risk have an incentive to carry abnormally high D&O liability insurance coverage. Our results indicate that an incentive exists to acquire managerial liability coverage against litigation risks arising from incentive conflicts between controlling and outside shareholders.