Insurance companies have large holdings of financial securities that generate returns that are taxed at both the corporate and personal levels in the U.S. If the same securities were held by a pass-through entity such as a mutual or hedge fund, the returns would be taxed only at the personal level, which implies a corporate tax disadvantage of holding assets in an insurer. There is, however, a personal tax advantage of holding some securities with an insurer. This paper examines the implications of personal taxes for an insurer’s tax cost on equity capital and how the tax costs have varied over time under different tax regimes and how they vary with different asset portfolios. The paper also discusses offshore hedge fund reinsurers, which provide an interesting case study illustrating the relevance of personal taxes.