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It has been argued that the recent financial crisis starting late 2007 is largely due to the opaqueness of structured bonds such as Mortgage-Backed Securities (MBS), Asset-Backed Securities (ABS), and Collateral Debt Obligations (CDOs). During the crisis, some insurance companies were also heavily involved and impacted. In this article, we analyze the opaqueness of structured bonds by examining U.S. insurers ’ assets from a capital markets perspective. We show that, before 2005, when structured products were less prevalent in the market, the market did not view structured bonds as opaque investments; however, after 2005, the market began to perceive the opaqueness in multi-class structured bonds, especially private bonds. In addition, by investigating the rating grade of such structured bonds, we find that the market views lower-grade private multi-class structured bonds as the most opaque, though graded public multi-class structured bonds are also considered opaque by the market, providing some foundations for the reform of credit rating agencies