This paper exploits the features of trust preferred stock to examine several tax and financial reporting issues. Trust preferred stock, first issued in 1993, was engineered to be treated as preferred stock for financial statement purposes and as debt for tax purposes (i.e., payments on trust preferred stock are deductible by the issuer).' Our analyses are intended to shed new light on three issues: (i) the extent to which firms will incur costs to manage the balance sheet classification of a security; (ii) the magnitude of net tax benefits, if any, associated with leverage-increasing