We explain the use of legally unenforceable, discretionary financial contracts in circumstances where legally enforceable contracts are feasible. A discretionary contract allows a contracting party to choose whether or not to honor the contract. It is shown that such a contract liquefies reputational capital by permitting it to be depreciated in exchange for the preservation of financial capital and information reusability in financially impaired states. In addition, discretionary contracts foster the development of reputation. This explains discretion among highly confident letters, holding-company relationships, mutual-fund contracts, bank loan commitments, and other financial and nonfinancial contracts.