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In this short commentary, we explore the use of two interrelated pedagogical methods for teaching transactional and business law. The first method is deal deconstruction, which analyzes the set of final deal documents and outcomes. This method is backward-looking, conducting a post-mortem on business transactions and analyzing the parties’ choices memorialized in the agreement against the legal and financial alternatives. The second method involves case studies and simulations, which are commonly seen in business schools. This method is forward-looking, exposing students to the uncertainties and situational contexts of doing deals and deal-related litigation. Together, these complementary methods help students understand the tradeoffs and dynamics of transactions and deal negotiations. They provide pedagogical alternatives to the traditional Langdellian method, which relies heavily on the study of edited appellate opinions. By presenting problems in different packages and from different temporal perspectives, these methods hone analytical, deal structuring, problem-solving, and decision-making skills.