Although neither the Congress nor the courts have articulated a clear standard by which substantial asset sales should be judged, this Note argues that the case law of the Lionel canon has been far from inconsistent. In fact, the Lionel canon reflects a profound skepticism of substantial asset sales and an attempt to address apparent inequities in particular sales, rather than a rule of perfunctory approval where a minimum business justification threshold has been met. In Part II, this Note describes the origin of the business justification rule and the courts’ early skepticism of a mere business justification standard. In Part III, this Note reexamines the Lionel canon and determines three themes that pervade the skepticism attending to substantial asset sales: the need for sale term neutrality, a distrust of asset pricing, and a concern for distributional fairness. With a more comprehensive understanding of these themes and their effects on the reorganization process, Part IV presents a new framework — grounded in the Lionel canon — by which substantial asset sales may be judged. Under the framework, sales that predetermine the outcome of creditor negotiations or involve bad faith, self-dealing, fraud, or a flawed sales process should be rejected; the remaining sales should be approved only if the asset value is decreasing or if the debtor sustains the burden of showing a benefit to the estate. Finally, Part V applies the proposed framework to the bankruptcies of Lehman, Chrysler, and General Motors. This Note concludes that the Lehman court was justified in approving the sale of Lehman’s assets because the sale did not predetermine the outcome of creditor negotiations or involve bad faith or a flawed sales process, and because Lehman’s assets were rapidly declining in value. Conversely, Chrysler and GM included flawed sales processes that arguably delivered less than full and fair value to the estate; accordingly, the Chrysler and GM courts should have rejected the sales.