Conflicting Values in Judicial Valuations

Do courts employ finance neutrally and consistently, or do different courts fashion financial tools in court-specific ways? I assemble 20 years (52,000 pages) of judicial opinions, legal briefs, and expert reports from three settings where statutes assign courts an ostensibly shared job of valuing business interests: Delaware Chancery shareholder appraisals, Tax Court estate & gift tax cases, and Bankruptcy cramdowns. With natural language processing, a large language model, and hand-performed review, I show that valuation practice is organized into court-specific epistemic ecosystems: courts rely on largely non-overlapping bodies of financial scholarship, valuation case law, and economic expert witnesses. These silos correspond to systematic differences in valuation reasoning and outcomes across courts. Chancery methodological idiosyncrasies, meticulously explained, systematically produce relatively high valuations of private and weakly traded business interests, while Tax Court idiosyncrasies produce relatively low ones. The same minority interest in a typical private firm is worth roughly twice as much for appraisal purposes as for gift tax purposes. Bankruptcy Court valuation reasoning, by contrast, is too vague to be systematically reconstructed. Does each court's valuation practice align with theoretical accounts of each underlying law's distinctive purpose? Bankruptcy opacity reflects institutional pressures for speed and flexibility in reorganizations. Delaware's detailed jurisprudence mirrors corporate law's orientation towards aiding transactional planning, while its substantive outcomes reflect concern over minority shareholder protection. Tax Court valuation practices appear to sit in tension with leading accounts of the estate & gift taxes. The contrast between Delaware's "fair value" standard and the Treasury's "willing buyer, willing seller" formulation helps illuminate the institutional challenges of transfer tax valuation.