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The United States Supreme Court's recent decision in Board of Trustees of the University of Alabama v. Garrett further circumscribed Congress' power to enforce the Fourteenth Amendment. The Court's recent decisions in this area insist that enforcement legislation be congruent and proportional to the constitutional violations sought to be remedied. The specter of reduced leeway for congressional enforcement authority requires Congress to approach such federal legislation carefully. The Employment Non-Discrimination Act (ENDA), proposed legislation prohibiting sexual orientation discrimination in employment, provides an interesting case study of the Court's recent Section 5 jurisprudence. This Article, after outlining historic and current Section 5 standards, uses Garrett as a guide to examine whether the Supreme Court would uphold ENDA's provision allowing state employees to sue their employers for certain types of retrospective relief. The Article both argues that ENDA is a valid expression of Congress' Section 5 power and provides strategies for navigating the increasingly narrow confines of Fourteenth Amendment enforcement power to provide critical employment protections.