While a sizeable gulf exists between the Trump and Biden administrations’ approaches to immigration, there is one policy area where these presidents would see eye-to-eye: a legal pathway for “Dreamers,” longtime undocumented residents who initially came to the U.S. as children. Notwithstanding this exceptional example of bipartisanship, how the nation now moves forward to create such a pathway is a conundrum. The political divide that has stalled a two-decades-long search for a congressional solution has its roots in America’s longstanding ambivalence about whether and how to provide basic opportunities to the least of its denizens. This Essay traces the current stalemate over the Dreamers to earlier disputes about desegregation and public school funding evident in a trio of landmark cases – Brown v. Board of Education, San Antonio Independent School District v. Rodriguez, and Plyler v. Doe – each of which highlights tensions underlying the Court’s commitments to ensuring equal protection of the law to minoritized communities. With respect to Dreamers in particular, the Obama/Biden approach will be compared to and contrasted with Trump’s policy perspective. Viewing these approaches from the lens of three constitutional themes – separation of powers, federalism, and individual rights – this Essay argues that true legislative progress for the Dreamers continues to be an uphill battle because of the history lessons gleaned from Brown through Plyler.