David Gamage (Missouri) presents Confronting The Tax-And-Oligarchy Catch-22 at Toronto, as part of its James Hausman Tax Law and Policy Workshop Series hosted by Ben Alarie:

Why have taxes on concentrated wealth weakened across decades, even though polling typically shows strong majority support? This Article argues that the answer lies in a structural dynamic we call the tax-and-oligarchy catch-22. Taxing extreme wealth is among democracy’s most direct tools for constraining oligarchic power, yet extreme wealth reliably finances the political work of blocking, diluting, or unwinding such taxes. The catch-22 operates through political optionality. When the wealthiest households can defer tax indefinitely, they preserve capacity for campaigns, litigation, lobbying, and producing expert doubt about reforms that might reach them. Every dollar of deferred tax is a dollar available to lobby against its own eventual collection. Progressive Era reforms were designed to interrupt this dynamic. For decades they partially succeeded. But the constraints have eroded, and today’s largest fortunes face minimal effective taxation.

This Article responds with a democratic tax firewall, an approach that treats durability as a first-order design constraint rather than an afterthought. Drawing on political science, history, and recent state-level campaigns, we identify design choices that can help reforms resist quiet erosion and show how sustained technical preparation can position reformers to act when political windows open.