How did political institutions emerge and evolve under colonial rule? Although European settlers’ strong organizational position enabled demanding representative political institutions, this article establishes core democratic contradictions in European settler oligarchies. The first hypothesis qualifies Europeans’ impulse for representative institutions by positing the importance of a metropole with a representative tradition. Analyzing new data on colonial legislatures in 144 colonies between the 17th and 20th centuries shows that only British settler colonies—emanating from a metropole with representative institutions—systematically exhibited early elected legislative representation. The second hypothesis highlights a core democratic contradiction even in colonies that established early representative institutions. Extending class-based democratization theories predicts perverse institutional evolution—resisted enfranchisement and contestation backsliding—because sizable European settler minorities usually composed an entrenched landed class, rejecting the heralded Dahlian path from competitive oligarchy to full democracy. Evidence on voting restrictions and on legislature disbandment from Africa, the British Caribbean, and the U.S. South supports these implications