How did political institutions emerge and evolve under colonial rule? This article studies a key colonial actor and establishes core democratic contradictions in European settler colonies. Although European settlers’ strong organizational position enabled them to demand representative political institutions, the first hypothesis qualifies their impulse for electoral representation by positing the importance of a metropole with a representative tradition. Analyzing new data on colonial legislatures in 144 colonies between the seventeenth and twentieth 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 in colonies that established early representative institutions. Applying class-based democratization theories predicts perverse institutional evolution—resisted enfranchisement and contestation backsliding—because sizable European settler minorities usually composed an entrenched landed class. Evidence on voting restrictions and on legislature disbandment from Africa, the British Caribbean, and the US South supports these implications and rejects the Dahlian path from competitive oligarchy to full democracy.