Contemporary capitalist societies use different institutions to manage economic risks. While different public welfare state and financial institutions (banks, capital markets) have been studied across coordinated and liberal market economies, the different worlds of private insurance institutions have been understudied. Building on new insurance data sets (1880–2017), we find that countries with a Maritime (USA, GBR, CAN) in contrast to the more backward Alpine (AUT, DEU, CHE) insurance tradition developed bigger life and nonlife insurance earlier, with less state-associated and reinsurance enterprises, but riskier investments steered toward financial markets. We argue that the larger and more “Maritime” the insurance sector, the more it made welfare states liberal and securities markets large. Insurance is thus a hidden factor for countries’ varieties of capitalism and worlds of welfare. The recent convergence on the Maritime model, however, implies that the riskier and risk-individualizing type of private insurance has added to privatization and securitization trends everywhere.