In this paper, we incorporate a positive theory of unemployment insuranceinto a dynamic overlapping generations model with search-matching frictionsand on-the-job learning-by-doing. The model shows that societies populatedby identical rational agents, but differing in the initial distributionof human capital across agents, may choose very different unemploymentinsurance levels in a politico-economic equilibrium. The interactionbetween the political decision about the level of the unemployment insuranceand the optimal search behavior of the unemployed gives rise to aself-reinforcing mechanism whichmay generate multiple steady-stateequilibria. In particular, a European-type steady-state with highunemployment, low employment turnover and high insurance can co-exist withan American-type steady-state with low unemployment, high employment turnoverand low unemployment insurance. A calibrated version of the model featurestwo distinct steady-state equilibria with unemployment levels and durationrates resembling those of the U.S. and Europe, respectively.