In the transition from military rule to democracy, the government of Augusto Pinochet bequeathed to Chile a unique electoral law by which all legislative seats are contested in two-member districts. A key implication of this rule is that in order to secure legislative majorities, coalitions have to put their strongest candidates in the most precarious electoral list positions. This generates a divergence of interests between coalitions and politicians. Chile's largest coalition, the Concertación, has resolved the dilemma by providing appointed posts to unsuccessful congressional candidates who accept personal political risk on the coalition's behalf. This study argues that this insurance system has provided the critical glue to hold the coalition together since Chile's transition to democracy in 1990. Recent changes in the electoral environment could threaten the Concertación's control over the appointed posts that have sustained this informal institution. This could jeopardize the Concertación's cohesion during the process of negotiating coalition candidate lists for the 2005 legislative elections.