Rational choice theories of education view student's educational decision as a sequence of binary choices between options that entail long-term utility and options that reduce short-term risk of failure. One of the best articulated models of educational choice asserts that choice between alternative options is affected by students' utility considerations, their expectations regarding the odds of success or failure in alternative educational options, and their motivation to avoid downward social mobility. We evaluated these propositions using data on students' curricular choices in Tel Aviv-Jaffa high schools. We found that educational choice was affected by subjective utility and failure expectations, but not by class maintenance motivations. Just as important, and contrary to the model's main assertion, educational inequality between social strata was not mediated by any of these choice mechanisms. Finally, and importantly, about a fifth of the students in Tel Aviv-Jaffa did not choose between long-term utility and short-term risks, but combined the two. These students, the hedgers, combined the riskier scientific subjects that are expected to yield long-term utility with social sciences and the humanities that reduce the risk of failure in the short term, but are not expected to yield large long-term utilities. The hedgers, moreover, were shown to be disproportionately female and drawn from disadvantaged social strata. These results suggest that educational systems that allow multiple rather than alternative choices may enhance the attainment of working-class youth because they enable them to opt for long term utility while providing a safety-net in the form of additional safer subjects.