The first chapter examines consumer choices of health insurance contracts. An important innovation in health insurance design is a high-deductible health plan paired with a health savings account (HSA). These contracts aim to control costs by linking insurance coverage with tax incentives for saving, but their rules are highly complex. How consumers perceive the features of these contracts may dampen any cost reduction and produce unintended welfare effects by distorting plan choices. Using a novel administrative dataset linking health insurance choices, medical claims, and saving in HSAs and 401(k)s from a large U.S. health insurer, I develop and estimate a model that integrates HSA saving with deductible choices. I estimate over two-thirds of the marginal HSA dollar is allocated to reduce the deductible, which counteracts the contract's cost-control incentives and leads consumers to choose different insurance plans than they would without an HSA. In this setting, using HSA contributions to offset higher deductibles produced no reduction in health care costs. Several counterfactual analyses quantify the welfare implications of using the HSA to finance current costs on moral hazard, plan enrollment and premiums, and the consumption smoothing benefits from insurance. Health insurance contracts that require sophisticated consumer decision-making may work well in theory, but may be less effective and lead to unintended consequences in practice. The second chapter investigates how status affects health by comparing mortality between Gold and Silver medalists in Olympic Track and Field. Contrary to conventional wisdom, winners die over two years earlier than losers. Analysis of individual Census records of each athlete and his parents suggests that income is the key mechanism: losers pursued higher-paying occupations than winners after the Olympics, while parental earnings in childhood were similar. An athlete’s performance relative to expectations plays an auxiliary role, but is much less important than income. The results suggest that how people respond to pivotal life events can produce long-lasting consequences for health.