Health insurance for individuals classified as obese is a topic of ethical debate given the rising costs of premiums and the pressures of an unstable health economy. Difficult questions arise relative to health insurance and coverage for obese populations. For instance, do the chronic disease claims, attributed to individuals classified as obese, cause an inequitable rise in the cost of healthcare to normal-weight populations? Facts indicate an increased cost of care for obese populations compared to normal-weight populations. Health insurance is a complex service industry with multiple stakeholders, which give rise to ethical uncertainty in fidelity, veracity, and social responsibility, especially since insurance is a business that must generate profit to sustain itself. It is important for health policy makers to consider variable ethical philosophies when designing legislation that guides health insurance coverage for populations classified as obese. Utilitarian and libertarian philosophies are used to compare viewpoints relative to health insurance policy for the obese in the United States. These philosophies contrast the “good for all” versus the “right of the individual” in ethical decision making for health policy. The context of health insurance as a foundation for moral debate health about healthcare of obese populations is presented and debated herein.