In 2008 Oregon allocated access to its Medicaid expansion program, Oregon Health Plan Standard, by drawing names from a waiting list by lottery. The lottery was chosen by policy makers and stakeholders as the preferred way to allocate limited resources. At the same time, it also gave rise to the Oregon Health Insurance Experiment: an unprecedented opportunity to do a randomized evaluation — the gold standard in medical and scientific research — of the impact of expanding Medicaid. In this article we provide historical context for Oregon's decision to conduct a lottery, discuss the importance of randomized controlled designs for policy evaluation, and describe some of the practical challenges in successfully capitalizing on the research opportunity presented by the Oregon lottery through public-academic partnerships. Since policy makers will always face tough choices about how to distribute scarce resources, we urge thoughtful consideration of the opportunities to incorporate randomization that can substantially improve the evidence available to inform policy decisions without compromising policy goals.