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Accusations of illegality have dogged the Obama Administration's efforts to implement the Affordable Care Act (ACA), the most ambitious piece of social legislation since the advent of Medicare and Medicaid. Some of the accusations have merit; indeed, it would be surprising if they did not. Even as the ACA's rollout has exposed unanticipated difficulties in the statutory design, congressional antipathy to health reform has precluded looking to the legislature to iron out those difficulties. To secure his principal achievement, President Obama has repeatedly tested the limits of executive authority in implementing the ACA. Six years after its enactment and two years after its full implementation, now is an auspicious time to take stock. Moving past the partisan bickering, to what extent has the Obama Administration skirted the law or broken conventions to implement the ACA? In what ways, if any, has the messy implementation process set worrisome precedents? How troubled should we be if the Administration has at times brushed up against and even exceeded the limits of its power? To get traction on these questions, this Article takes a close look at the most hotly debated legal questions surrounding the ACA's rollout. The selections reflect my own judgments about the most serious allegations of executive impropriety, but they are not idiosyncratic: they closely track-and indeed go beyond-the selections made by those seeking to demonstrate the President's disregard for law. My hope is that a holistic and even-handed examination of the Administration's purported legal excesses will provide a useful focal point for understanding how law restrains executive discretion in a time of polarized politics. The Article closes with some thoughts about the status of executive lawbreaking in American constitutional culture and how to discipline such lawbreaking when it occurs.