The 2007 negotiations between the United Auto Workers (UAW) and Detroit automakers have focused national attention on a potentially innovative response to the long-term decline in retiree health insurance in the United States. The union agreed that an independent trust called a Voluntary Employees’ Beneficiary Association (VEBA) will assume responsibility for UAW retiree medical care at the three automakers. Other unionized employers now are looking at these so-called defeasance VEBAs as a way to free themselves of burdensome health-care legacy costs. An analysis of the largest one, at GM, suggests that the concept is a second-best option for unions able to retain employer-paid retiree coverage. However, it may be a viable alternative for those unable to fend off unilateral elimination by an employer. Both private- and public-sector unions and employers can draw important lessons from the defeasance VEBA agreed to by the UAW and GM, which will deploy innovative tactics to distribute cost and risk amongst the company, workers, and retirees. More broadly, the new VEBAs illuminate a gaping hole in the federal tax code, which offers few incentives for employees to save for postemployment medical needs even as employers have shifted the responsibility on them to do so. A VEBA is a flexible vehicle that could provide the most tax-efficient savings method for workers whose employer doesn’t offer retiree coverage. However, changes in federal law likely would be required for the concept to become widespread.