Over the past decade, there has been a deepening interest in youth and adult postsecondary transitions, be these from school to work or from high school to college. This work, based on a wealth of evidence and numerous programs, has developed a variety of best practices for improving students' transition experiences and success in the workforce, with a particular emphasis on disadvantaged, underrepresented youth. Yet much of this work presumes that the current inequality that exists among students in U.S. schools is simply the product of a lack of evidence-based policy solutions. This perspective ignores the important structural and historical factors that have shaped and continue to affect the educational opportunities available to individuals who grow up in poverty. Policy solutions meant to address this inequality must be based on rigorous evidence but also take into account the political forces aligned against addressing this long-term and persistent structural problem within American society. (Contains 5 footnotes.)