Nearly 70 percent of American students enroll in postsecondary education immediately after graduating high school. Yet college and university completion rates remain highly disparate across social and economic groups. White students in the US are 20 percent more likely than Black and Latino students to graduate, and students from high-income backgrounds are roughly five times more likely to graduate than their lower-income peers. As a result, many students leave higher education without a degree, bearing debt that cannot be discharged through bankruptcy. The upshot is that much of the $1.7 trillion in student loan obligations today is held by those who cannot afford to repay it--an immediate crisis for millions of individuals and a looming threat to the US economy. How did we arrive at this juncture? And what should we do from here? For this Policy Dialogue, the "HEQ" editors asked Sara Goldrick-Rab and David Labaree to explore the past, present, and future of pressing issues facing American higher education. Goldrick-Rab is professor of sociology and medicine at Temple University as well as President and Founder of the Hope Center for College, Community, and Justice in Philadelphia. She is also the chief strategy officer for emergency aid at Edquity, a student financial success and emergency aid company, and founder of Believe in Students, a nonprofit distributing emergency aid. Labaree is a past president of the History of Education Society and the Lee L. Jacks Professor Emeritus at Stanford University. Their dialogue takes readers on a quick and heady jaunt across time, across the country, and across almost all institutional types in higher education. "HEQ" Policy Dialogues are, by design, intended to promote an informal, free exchange of ideas between scholars. At the end of the exchange, we offer a list of references for readers who wish to follow up on sources relevant to the discussion.