Anchor movements rest on the premise that people- and place-based initiatives can be mutually reinforcing. The community development movement, however, has been haunted for years by the people-place dilemma -- the idea that efforts to help people harm efforts to uplift places and vice versa. Most of the literature on the anchor strategy has focused on one horn of the dilemma, namely, the problem that revitalizing a place may lead to rising housing costs that burden and ultimately displace longtime lower-income residents of the neighborhood. In this article, we examine the other horn of the people-place dilemma -- that helping people in disinvested communities may enable them to move elsewhere, leaving behind poorer communities. We examine this issue through a case study of the St. Louis Anchor Action Network (STLAAN), a collaboration of 16 anchor institutions. St. Louis is a classic legacy city that once enjoyed rapid growth but is now characterized by a falling population and high poverty. We document longstanding trends that have drained STLAAN's focus geography of people and resources, as well as more recent growth of an "eds and meds" economy that presents an opportunity to address decades of disinvestment and decline. We document STLAAN's efforts to invest in its focus geography and the people who live there and conclude with research proposals that could help guide anchor initiatives facing similar challenges.