Background/Context This article introduces the special issue on reimagining research and practice at the crossroads of philosophy, teaching, and teacher education. The authors provide an overview of previous research at this “crossroads” and describe how the special issue collaborators have sought to chart fresh ground in light of current practical and policy challenges that teachers and teacher educators face. Purpose/Focus of Study The project that gave rise to the special issue emerged from a self-study, conducted by the first two authors, of the Program in Philosophy and Education at Teachers College, Columbia University. They have been rethinking the place of philosophy in teaching and teacher education, while also re-examining the place of teaching and teacher education in philosophy. They see opportunities for creative work at the “crossroads” of these fields of practice and inquiry, while also appreciating the numerous pressures in our era on educators to adopt an unnecessarily narrow, economics-driven agenda. To pursue this interest, they organized a conference whose participants are the authors of what follows in this issue. Setting/participants The organizers invited six graduates of their program, who focus on teaching and teacher education, to participate in an intensive, two-day conference that would address prospects for re-envisioning generative work at the “crossroads.” They asked each graduate (now a tenure-track or tenured professor) to invite a colleague rooted in other disciplinary configurations—but also invested in teaching and teacher education—to collaborate with them. The conference featured six presentations by these teams of colleagues, who are, in turn, the co-authors of the six core articles included in this special issue of the journal. The faculty organizers also invited two senior scholars steeped in teaching and teacher education to work with them as commentators before, during, and after the conference. Project Design In preparation for the conference, held at Teachers College on November 9–11, 2017, the 17 participants devoted approximately eight months to extensive collaborate work, including the construction of a conference bibliography that would inform their work. During this time, each team of future co-presenters/ co-authors (a) conceived a topic they would examine together, (b) prepared an initial outline of their planned inquiry, and (c) composed a draft of their forthcoming co-presentation at the conference. At each of these stages, the two senior faculty in Philosophy and Education at Teachers College, and the two invited senior faculty, provided critical commentary. After the conference, the co-presenters transformed their work into articles. This process included several pre-established rounds of critical commentary on drafts by the senior faculty. The upshot of this collaborative endeavor are the studies presented in this issue: (1) a philosophical perspective on what are called “core practices” in teaching, (2) the philosophical underpinnings of an approach in teacher education entitled “Interruptions,” (3) what it means to think of teachers as “handlers” of student and community memory, (4) reimagining childhood, and what it means to work with children, through the fused lens of philosophy and practice, (5) teaching and teacher education understood as racialized pedagogies, and (6) how educators can expand conceptions of what it means to succeed in society. Conclusions/Recommendations The authors elucidate ramifications for research and practice of our collaborative work at the crossroads of philosophy, teaching, and teacher education. They address why ethical insight is as vital an outcome of research at this crossroads as is newly minted knowledge. They spotlight philosophy's dynamic place in the practices of teaching and teacher education, including how it can help us reconceive the very idea of “good” practice. The authors suggest that philosophy need not be “applied” to education, as if philosophy and action inhabit different worlds, because educational work is always already saturated with philosophical questions and considerations, whether practitioners identify them in such terms or not. Put another way, the authors show how educational practice can transform philosophers’ understanding of the purposes and scope of their field. They argue that philosophers, scholars of teaching, teacher educators, and teachers all have an indispensable custodial or stewardship role to play in education. They are the people best positioned to care for both the practice of teaching and its practitioners. As such, it is important for them to sustain a meaningful, collaborative conversation, especially in the present context of worrisome political trends and continued pressure on educators to narrow their remit in the face of economic and other non-educational considerations.