This year’s edition of Hopes, Fears, & Reality explores the broad realities of the present-day charter school movement. In this chapter, Lydia Rainey, Andrew Rotherham, and Paul Hill report on the results of an animated discussion between charter school leaders and teachers union leaders. (The 2006 symposium brought the two groups together to discuss areas of agreement and disagreement around teachers unions and public charter schooling.) The authors show that even though the two groups harbor a deep and abiding distrust of each other, some leaders on both sides believe that a period of détente could be in their own interest. The chapter suggests ways the two sides can begin to build mutual confidence, reduce hostilities, and structure some early collaborative efforts between unions and charters.