Some of the recent literature on negotiations at the end of the Cold War regarding German reunification and the North Atlantic Treaty Organization (NATO) has deflected attention from an important policy problem that arose during subsequent deliberations about whether to enlarge the membership of NATO. Newly released U.S. and Russian archival materials highlight this problem very clearly, namely, how leaders manage tradeoffs and uncertainty. Pursuing one set of interests can harm the achievement of other interests. At times, policies take a while to form, adding to uncertainty in relations between countries. This article highlights the ways U.S. President Bill Clinton and his top advisers convinced themselves that they could both enlarge NATO and keep Russia on a Western-oriented track, despite Russian President Boris Yeltsin's repeated warnings to the contrary.