While it might currently be challenging to imagine Russia as a NATO member, a change to the future strategic context could make it equally difficult to imagine Russia outside of NATO. The historical analysis of NATO enlargement during the past sixty years yields insights into the operational consequences associated with the possible addition of Russia to the Alliance. The technical details of incorporating new members into the Alliance have remained relatively constant during the past sixty years. In addition, changes in the strategic context have continually redefined the feasibility and acceptability of NATO enlargement. However, factors specific to Russia present unique benefits and challenges that merit consideration prior to NATO extending the invitation to join the Alliance. Russia's status as a great power could influence how it interacts with NATO and how the Alliance functions. The extension of NATO into Asia and the associated extension of the Article 5 security guarantee brings risk and opportunity for the Alliance. Indeed, extension into Asia may provide the interlocutor that is necessary to deal with adversarial regimes.