THE COUNTDOWN for settling Ukraine’s geopolitical position within Europe and greater Eurasia is entering its final stages. Barring his resignation or removal from office, the denouement will occur under the watch of Ukraine’s populist-comedian president, Volodymyr Zelensky. Zelensky and his “Servant of the People” political movement won an overwhelming mandate from Ukrainian voters in 2019 by promising to succeed where Zelensky’s immediate predecessor, Petro Poroshenko, and the Ukrainian political establishment (which was largely voted out of office) had failed: to settle the conflict with Russia while presiding over Ukraine’s eventual integration into the Euro-Atlantic world. Time, however, is not on his side. Barring a last-minute miracle, Russia’s longstanding effort to bypass Ukraine as its conduit to Western markets will be completed, while changes in both European and American political priorities and strategic assessments may diminish the importance and relevance of Ukraine as a central component in relations between Russia and the West.

When the Soviet Union collapsed in 1991, Ukraine, the eponymous “borderland” between Russia and Central Europe, emerged as the principal bellwether of the temperature of relations between Moscow and the West. From the disposition of Ukraine’s Soviet nuclear weapons legacy to the stability of Russian energy supplies to Western European markets, from the formulation of the European Union’s (EU) wider neighborhood policy to the prospect of NATO’s eastern enlargement, the health of the Russia-Ukraine relationship could not be separated from the type of partnership Russia could realistically forge with the United States and Europe. Given Ukraine’s geographic realities—its northern and eastern borders nestled right up against the soft underbelly of the Russian Federation, and its western marches—courtesy of Josef Stalin’s postwar shifting of borders—controlling the access points into the heart of Europe—neither Moscow nor NATO could be indifferent to Ukraine’s ultimate geostrategic alignment.

FOR THE last thirty years, U.S. policy towards Ukraine has been guided by former National Security Advisor Zbigniew Brzezinski’s aphorism: a Russia with Ukraine is an empire (and by extension, a threat to the security of the Euro-Atlantic area), but a Russia without Ukraine has the chance to become a “normal” nation-state (and, by implication, is better “balanced” vis-à-vis the principal European powers of France, Germany, the United Kingdom and Italy). While this created a clear imperative for the United States to oppose Ukraine’s absorption into some sort of greater Russia, it left unclear whether it was necessary—or worth the cost—for Ukraine to be brought fully into the Western security structure, or whether the American strategy for Euro-Atlantic security could be secured by Ukrainian neutrality. For its part, post-Soviet Russia, even during the heyday of the Atlanticists during the first Yeltsin administration, always drew a bright shining line at Ukraine’s entry into NATO (unless Russia was also a member). Even when recognizing Ukraine’s political independence, Russia maintained that Ukraine’s cultural and economic links necessitated a special relationship between Moscow and Kiev.

Had post-1991 Ukraine been led by presidents in the geopolitical image of Kazakhstan’s Nursultan Nazarbayev, Ukraine might have embraced the benefits of positioning itself as the keystone state connecting the Euro-Atlantic and Eurasian worlds. As a Euro-Atlantic bridge, Kiev could have avoided a security dilemma with Russia but used its leverage—since in the aftermath of the collapse of the ussr Ukraine remained Russia’s primary linkage to the West—to deal with Russia from a position of strength and near-equality. But the vicissitudes of Ukrainian domestic politics prevented this from happening. First, there was the geographic divide within the country between the southeastern regions, which wanted to maintain close economic and political ties with Russia, and the west, which wanted to break Ukraine once and for all out of the Russian embrace. At the same time, the Ukrainian economic oligarchy mouthed slogans promising reform and the achievement of the country’s European destiny but was more than happy to become enmeshed in corrupt deals with Russian entities. Whereas the Baltic States took very hard and painful measures to reorient their economies away from Russia—and, in turn, Russia rerouted its own export infrastructure away from the Baltic States towards a new St. Petersburg-Vyborg corridor—Ukraine was content to remain addicted to cheap Russian energy and subsidies. To paraphrase Robert Kaplan’s assessment of Greek politics, Ukraine was hoping to continue its affair with Russian money while seeking a formal marriage with the West.

As long as Central Europe itself remained outside the Euro-Atlantic world, Ukraine’s own dalliances were less critical. By 2004, however, the integration of Central Europe into both the EU and NATO brought the border of the Euro-Atlantic world squarely against Ukraine’s western frontiers. The assessment, including a famous article in these very pages at the dawn of the new millennium, was that Russia was “finished” as a great power. This led to calculations that the inexorable eastward enlargement of the West would continue without imposing any major costs on the United States or Western Europe—and without provoking a major reaction from Moscow. At the same time, the sense that Ukraine could find itself on the wrong side of a new dividing line in Europe—and that Ukraine’s European dream was in danger from a corrupt elite who benefited from Moscow’s largess—helped to fuel the 2004 Orange Revolution, which brought Viktor Yushchenko to power. Yushchenko and his erstwhile ally, Prime Minister Yuliya Tymoshenko, made it clear that they wished to end Ukraine’s borderland status in favor of Ukraine becoming the eastward redoubt of the Euro-Atlantic world.

The Orange Revolution (along with the Rose Revolution in Georgia the preceding year) fundamentally changed the tenor of U.S.-Russia relations and strained Russia’s ties with Europe. From 1991 until 2003, it was routine for Russian and American officials to proclaim that the Cold War was over and that the two countries enjoyed a strategic partnership. The EU, particularly under the leadership of EU Commission president Romano Prodi, had also sketched out a vision of EU-Russia cooperation that would fulfill Charles de Gaulle’s vision of a Europe stretching from the Atlantic to the Urals (or Vladivostok, by extension). But after 2004, there was now a government in Kiev that was demanding that NATO and the EU live up to their claims that any European state could join—and was asking for political, economic and even military assistance to secure Ukraine’s freedom to choose against the levers that Russia could deploy to stop Ukraine’s westward movement.

From this point onward, the Ukraine issue could never be segregated from other aspects of the U.S.-Russia relationship. There was no basis to “agree to disagree.” For the United States to comply with Russian demands that Ukraine be Finlandized as a permanent neutral would be a tacit admission that the open door of the Euro-Atlantic world to new members was not so open, and that Washington was prepared to recognize a de facto Russian sphere of influence in the former Soviet space. All other items on the bilateral agenda—counterterrorism, stopping the Iranian nuclear program, energy cooperation and so on—gradually became subordinated to the unresolved tensions surrounding Ukraine. Moreover, the first waves of EU and NATO enlargement changed the center of gravity in both organizations. Germany had pushed for enlargement so that its eastern border would not be the frontier of the European world. But now Poland and other Central European states were similarly interested in changing their position—from being Euro-Atlantic frontline states to shifting that line further east.

After 2004, Russia adopted new strategies. It began to explore ways to reduce Ukraine’s role as Russia’s conduit to Europe, leading to a new pipeline project (Nord Stream) that would connect the recently-constructed energy export infrastructure in St. Petersburg directly to Germany. It strengthened its capabilities to involve itself in Ukrainian politics, particularly via the “Party of Regions.” With the Orange Revolution having deprived Russia of friendly elements at the national level of governance, Moscow’s approach shifted to pushing for the decentralization of power in Ukraine, ensuring that pro-Russian regions would be able to exercise veto power over the country’s foreign policy (and so forestall Ukraine’s ability to eventually join NATO and the EU). Russia also promoted new efforts to strengthen Eurasian integration and lock the former Soviet states into those arrangements.

At the same time, Moscow, having seen that European-level institutions were less well disposed to Russia, intensified efforts to deal bilaterally with its major European partners and, whenever possible, find ways to exclude EU involvement by stressing the importance of national sovereignty. Finally, Moscow stepped up its efforts to probe how strong the rhetorical American commitment to countries like Ukraine and Georgia would be in the event of clashes breaking out—both to judge the efficacy of the American response and demonstrate, as far as possible, the hollowness of any American guarantees. All of this culminated in the Russia-Georgia clash in August 2008—which indeed exposed the limits of Western promises and the circumscribed nature of their response.

FOLLOWING THE Georgian war, French president Nicolas Sarkozy, and later, newly-elected U.S. president Barack Obama initiated so-called “reset” efforts to back away from a more confrontational stance between Russia and the West. Ukrainian elites took notice. Former Ukrainian president Leonid Kuchma drew the following conclusion after watching the “say-do” gap in the Western response to Georgia: “Is there anyone [who] really thinks we need to tilt against Russia and someone will take our side? I’m sure that neither [the] EU nor the U.S. won’t lift a finger.”