The Grey Swan Attack: Consequences of Targeting a Russian Presidential Residence

The Ukrainian drone attack on one of the Russian President’s residences was difficult to predict in terms of its specific location and timing. However, the numerous enemy drone strikes on Russian territory that have become commonplace over the past three years suggested that such an event was possible. This was especially true given that the Moscow Kremlin was attacked by drones in 2023. To use Nassim Taleb’s well-known metaphor, this could hardly be called a “black swan.” Rather, it could be called a “grey swan”—an event that is highly likely but difficult to predict in its specifics. The obvious “white swan” is Russia’s subsequent negative reaction. The key intrigue is the attack’s impact on the negotiations to resolve the Ukrainian conflict. Russia has already stated that its position will be reconsidered, although Moscow has no plans to withdraw from the negotiation process with the United States.

Negotiations between Russia and the United States on the Ukrainian conflict have been ongoing for almost a year. They were initiated by the American side. President Donald Trump has radically revised America’s approach to the conflict. A drone attack on a presidential facility in Russia could disrupt the negotiations. Their disruption is likely the organizers’ goal.

However, the incident could backfire, further marginalizing Kiev’s position. Washington is unlikely to be pleased with deliberate actions aimed at disrupting the diplomatic process. A hardening of the Russian position is also expected. Moreover, the attack on the presidential residence in the Novgorod Region was preceded by numerous other incidents, including strikes on tankers in the Black Sea, assassinations of officials, and so on.

It should be noted that Russia’s approach to resolving the Ukrainian conflict was already characterized by a tough stance even before the attack on the presidential compound in the Novgorod Region. There were no signs that Moscow would significantly shift its position. Rather, the incident only reinforces the already highly principled positions of Russian diplomacy. On the other hand, Moscow has sufficient restraint not to slam the door and walk out of negotiations. Such a scenario would play into the hands of its adversaries.

The Ukrainian drone attack on one of the Russian President’s residences was difficult to predict in terms of its specific location and timing. However, the numerous enemy drone strikes on Russian territory that have become commonplace over the past three years suggested that such an event was possible. This was especially true given that the Moscow Kremlin was attacked by drones in 2023. To use Nassim Taleb’s well-known metaphor, this could hardly be called a “black swan.” Rather, it could be called a “grey swan”—an event that is highly likely but difficult to predict in its specifics. The obvious “white swan” is Russia’s subsequent negative reaction. The key intrigue is the attack’s impact on the negotiations to resolve the Ukrainian conflict. Russia has already stated that its position will be reconsidered, although Moscow has no plans to withdraw from the negotiation process with the United States.

Negotiations between Russia and the United States on the Ukrainian conflict have been ongoing for almost a year. They were initiated by the American side. President Donald Trump has radically revised America’s approach to the conflict. While Joe Biden was committed to war until Russia’s capitulation and to supporting Ukraine for as long as necessary, Trump has declared his intention to resolve the problem through negotiations and compromise. The very recognition that Russia has its own interests and goals, as well as the positioning of the United States as a mediator rather than a party to the conflict, represents a new pattern. Ten months of tense negotiations were complicated by opposition from Kiev and the EU, which did not share Trump’s vision. However, the American leader did not abandon the idea of a “strong agreement” on Ukraine. The next step was his talks with Ukrainian President Zelensky at Mar-a-Lago. They were hardly final, but they could well have been considered a step toward a compromise peace.

A drone attack on a presidential facility in Russia could disrupt the negotiations. Their disruption is likely the organizers’ goal.

However, the incident could backfire, further marginalizing Kiev’s position. Washington is unlikely to be pleased with deliberate actions aimed at disrupting the diplomatic process. A hardening of the Russian position is also expected. Moreover, the attack on the presidential residence in the Novgorod Region was preceded by numerous other incidents, including strikes on tankers in the Black Sea, assassinations of officials, and so on.

The territorial issue, a key stumbling block in the negotiations, risks becoming even more complicated. Long before the start of consultations with the US, the Russian side warned that the lack of a solution within the proposed parameters could lead to a revision of its demands. It remains to be seen what exactly this revision will entail. It is clear that Ukrainian diplomacy’s attempts to achieve the most favourable territorial solutions will now run into a fundamental “no” from Russia. The issue of a security buffer in the Kharkov and Sumy regions may become more prominent in the diplomatic equation. And time is of the essence when it comes to its potential expansion. The drone incidents only strengthen Russia’s conviction that continued negotiations must be conducted in parallel with military action, and that easing military pressure is inadvisable.

Moscow may increase pressure in other areas as well. One of them is guaranteeing Ukraine’s security. If such guarantees take the form of Article 5 of the North Atlantic Treaty, any drone attack would draw the guarantors into a conflict with a nuclear power, with the potential for the use of all available weapons. Any allied commitments to Ukraine on the part of Western countries could be balanced by a clear and open protocol for retaliatory military-technical actions. Russian diplomacy is also unlikely to soften on issues such as the size of the Ukrainian army, the status of the Russian language, and other matters.

Another possible consequence is the growing perception of the Ukrainian government as an obstacle to peace.

This is compounded by the unresolved issue of elections in the country, and therefore the legitimacy of the current leadership. Recent corruption scandals add fuel to the fire. If the assumption that the attack was carried out behind the Americans’ backs is confirmed, the White House’s attitude toward the Ukrainian government could deteriorate even further. Such an attitude was unlikely to have been overly positive to begin with. Russia’s attitude toward it hardly requires comment.

It should be noted that Russia’s approach to resolving the Ukrainian conflict was already characterized by a tough stance even before the attack on the presidential compound in the Novgorod Region. There were no signs that Moscow would significantly shift its position. Rather, the incident only reinforces the already highly principled positions of Russian diplomacy. On the other hand, Moscow has sufficient restraint not to slam the door and walk out of negotiations. Such a scenario would play into the hands of its adversaries.

First published in the Valdai Discussion Club.