A week after CIA director John Ratcliffe paid a secret visit to Moscow, and as Chinese, Russian and Iranian leaders met at the Shanghai Cooperation Organisation’s (SCO) Bishkek Summit, U.S. President Donald Trump’s diplomatic envoys, Steve Witkoff and Jared Kushner, arrived in both Russia and Ukraine. Received by Russian President Vladimir Putin and Ukrainian President Volodymyr Zelenskyy, the delegation described the visits as encouraging, positive and constructive. Still, far more questions than answers remain concerning the true nature of the Witkoff-Kushner mission.
At first glance, this diplomacy appears to be an attempt to gauge whether both warring parties are determined to sustain full-scale combat through the coming winter. Now increasingly unavoidable, this winter campaign will be remarkably tough for both sides for much the same reasons. The ongoing war of attrition is reaching its structural limits; Moscow and Kyiv urgently require robust air defenses, anti-drone systems, troop replacements and energy security to maintain their campaigns during the winter months. Despite these severe constraints, neither party is close to ending the conflict before fully realizing its core war objectives.
Today, Russia continues to hold nearly one-fifth of Ukrainian territory, while Kyiv’s immediate aim is to stall Russian forward advances at a tactical level. That tactical objective appears to have been achieved, given that Russian progress in the Donbas region remains extremely limited. On the other hand, Kyiv’s overarching strategic ambition – expelling Russian forces from occupied territories and securing sustainable guarantees against future aggression – remains unfulfilled. Meanwhile, the Kremlin insists that Ukraine must relinquish the remainder of the Donbas still under Kyiv’s control, reduce the size of its military and defense capabilities, purge nationalist militia units, and commit to permanent neutral status. Even if both nations sustain their military operations at the same pace throughout this winter, there is no guarantee that either will move any closer to achieving these war aims.
Furthermore, the economic toll of this war of attrition is escalating rapidly for both sides as they engage in mutual economic warfare. Russia has repeatedly targeted Ukrainian ports, rail networks, energy infrastructure and key logistics warehouses along vital export routes such as Odesa, while Ukrainian forces occasionally strike vessels belonging to Russia’s shadow fleet, alongside warehouses and oil refineries. In this high-stakes energy warfare, Kyiv’s wild card remains European and broader Western backing. However, to date, Western actors have failed to strangle the Russian economy in any full-fledged sense. The recent SCO summit served as stark proof of this reality. Moscow remains central to North-South transit corridor plans, whilst Beijing has explicitly ensured that bilateral trade – including the supply of dual-use technologies – will continue uninterrupted.
To be sure, the White House has periodically imposed stiffer sanctions and economic pressure on Russia aimed at compelling Moscow to terminate the war. However, with the U.S. currently bogged down in the Straits of Hormuz crisis and initiating another campaign of economic warfare against Iran, the Trump administration needs to constrain Russian assistance to Tehran whilst controlling the escalation trap in the Russo-Ukrainian conflict. Consequently, Washington may be planning to deploy economic incentives to motivate the Kremlin to sit at the negotiating table with the Ukrainians. Notably, during Witkoff and Kushner’s visits to Russia and Ukraine, officials from the U.S. Department of the Treasury were also part of the delegation. This has been widely interpreted as an indication that ongoing economic sanctions on Russia formed an integral part of the talks.
It is not merely the diplomatic atmosphere surrounding the SCO summit, but also the realities of the Russo-Ukrainian escalation spiral, that may be motivating this latest American probe into whether a trilateral meeting on the conditions for a sustainable peace is achievable. Time is working against both Ukraine and Russia. The probability of achieving their definitive war objectives during this winter period is ambivalent at best. Hence, both capitals may be coming closer to contemplating the unthinkable.
There remain numerous unthinkable steps yet to be taken in both sides' war efforts. Observers are already familiar with Russian threats to nuclearize the conflict, as well as warnings to target European military assets in Ukraine and elsewhere should Moscow determine that European actors are behind attacks on Russian sovereign assets. Moscow is hardly reckless enough to confront NATO’s superior conventional capacity directly; however, in the realm of sub-strategic, asymmetric and hybrid warfare, the Kremlin can disturb European security from multiple angles. Recent incidents – such as the German-Russian drone crisis, Swedish allegations regarding Russian support for radical political parties in upcoming elections, and Spanish accusations concerning Moscow's role in the Ceuta migrant crisis – demonstrate that Europeans still fall short of confronting these asymmetric challenges successfully.
The Trump administration sheds no tears over European anxieties in the face of the Russian challenge. Nevertheless, the White House has seized an opportunity, recognising that every actor engaged in this conflict is calculating the rising risks and financial costs of continued fighting through the winter.
The timing of the Trump administration’s latest test of Russian and Ukrainian willingness to negotiate is astute. The primary problem, however, is that there is still no sign of a shift in the strategic mindset of either Moscow or Kyiv.
