President Donald Trump’s Middle East envoy Steve Witkoff is gearing up for another trip to Russia. As Trump’s Friday deadline for a Russian ceasefire in Ukraine looms, Witkoff is trying to contain the scope of US-Russia tensions and lay the foundations for a more peaceful future.
Noble goals, but is Witkoff up to the task? Witkoff’s past visits to Russia create an uncomfortable picture. During a March 2025 interview with Right-wing media personality Tucker Carlson, Witkoff claimed he “liked” president Vladimir Putin and declared: “I don’t regard Putin as a bad guy. He is super smart.”
After meeting with Putin in St. Petersburg on April 11, Witkoff hailed the Russian president’s commitment to a “permanent peace” in Ukraine and expressed openness to ceding all five illegally annexed regions to Russia.
Witkoff’s naivete about Putin’s intentions sowed discord within the Trump administration and shook Ukraine’s confidence in American support. In mid-April, secretary of state Marco Rubio reportedly expressed strong opposition to Witkoff’s willingness to lift sanctions on the shuttered Nord Stream-2 gas pipeline. Ukrainian foreign ministry spokesman Heorhii Tykhyi, meanwhile, fervently objected to Witkoff’s proposal to cede his country’s territory to Russia.
Can Witkoff overcome these negative memories and have an impactful meeting with Putin? Russian commentators are expressing defiant scepticism about Witkoff’s impending trip. Fyodor Vytolovsky, the director of Moscow’s Imemo research institute, told Rossiya-24: “Expecting that we will suddenly come to an agreement with the Americans on everything and that the conflict in Ukraine will be resolved is unfounded and premature.”
This suggests that Putin will use the Witkoff meeting as another opportunity to buy time and stall the progress of peace. Putin’s weekend meeting with Belarusian president Alexander Lukashenko made it very clear that he equates peace with Ukraine’s capitulation and wants to be paid up-front with comprehensive sanctions relief against Russia.
Witkoff can throw Putin off his game with a well-articulated counterpunch that embodies Trump’s espoused principle of peace through strength. While Putin chooses hardline ultra-nationalist former culture minister Vladimir Medinsky as the figurehead for peace talks with Ukraine, he typically uses the smooth-talking Russia Direct Investment Fund (RDIF) chief Kirill Dmitriev as a frontman for engagements with Trump’s team. Dmitriev waxes lyrically about the prospects for post-war US-Russia economic co-operation and dangles Russia’s rare earth metals as an appealing carrot for engagement.
While Witkoff responded positively to Dmitriev’s overtures in the past, he must not take the bait this time. Witkoff should instead articulate America’s desire to impose severe sanctions against Russia if it continues the war and tie their potential relief to a comprehensive peace treaty.
The bipartisan Sanctioning Russia Act of 2025, which was crafted by South Carolina Republican senator Lindsey Graham and Connecticut Democratic senator Richard Blumenthal, provides the ingredients for Witkoff’s rebuttal.
The sanctions bill would provide sweeping punitive measures against Russian banks and institutions that support the war, and threatens 500 per cent tariffs on purchasers of oil, uranium and natural gas of Russian origin.
Witkoff should also underscore America’s commitment to dismantling Russia’s less-discussed sanctions circumvention tactics. Russian nuclear energy giant Rosatom remains connected to Swift and serves as a backdoor financier for the military-industrial complex.
Regional banks and closed mutual funds leverage opaque intermediaries to give sanctioned oligarchs access to the Western financial system. Substantial quantities of Russian timber continue to be shipped to US ports.
Calling out these tactics could shatter Russia’s confidence that it can simply evade the next round of American sanctions with impunity. The US’s legally ensconced secondary sanctions capacity and superior flexibility to the EU’s bloc-wide consensus bolsters the efficacy of these threats.
Witkoff also must pre-empt any escalatory measures that Russia could undertake in response to stiffer sanctions. America must emphasise the need to preserve the safety of Ukraine’s nuclear energy facilities and warn that the detonation of the Zaporizhzhia nuclear power plant could lead to the invocation of Nato’s Article 5.
Further relentless attacks on Ukrainian cities will merely expedite the transfer of American long-range missiles to Ukraine and loosen lingering restrictions on their use against Russian targets. They will also lead to new US-Ukraine security agreements like the impending drone deal that Trump recently discussed with president Volodymyr Zelensky.
Threatening nuclear weapons use against Ukraine or Nato allies will lead to a repetition of Trump’s deployment of nuclear submarines near Russia. Witkoff needs to show Putin that Trump is serious about calling his bluffs and will not tolerate the brinkmanship tactics that Russia used to scare Western countries into backing down.
Even with these assertive responses, Putin is unlikely to change his calculus in the short-term. Trump’s admission that Russia is “pretty good at avoiding sanctions” aligns well with the mood of confidence in the Russian business community. Russia’s proclaimed victory in the Donetsk battleground of Chasiv Yar after a bloody sixteen-month offensive leaves it convinced that it maintains an advantage on the frontlines.
Despite these dynamics, Russia’s war economy is on the verge of recession and staggering military casualties cannot be sustained forever. Putin’s war machine is not an unassailable armada, and strong messaging from Witkoff can make the Russian tyrant more vulnerable than ever.
President Donald Trump’s Middle East envoy Steve Witkoff is gearing up for another trip to Russia. As Trump’s Friday deadline for a Russian ceasefire in Ukraine looms, Witkoff is trying to contain the scope of US-Russia tensions and lay the foundations for a more peaceful future.
Noble goals, but is Witkoff up to the task? Witkoff’s past visits to Russia create an uncomfortable picture. During a March 2025 interview with Right-wing media personality Tucker Carlson, Witkoff claimed he “liked” president Vladimir Putin and declared: “I don’t regard Putin as a bad guy. He is super smart.”
After meeting with Putin in St. Petersburg on April 11, Witkoff hailed the Russian president’s commitment to a “permanent peace” in Ukraine and expressed openness to ceding all five illegally annexed regions to Russia.
Witkoff’s naivete about Putin’s intentions sowed discord within the Trump administration and shook Ukraine’s confidence in American support. In mid-April, secretary of state Marco Rubio reportedly expressed strong opposition to Witkoff’s willingness to lift sanctions on the shuttered Nord Stream-2 gas pipeline. Ukrainian foreign ministry spokesman Heorhii Tykhyi, meanwhile, fervently objected to Witkoff’s proposal to cede his country’s territory to Russia.
Can Witkoff overcome these negative memories and have an impactful meeting with Putin? Russian commentators are expressing defiant scepticism about Witkoff’s impending trip. Fyodor Vytolovsky, the director of Moscow’s Imemo research institute, told Rossiya-24: “Expecting that we will suddenly come to an agreement with the Americans on everything and that the conflict in Ukraine will be resolved is unfounded and premature.”
This suggests that Putin will use the Witkoff meeting as another opportunity to buy time and stall the progress of peace. Putin’s weekend meeting with Belarusian president Alexander Lukashenko made it very clear that he equates peace with Ukraine’s capitulation and wants to be paid up-front with comprehensive sanctions relief against Russia.
Witkoff can throw Putin off his game with a well-articulated counterpunch that embodies Trump’s espoused principle of peace through strength. While Putin chooses hardline ultra-nationalist former culture minister Vladimir Medinsky as the figurehead for peace talks with Ukraine, he typically uses the smooth-talking Russia Direct Investment Fund (RDIF) chief Kirill Dmitriev as a frontman for engagements with Trump’s team. Dmitriev waxes lyrically about the prospects for post-war US-Russia economic co-operation and dangles Russia’s rare earth metals as an appealing carrot for engagement.
While Witkoff responded positively to Dmitriev’s overtures in the past, he must not take the bait this time. Witkoff should instead articulate America’s desire to impose severe sanctions against Russia if it continues the war and tie their potential relief to a comprehensive peace treaty.
The bipartisan Sanctioning Russia Act of 2025, which was crafted by South Carolina Republican senator Lindsey Graham and Connecticut Democratic senator Richard Blumenthal, provides the ingredients for Witkoff’s rebuttal.
The sanctions bill would provide sweeping punitive measures against Russian banks and institutions that support the war, and threatens 500 per cent tariffs on purchasers of oil, uranium and natural gas of Russian origin.
Witkoff should also underscore America’s commitment to dismantling Russia’s less-discussed sanctions circumvention tactics. Russian nuclear energy giant Rosatom remains connected to Swift and serves as a backdoor financier for the military-industrial complex.
Regional banks and closed mutual funds leverage opaque intermediaries to give sanctioned oligarchs access to the Western financial system. Substantial quantities of Russian timber continue to be shipped to US ports.
Calling out these tactics could shatter Russia’s confidence that it can simply evade the next round of American sanctions with impunity. The US’s legally ensconced secondary sanctions capacity and superior flexibility to the EU’s bloc-wide consensus bolsters the efficacy of these threats.
Witkoff also must pre-empt any escalatory measures that Russia could undertake in response to stiffer sanctions. America must emphasise the need to preserve the safety of Ukraine’s nuclear energy facilities and warn that the detonation of the Zaporizhzhia nuclear power plant could lead to the invocation of Nato’s Article 5.
Further relentless attacks on Ukrainian cities will merely expedite the transfer of American long-range missiles to Ukraine and loosen lingering restrictions on their use against Russian targets. They will also lead to new US-Ukraine security agreements like the impending drone deal that Trump recently discussed with president Volodymyr Zelensky.
Threatening nuclear weapons use against Ukraine or Nato allies will lead to a repetition of Trump’s deployment of nuclear submarines near Russia. Witkoff needs to show Putin that Trump is serious about calling his bluffs and will not tolerate the brinkmanship tactics that Russia used to scare Western countries into backing down.
Even with these assertive responses, Putin is unlikely to change his calculus in the short-term. Trump’s admission that Russia is “pretty good at avoiding sanctions” aligns well with the mood of confidence in the Russian business community. Russia’s proclaimed victory in the Donetsk battleground of Chasiv Yar after a bloody sixteen-month offensive leaves it convinced that it maintains an advantage on the frontlines.
Despite these dynamics, Russia’s war economy is on the verge of recession and staggering military casualties cannot be sustained forever. Putin’s war machine is not an unassailable armada, and strong messaging from Witkoff can make the Russian tyrant more vulnerable than ever.