WASHINGTON, DC – As President Volodymyr Zelensky sprints through European capitals hunting for unity and firm security commitments, another mission is drawing equal – and far more anxious – attention: real-estate mogul-turned-diplomatic envoy and Trump confidant Steve Witkoff’s return trip to Moscow.
He lands Tuesday with a slimmed-down peace proposal in hand and sky-high expectations back home, but almost zero optimism anywhere else.
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Inside Washington and across European capitals, officials describe a deepening unease: This visit is unlikely to unlock peace, they say, and far more likely to lock the US into a Russian-designed diplomatic holding pattern.
“A waste of time and a diplomatic misstep,” says Yuriy Boyechko, CEO of the US-based Hope For Ukraine.
Speaking to Kyiv Post on Monday, Boyechko said Witkoff’s previous missions “have consistently failed to produce tangible breakthroughs, with the Kremlin merely using the meetings as an opportunity to buy time and stall progress.”
Russia’s strategic intent, he warned, has never shifted: “to ‘devour’ Ukraine and expand its control in Europe.”
Any peace blueprint that emerges from such talks, he added, is “a short-term tactical maneuver, not a genuine commitment to ending the war.”
A plan rewritten – and still rejected
Witkoff arrives in Moscow carrying the latest version of a peace proposal re-drafted by Trump officials along with Ukrainian negotiators – a plan repeatedly downsized after weeks of bruising transatlantic negotiations.
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What began as a 28-point vision – dismissed as the Kremlin’s wish list – is now roughly 19 points, stripped of the “hard issues” and punted to future talks.
But even in its reduced form, Moscow has shown no signs of budging, according to Stephen Sestanovich, a senior fellow for Russian and Eurasian studies at the Council on Foreign Relations.
Speaking at a CFR event on Monday, the analyst said that Russia continues to insist on territorial concessions, constraints on Ukraine’s military, and a renegotiation of NATO’s role in Europe.
As many Russia watchers in Washington note, the Kremlin hasn’t moved “on a single point” since last year’s now-infamous Alaska meeting.
Witkoff, despite being the Trump adviser Moscow most often entertains, has been unable to alter that stance “on anything at all,” one senior European diplomat told Kyiv Post.
Putin wants the meeting, not the deal
Here’s the uncomfortable truth shaping Washington’s mood: Putin wants this meeting, but not because he wants peace.
Moscow is eager to transition the process into a “normal diplomatic” format – committees, technical talks, endless working groups – the very structure that lets Russia stretch negotiations across years. That approach directly contradicts Trump’s instinct for a quick, camera-ready settlement.
Yet Russia’s interest in dialogue isn’t a sign of strength. It’s a reflection of strain.
As Thomas Graham, former Special Assistant to President George W. Bush points out, Russian forces are absorbing “horrific losses for marginal gains,” and the economy is buckling under pressure. If both sides are inching toward talks, it’s because the status quo is becoming unsustainable.
Putin also has a second objective, according to analysts: restoring US–Russia dialogue on broader strategic issues – the Arctic, missile defense, European security – where even symbolic engagement with a US president offers the global stature he craves.
That prestige, Graham argues, remains one of Washington’s least-used sources of leverage.
Boyechko’s warning cuts to the core of the unease coursing through Western capitals: Witkoff may be the wrong messenger at the most dangerous moment of the war.
“Sending an envoy with limited diplomatic background and a known tendency to operate outside typical protocols only empowers Moscow,” he warned.
It lets the Kremlin flood the field with initiatives “that ultimately alter nothing.” Worse, these missteps undercut the seriousness of Washington’s position – and heighten anxiety in Kyiv and across NATO’s eastern flank.
Moscow knows exactly how to exploit that dynamic: In a previous visit, Witkoff was forced to wait eight hours before seeing Putin – a textbook Russian power play disguised as diplomacy.
Europe pushes for relevance
While Washington worries about Witkoff’s next misfire, European governments, meanwhile, are scrambling to shore up Kyiv’s security.
Some capitals are openly discussing the once-taboo possibility of deploying European troops to western Ukraine – a step they argue may be the only way to offset concessions Trump could pressure Kyiv to accept elsewhere.
Yet as Liana Fix, CFR’s Senior Fellow for Europe, cautions, even these moves are being misinterpreted. There is no meaningful NATO-style Article 5 guarantee on the table.
And Russia’s alleged willingness to tolerate Ukraine’s potential EU membership is misdirection: Moscow assumes the EU will never actually manage to integrate Ukraine – and sees EU accession as worthless without NATO.
For Zelensky, facing battlefield shortages and relentless Russian bombardment, these questions aren’t theoretical. They are existential.
Europe’s mood has hardened. Having become the largest overall financial backer of Ukraine, EU and NATO capitals insist they will no longer be cut out of the war’s diplomatic endgame.
The Trump team’s early proposals set off alarms across Europe, particularly a plan to create a US–Russia investment fund from frozen Russian assets, which many see as diverting resources already committed to Ukraine’s reconstruction.
Another red flag was draft language positioning the US as mediator between NATO and Russia, a move frontline states fear could undermine NATO’s core deterrence mission.
Layered on top of those concerns is something deeper: uncertainty about Trump’s strategic worldview. European officials say they still can’t determine whether Washington’s long-term posture will be transactional, isolationist, or something else entirely.
Fix adds a further warning. Washington’s recurring negotiation loop – Russia disappoints, Washington escalates, Congress responds with sanctions, then a new diplomatic push begins – is eroding European confidence in NATO itself. Each cycle, she argues, “allows Russia to bite away” at trust in American commitment.
The leverage question
One of the most contentious debates inside Washington is whether the US should increase pressure on Russia while negotiations unfold.
Graham argues yes: Russia negotiates while fighting; the US should too. That means more arms, more air defenses, and a clear message that broader US-Russia talks are off the table unless Russia shifts on Ukraine.
But Sestanovich delivers a blunt assessment: Trump may not realize he’s being played. Russia, he warns, is “tapping him along.” The White House must stop imagining itself as a mediator and instead behave like an interested party supporting Ukraine.
Only then can Washington reset the balance of power and escape the “endless series of Witkoff–Dmitriev conversations” that create motion without momentum.
Boyechko’s critique reinforces that point: As long as Moscow can manipulate the envoy, the process will stay stuck.
Stagecraft, not statecraft
No one expects Witkoff’s meeting to produce a breakthrough. Not the analysts. Not the Europeans. Not Kyiv.
Putin is unlikely to accept or reject the plan outright. Instead, he’ll push for technical talks and test how much patience Trump has for a slow-roll diplomatic process.
Europe will fight to ensure Ukraine isn’t blamed if things fall apart. Ukraine will try to avoid being painted as the obstructionist.
And, as Fix predicts, “two or three weeks from now,” Western capitals are likely to be right back where they started: frustrated with Russia, debating new sanctions, and worrying about NATO’s long-term credibility.
Into this geopolitical minefield walks Steve Witkoff – Trump loyalist, real-estate mogul, and the most unlikely point man for the most complex diplomatic challenge of the war.
Trump wants a quick win. Putin wants legitimacy and time. Europe wants reassurance that it won’t be sidelined. And Ukraine wants one thing most of all: not to be blamed if this all collapses.
Boyechko’s bottom line is the harshest yet: “Until Russia signals genuine willingness to negotiate – not power plays, not delays – this sixth face-to-face visit will amount to little more than a photo-op for Moscow.”
For Zelensky, sprinting across Europe to shore up support, the stakes could not be higher.
In one of his bleakest warnings yet, he said Ukraine may soon have to choose between “dignity and US support.”
For now, he’s doing everything possible to avoid having to make that choice.