The American Dream: Will Putin and Trump meet in Istanbul, and how dangerous is this meeting for Ukraine?

Trump's spectacular plan

Trump's remark that he may be in Istanbul on Thursday, 15 May, where Vladimir Zelensky has already promised to wait for Vladimir Putin, adds another layer to the diplomatic intrigue of recent days – but it only appears unexpected at first glance.

In reality, the dramatic plan envisioning Trump meeting Putin along the way during his first foreign tour and achieving a diplomatic breakthrough by cutting the Gordian knot of the Russia-Ukraine war has existed since at least early February. Trump himself mentioned the possibility of such a meeting on 12 February, during his first foreign visit to Saudi Arabia, immediately following his initial phone conversation with Putin. At the end of March, sources at Axios, reporting on Trump’s upcoming visit to Riyadh, noted that the visit had been discussed during negotiations between Russian and American delegations on 18 February in the same city and was meant to take place only after a ceasefire agreement in Ukraine.

It is easy to see why this scenario would be highly appealing to Trump. It is possible that its dramatic nature largely influenced his strategy of making concessions to Moscow and abandoning pressure on the Kremlin, which had been part of the initial plan of Keith Kellogg, the special representative for Ukraine (→ Re:Russia: Three Hundred Days in Search of a Silver Bullet). In late March and early April, after negotiations in Riyadh stalled and Russia intensified its bombardment of Ukrainian cities, Trump initially threatened the Kremlin with harsh measures, but within days, he sent Steve Witkoff, a key advocate for concessions to Moscow, to Russia.

Following Witkoff’s first round of negotiations in Russia on 17 April, Putin’s foreign policy adviser Yuri Ushakov casually mentioned the possibility of a meeting in Riyadh, adding that it was an initiative of the American side. However, Washington’s response to Witkoff’s second visit disappointed the Kremlin, and negotiations seemed to enter a pause. On 24 April, when asked whether he might meet Putin during his visit to the Middle East, Trump was vague, saying it was possible but unlikely, and that the meeting would more likely happen after his trip. On 5 May, Putin’s press secretary stated that his boss had no plans to visit Saudi Arabia. Around 10 May, NBC sources within the Trump administration suggested that the meeting would only be possible if a ceasefire was established in Ukraine. However, prospects for this seemed bleak.

Against this backdrop, the potential meeting of the three presidents in Istanbul is less a new development and more a modification of the originally envisioned dramatic conclusion to the negotiation marathon in Riyadh.

Ping-pong between three

It is interesting that on the same day, i.e. 10 May, when NBC sources expressed doubt about the possibility of a ceasefire agreement and a meeting between Trump and Putin, four European leaders – Macron, Starmer, Merz, and Tusk – unexpectedly arrived in Kyiv and issued an ultimatum to Russia, demanding an immediate 30-day ceasefire. Two days earlier, Trump had posted that ‘the United States calls for, ideally, a 30-day unconditional ceasefire... If the ceasefire is not observed, the United States and its partners will impose additional sanctions.’ The initiative of these five leaders essentially expanded on this idea but in a more forceful manner.

There are two fundamentally different tracks for any peace negotiations. The first involves the parties agreeing, with the mediation of a third party, on the conditions for ending hostilities and then, once a general peace agreement is reached, signing a ceasefire deal. The second track follows the reverse order: an unconditional ceasefire becomes the initial step of the negotiation process, and, in this atmosphere of ‘silence’, the parties negotiate and gradually bring their positions closer. Thus, these two approaches differ in what drives the negotiation process – whether the ceasefire is the result or the foundation.

ince February, Trump had insisted on the second approach: a ceasefire as the starting point for negotiations. Moscow, while not outright rejecting this idea, formulated during the first Russia-US meeting in Riyadh, insisted on ‘nuances’ that had to be agreed upon beforehand. As a result, it managed to pull the Trump administration into talks about peace conditions, effectively reversing the order of the negotiation process. By late April, these negotiations had reached a deadlock. Essentially, Moscow’s position was that the condition for a ceasefire was the fulfilment of its maximalist demands on Ukraine, first articulated at the outset of the conflict. Against this backdrop, the Kyiv ultimatum issued by Zelensky and the four European leaders appeared as another attempt to push the Kremlin back toward the second negotiation track.

President Putin responded just a few hours later, on the night of 11 May, an extraordinary event, as he rarely holds late-night press conferences. By making journalists wait an hour and a half for his appearance in order to create maximum hype around his speech, he effectively rejected the coalition's demand for a ceasefire and proposed starting direct Russian-Ukrainian talks in Istanbul, which would be a continuation of the talks that were interrupted three years ago.

European leaders continued to insist that negotiations would only be meaningful if a ceasefire was established first. Indeed, if the Kremlin intended to reiterate the same maximalist conditions it had presented three years ago – conditions it had also pushed for in negotiations with Trump’s representatives in April, and which Kyiv sees as tantamount to capitulation – then what would be the point of a new round of talks? Putin's aide Ushakov confirmed that Moscow would stand by its original 2022 position.

Zelensky’s initial reaction to Putin’s initiative also suggested that a ceasefire should precede negotiations. ‘We expect Russia to confirm a complete, long-term, and reliable ceasefire starting tomorrow, 12 May, and Ukraine is ready to meet’, he wrote. However, Donald Trump unexpectedly picked up the ball Putin had dropped in a rather ambiguous post: ‘President Putin doesn’t want a ceasefire agreement with Ukraine but instead wants to meet on Thursday in Turkey to negotiate a possible end to the BLOODBATH. Ukraine should agree to this IMMEDIATELY. At the very least, they will determine if a deal is possible, and if not, European leaders and the US will know where things stand and can act accordingly! I’m starting to doubt that Ukraine will make a deal with Putin, who is too busy celebrating World War II victory, which could never have been won (not even close!) without the United States of America. HOLD THE MEETING, NOW!!!’

Thus, Trump simultaneously undermined the ultimatum presented to Putin (making ceasefire a precondition for negotiations) by urging Zelensky to enter direct talks without any conditions, while also expressing scepticism about the ability of Russia and Ukraine to make progress in these talks. Shortly after, Zelensky announced he would wait for Putin in Istanbul on Thursday. A few hours later, Trump said he might also be in Istanbul.

At first glance, Putin’s statement seemed like an asymmetric move – both rejecting the ceasefire ultimatum and proposing continued peace efforts, but on Russia’s terms. Many observers interpreted this as the Kremlin’s attempt to stall for time, by refusing a truce yet not dismissing negotiations outright. Conversely, Zelensky’s announcement that he would personally travel to Istanbul appeared to escalate the situation. Trump’s statement that he, too, might travel there seemed, on the surface, to place Putin in a nearly impossible position.

However, this interpretation is likely incorrect. The key detail is that in his late-night speech, Vladimir Putin was the first to propose a specific date for the resumption of negotiations on Thursday, 15 May. If the intention had been to ‘drag things out,’ specifying an exact date would not have made sense. Especially since it is the only day when Donald Trump would be finishing his visit to Saudi Arabia but had not yet left Eurasia.

In other words, it was Putin himself, fully aware of Trump’s aspirations, who hinted at the possibility of a meeting in Istanbul, during which Trump would have the chance to fulfil his ambitious plan for resolving the Ukraine crisis during his first foreign tour. And Trump seized the opportunity.

Who will lose and what is at stake?

Trump’s arrival in Istanbul for a meeting with Putin and Zelensky only makes sense if, under his patronage, some form of agreement is signed, at the very least, a temporary truce that could be declared a diplomatic victory for the American president. But what will this agreement include? We do not know. It is unclear whether Zelensky and Ukraine’s European partners know either. It is entirely possible that final terms are still being negotiated at this very moment (this is indicated by today's public comments by Steve Whitkoff, a consistent advocate of major concessions to Moscow).

However, we do know who has already agreed to come to Istanbul and who is almost certain not to be there. Zelensky, facing pressure from Washington over the suspension of military aid to Ukraine, was compelled to follow Trump’s directive. Meanwhile, European leaders, those of the UK, France, and Germany, who have backed Zelensky in previous instances of US pressure on him, are almost certainly not attending.

At the same time, Putin has yet to respond to either Zelensky’s willingness to travel to Istanbul or Trump’s hints that he might also be there. Putin’s silence best demonstrates who holds the stronger position: at this moment, it is his decision that will determine whether the meeting takes place. This means he retains the ability to capitalise on Trump’s ambition of signing an agreement during his first foreign tour.

In reality, after two months of negotiations between Trump’s team and the Kremlin, one issue remains the principal sticking point. Seeking a swift diplomatic success, Trump’s administration was willing throughout April to make major concessions to Moscow, including recognising Crimea as Russian territory. However, two demands from the Kremlin emerged as red lines for Kyiv and its European allies: the surrender of territories that Russia has not yet fully occupied but has already declared its own, and a condition that European allies must neither assist Ukraine in strengthening its defence capabilities nor maintain any presence there after the end of hostilities.

Moscow appeared willing to drop the first demand, but the second, which would leave Ukraine defenceless against future Russian aggression, became the barrier that halted negotiations between Moscow and Washington in late April. For Ukraine and Europe, this is not only a matter of Ukraine’s security but also of whether private businesses can be involved in its reconstruction. There is concern that a final agreement, drafted without Zelensky or European input, could include concessions on precisely this issue.

If Putin does not travel to Istanbul, negotiations at the ministerial level will likely yield no outcome. However, if word emerges that Putin is heading to Istanbul, Ukraine and its European partners should treat it as a warning sign. Zelensky will have little room for manoeuvre if Putin and Trump arrive in Istanbul with an agreement that Trump pressures him to sign. That said, over the past three years, Zelensky has repeatedly demonstrated remarkable resilience and tactical ingenuity, driven, perhaps, by sheer desperation.