Trump’s long-standing infatuation with Putin is about to meet its ultimate test

One hundred days of the second Trump era dawns amid vast uncertainty about the status of the President’s pledge to bring three years of devastating war in Ukraine to an end. A bullish new President promised to stop the fray “within 24 hours” on taking office. Even allowing for Trumpian hyperbole, that looks threadbare three months on as the fighting continues, battering Ukraine’s army, targeting civilians and destroying vital infrastructure.

For a US leader with an imperturbable belief in his deal-making prowess, the prospect of playing peacemaker and a chance to restore a closer bi-lateral relationship between Moscow and the US to the centre of his presidency has both personal and political allure.

But despite a mighty push to get a deal done by his milestone in office, there is no victory sign so far for a President who has pulled out all the stops in an intense period of shuttle diplomacy. The only Kremlin offer has been a single day of hostility cessation at Easter (to appease the Orthodox Church) and now a three-day ceasefire promised from the 8 May holiday, when Russians mark the end of the Second World War with patriotic fervour.

The quest for a truce has thrown the relationship between the two dominant leaders on the world stage into stark relief. The Putin and Trump interplay is also a contest for the upper hand – or as Lenin neatly put it of such things, “kto kovo” (who gets the better of whom?).

The terms of the duo’s dealings remain mysterious. The two have only ever met five times and their personal conversations are largely undocumented. Trump has ditched the diplomatic protocols of “memcoms” – memorandums taken at high level bilateral meetings to avoid misunderstandings or resulting commitments disputed later.

The one figure the President has come to trust to carry out his (often changeable) wishes towards Moscow is a fellow business investor, Steve Witkoff, who has been dispatched repeatedly to Saudi Arabia and Moscow to get the deal done.

His opposite number Kirill Dmitriev is head of the Russian sovereign wealth fund – a murky entity. Dmitriev, who has Ukrainian parentage studied in the US after the fall of communism and worked for Goldman Sachs, but is also a prominent fixture on the US sanctions list. One strong motivator for Putin to move on Ukraine is the hope of loosening sanctions which are hitting a Russian economy distorted by vast spending on defence and the war.

As progress has stalled, Trump has pivoted from tactics which were essentially focused on dealings with Putin to the exclusion of Ukraine’s Volodmyr Zelensky to a triangular dynamic. Having dressed down a frustrated Ukrainian leader at a White House encounter that ended in a fractious row a few weeks ago, Trump has shunted blame for the war and failure to make peace between the two countries.

He has lambasted Zelensky for standing up to Moscow’s aggression – “you never should have started it” – and pulled back from US military and financial support, while imposing a deal on US access to critical resources.

In the past couple of weeks, however, Trump’s patience with Putin’s equivocations has worn thin. Meeting Zelensky at the Pope’s funeral at the weekend, the ambience was amicable, even supporting Zelensky’s determination to protect his country and it was Moscow that got a scolding for continuing air strikes on Ukraine as “very bad timing”.

Key differences between Trump and Putin

For all of this activity and signalling, the outcome is opaque. “We have the confines of a deal, I believe,” Trump told reporters on Sunday, saying he wanted Russian President Vladimir Putin to “sign it and be done with it and just go back to life.”

Having covered the Kremlin and wars on the Russian periphery since the 90s and the rise of the Russian leader to prominence and the embrace of a Soviet doctrine, amped up by a personal determination to eliminate Ukraine’s independence and military capacity and use the opportunity to push back Nato in Eastern Europe, I would say going “back to life,” in any durable sense of a lasting peace is improbable.

At the same time, both sides are exhausted by the war. Ukraine has lost around 70,000 men and civilian victims of a war that includes horrors such as chemical weapons and the use of cluster munitions. Russia, on credible estimates, has lost well over 100,000 combatants as well as being subject to an increasing number of car bomb attacks masterminded by Ukrainian special operations on senior military figures, reminding domestic opinion that the conflict does not end at Ukraine’s border.

Much depends then on the interplay of two men who see themselves as the centre of a particular worldview – and allies or enemies as secondary. I have met both briefly and in Trump’s case, had a short conversation on the eve of his 2016 election win.

In personal terms, they could hardly differ more: Trump, while maverick in mood and oscillation between blunt cheeriness and threatening bluster, loves being around others – “Look after these good people” was his instruction to his minders after my producer and I had managed to wangle too many questions inside a cordon at a rally in Washington.

Putin keeps his distance from visitors and especially westerners. Outside formal occasions, he also retains the old Soviet leaders’ reluctance to meet ordinary Russians and is believed to use body doubles and manipulated social media to appear to do so a lot more than he does. Trump is large, noisy and aften rambling. Small, neat and judo trained, Putin rattles off talking points and digs at foes in rapid-fire Russian.

Some commonality is striking – both have a pronounced anxiety about hygiene and do not like to shake hands. A visitor to Trump’s Florida Mar-a-Lago residence tells me that the swimming pool has a prominent sign warning guests not to enter if they have stomach upsets, whereas Putin in the Covid lockdown was reputed to have had showers dispensing disinfectant installed, which officials has to use before visiting him – and began his habit of entertaining guests at excessively long tables.

The man captured by sly social media taggers in Russia wearing a succession of the world’s most expensive watches was brought up in hardscrabble circumstances of beatings and poverty. That changed fast in the time I covered Putin’s rise from KGB mid-ranker to power in Moscow.

At one point in the 90s, he met a consultant setting up the McKinsey consultancy in Russia and was fascinated by the man’s stylish new backpack – and expressed surprise that it was possible to combine a briefcase design within a rucksack. He has an intelligence officer’s memory for detail: years later when the consultant was in a long receiving line to meet him, by then as President, he stopped and asked,” Where’s the backpack?”

Flattering to keep hold of the Crimea

Today, an appetite for far greater luxury is shared with his US equivalent: Trump’s Mar-a-Lago Florida complex is a palace of gilded furnishings and lavish facilities. The Russian leader’s retreat is dubbed “Putin’s palace,” a vast luxury complex on the Black Sea, closed to outsiders, where he lives with his partner who is rarely seen in public, the ex-gymnast Alina Kabaeva and their two sons, aged around 10 and six. Their affinity is a mixture of strongman attraction – and for Trump, payback for the “Russia hoax” – opponents’ accusations of Russian interference in the 2016 election which brought him to power.

“Let me tell you, Putin went through a hell of a lot with me,” he has said of that period. “He went through a phoney witch hunt where they used him and Russia… Russia, Russia, Russia… The whole thing was a scam, and he [Putin] had to put up with that.”

As the former head of MI6 Alex Younger puts it, Putin has “only one plan which is to flatter Trump into giving him what he wants.” That means an end to the fighting which established Russia as in de facto control of the strategically vital Crimea peninsula – and gives it sway in which parts of occupied territory are kept or handed back and on what terms.

Putin’s wider abysmal record on human rights cannot be unknown to Trump, who has, I am told by one former official “a fascination, bordering on an obsession” with the huge personal file on the Russian leader drawn up by White House security staffers.

The Kremlin boss has jailed, exiled, blackmailed and silenced those who challenge him, presiding over an unnatural rate of people who went out of favour for political or business reasons, falling out of high windows shortly afterwards.

Alas, the days of the US seeking to protect the frayed rights of political opponents – a core element of US Russia policy since the Helsinki Accords of the late 70s allowed many dissidents the right to leave the USSR – has disappeared. In its place is purely transactional dealing – with Ukraine in the middle of a deal aimed at building leverage with Moscow for the US to use against China and Iran.

Trump’s interest in Russia and its potential has long roots. When he helped take the Miss Universe pageant there in 2013, Trump coquettishly commented that he hoped Putin would “become my best friend”. Lurid but unsubstantiated accounts have done the rounds on whether he had a sexual encounter there which was being used as kompromat. That, like many stories of Putin being some form of KGB asset is a hardy perennial among conspiracy theories as to why Trump is keen on closening ties in the former Soviet capital.

The ex-Moscow correspondent Luke Harding’s book Collusion – How Russia helped Trump Win the White House, records Trump’s fascination at meeting the veteran Soviet ambassador Yuri Dubinin in 1986, after he had built Trump Tower. “One thing led to another,” Trump wrote afterwards, “and now I’m talking about building a luxury hotel, across the street from the Kremlin, in partnership with the Soviet government.” The ambassador’s daughter, part of the official Soviet UN delegation rife with KGB spies, subsequently boasted of being persuasive in getting Trump to visit Moscow.

One recent MI6 figure formerly monitoring Russia believes it is “perfectly possible or even probable that the KGB saw in Trump a ‘person of interest’ to be cultivated and to monitor” as a result of this and subsequent encounters. “But that is a different and much wider group from being an active recruit.”

For one thing, being an agent is a time-sucking commitment with rigid ways of operating, which do not fit well with Trump’s freewheeling tendencies and spontaneity. Signing himself into an intelligence relationship with Moscow would have been huge risk for an ambitious American entrepreneur with an eye on politics.

He is rash – but not foolish when it comes to protecting himself. Yet he assists Moscow’s agenda by adopting many of its favoured talking points and bugbears – including the thesis that Nato “expansion” is to blame for endangering Russia’s security. Crucially, he has moved close to accepting the Putin argument that Moscow enjoys a “sphere of interest” beyond its borders and can therefore justifiably curtail freedoms and limit its neighbour’s autonomy.

That brings us back to the determination to forge a deal – as fast as Russia will agree to it and Ukraine can be persuaded to give up any realistic claim to Crimea and sign terms to cauterise the conflict, while it rearms, rests its troops and seeks to shore up its future security with help from a shaken Europe.

Shortly after the Maga President marks his 100th day in office, his Russian counterpart will celebrate a holiday which harks back to an era of Stalin’s wartime rule – and sweeping oppression of Ukraine’s struggle for nationhood. The country’s name literally means “on the edge” – of Russia’s historic empires and Europe. That status has often brought Ukraine war and enmity from Moscow.

Whatever the “art of the deal” finally brewed up between the White House and the Kremlin and an antiseptic handshake, don’t bank on that changing.

• Anne McElvoy is a former Moscow correspondent for The Times and now executive editor at Politico