In early 2013 the reigning Miss Universe, 20-year-old American Olivia Culpo, travelled to Moscow to film a music video with a Russian pop star called Emin Agalarov, the son of a billionaire real estate mogul with ties to President Vladimir Putin.
One thing led to another and, on June 18 that year Donald Trump, then owner of the Miss Universe pageant, announced he would be whisking 86 of the world’s most beautiful women to Moscow to appear at the Crocus City Hall, a 7,500-seat concert venue, owned by Emin’s father.
‘Do you think Putin will be going to The Miss Universe Pageant?’ Trump tweeted later that day. ‘If so, will he become my new best friend?’
Following the American President’s extraordinary remarks yesterday in response to complaints from Ukraine’s President Zelensky that he’d been left out of peace talks between the US and Russia, questions are being asked about the true nature of Trump’s ‘friendship’ with the man in the Kremlin.
‘Today I heard, ‘Oh, well, we weren’t invited.’ Well, you’ve been there for three years… you should have never started it. You could have made a deal,’ said Trump, as if he was unaware that it was Russia that sent a 40-mile long convoy of military vehicles, including 1,000 tanks, across the border into Ukraine in February, 2022. He added that a ‘half-baked negotiator’ could have secured a settlement years ago ‘without the loss of much land’.
Over the years, the maverick New York property magnate has made no secret of his admiration for strongman leaders such as China‘s Xi Jinping and Hungary‘s
Viktor Orban. And the day after the Russian invasion of Ukraine began, Trump described the military move as ‘genius’ and its architect as ‘savvy’.

Questions have been raised over the seemingly cosy relationship between US President Donald Trump and Russia’s Vladimir Putin (pictured in 2019)

Donald Trump is seen here at the Miss Universe contest in 2013
There have even been suggestions that Putin has kompromat – damaging information – on the American President, most notably after a bombshell dossier produced by a former MI6 officer in 2016 alleged that ‘the Russian government was working to get Mr Trump elected’. Trump has long dismissed such allegations as ‘fake news’ but the fog of speculation has only increased in recent months, with the controversial appointment of Putin ‘fan girl’ Tulsi Gabbard as Director of National Intelligence and the sight of Tucker Carlson, the conservative media pundit who conducted a soft-soap interview with the Russian president in Moscow a year ago, visiting Trump at the White House. But the truth is that the American President’s links to the Russian establishment go back decades and his efforts to end the war on terms seemingly friendly to Putin put his decision in a startling new light. In the mid-1990s, Trump’s real estate empire was teetering on the brink of ruin.
Three of his casinos and one of his hotels had filed for bankruptcy and he was considered so toxic commercially that no US bank would do business with him.
‘He could not get anybody in the United States to lend him anything,’ Trump’s former longtime architect, the late Alan Lapidus, said in 2018. ‘It was all coming out of Russia. His involvement with Russia was deeper than he’s acknowledged.’
The money is said to have been advanced by wealthy individuals from Russia and the former Soviet republics, some of them oligarchs close to Putin.
And Trump’s links to such biznismen continued in the years that followed. One of his most significant partners in the early Noughties was the New York-based Bayrock Group, founded by Kazakh property developer Tevfik Arif, who had spent 17 years at the Soviet-era Ministry Of Commerce And Trade in Moscow. One of Arif’s senior advisers at this point was one Felix Sater, the son of a Russian mafioso, who was once convicted of running a protection racket.
It soon became clear that the apple hadn’t fallen far from the tree. In 1991, Sater got into an argument over a girl with another man in a Manhattan restaurant.
He stabbed his victim in the cheek and neck with the stem of a cocktail glass, breaking his jaw, lacerating his face and severing nerves. The wound was so serious it required 110 stitches.
Sater was subsequently convicted of first degree assault and spent 15 months in prison.

Firemen extinguish a fire inside a residential building that was hit by a missile on February 25, 2022 in Kyiv, Ukraine

People cross a destroyed bridge as they evacuate the city of Irpin, northwest of Kyiv, during heavy shelling on March 5, 2022 The city was overrun by Russian forces in the early days of the war, and would be occupied for a month. The images of people – the young and the old – being helped across the wrecked bridge became emblematic of the human cost of the war

Ukrainian soldiers take positions outside a military facility as two cars burn, in a street in Kyiv, Ukraine, February 26, 2022. Russian troops stormed toward Ukraine’s capital that weekend and street fighting broke out as city officials urged residents to take shelter
Seven years later, Sater was involved in a rather more heavyweight crime, pleading guilty to his involvement in a $40 million stock fraud scheme orchestrated by the Russian Mafia.
This is the man who became a senior adviser to Trump when the construction of Trump SoHo, a $450 million, 46-storey hotel condominium, got underway in New York in 2006.
In 2008, Trump’s eldest son, Donald Trump Jr, brazenly admitted the scale of the family business’s dependence on Russian cash.
‘Russians make up a pretty disproportionate cross-section of a lot of our assets,’ he admitted. ‘We see a lot of money pouring in from Russia.’
But it wasn’t one-way traffic. As well as accepting finance from the land of the tsars, Trump had long been keen to build an outpost in Moscow. In his bestselling business advice manual The Art Of The Deal, published in 1987, Trump wrote that he had talked with Russia’s then ambassador to Washington, Yuri Dubinin, about the possibility of ‘building a large luxury hotel, across the street from the Kremlin, in partnership with the Soviet government’.
While that joint venture ultimately fell through, the tycoon’s interest in a Trump Tower in the Russian capital was sparked anew after the collapse of the USSR.
It was the Moscow-born Sater who identified a site for a Trump skyscraper and, while plans for the project were dogged by delays, Trump was optimistic enough after holding 2013’s Miss Universe pageant in Russia, to tweet: ‘TRUMP TOWER-MOSCOW is next.’
By 2015, a New York architect had completed plans for what would have been the tallest skyscraper in Europe, a glass obelisk 100 storeys high, with the Trump logo on multiple sides. In an email to Trump’s lawyer later that year, Sater boasted: ‘Buddy, our boy can become president of the USA and we can engineer it. I will get all of Putins [sic] team to buy in on this. I will manage this process.’

Dominic Midgley (pictured) writes about the curious relationship between Trump and Putin
It was only in June 2016, with a presidential election looming, that Trump appears to have dropped the idea once and for all.
Within months, however, he was reeling from the devastating findings of a dossier produced by ex-MI6 officer Christopher Steele.
Having spent 20 years working on Russia-related issues for British intelligence, Steele was so concerned that Trump might be being blackmailed by Russia that, in July 2016, he passed on his findings to the FBI – and six months later its astonishing findings were published by news website Buzzfeed.
While Steele’s dossier alleged ‘that the Russian government was working to get Mr Trump elected’, that Russia sought ‘to cultivate people in Trump’s orbit’ and that many of his campaign officials and associates had numerous secretive contacts with Russian officials and agents, it also contained a more scurrilous suggestion.
To keep their asset in line, Steele alleged, the Russian security services had videotaped Trump hiring and watching prostitutes ‘perform a ‘golden showers’ [urination] show’ in a Moscow Ritz-Carlton hotel room in 2013, the year the Miss Universe pageant was held in Russia.
But according to a book by the Harvard-educated American journalist Craig Unger, called American Kompromat: How The KGB Cultivated Donald Trump, published in 2021, the Russians’ wooing of Trump first started almost 50 years ago.
One of Unger’s sources was a former KGB major called Yuri Shvets, who was posted to Washington DC in the 1980s as a US correspondent for the Russian state news agency TASS.
The way Shvets tells it, Trump was identified as a promising contact as early as 1977 when the up-and-coming young businessman married his first wife, Ivana Zelnickova, a Czech model.
When Trump opened his first big property development, the Grand Hyatt New York hotel near Grand Central station three years later in 1980, he bought 200 television sets from Semyon Kislin, a Soviet emigre who co-owned Joy-Lud Electronics on Fifth Avenue.
According to Shvets, Joy-Lud was controlled by the KGB and it was Kislin, a so-called ‘spotter agent’, who identified Trump as a potential asset. (It should be said Kislin denies that he had a relationship with the KGB.) ‘For the KGB, it was a charm offensive,’ Shvets told The Guardian in 2021. ‘They had collected a lot of information on [Trump’s] personality so they knew who he was personally.
‘The feeling was that he was extremely vulnerable intellectually and psychologically, and he was prone to flattery.
‘This is what they exploited. They played the game as if they were immensely impressed by his personality and believed this is the guy who should be the President of the United States one day: it is people like him who could change the world… so it was a big achievement for the KGB active measures at the time.’

Russian President Vladimir Putin is seen on a screen set at the Red Square as he addresses a rally and a concert marking the annexation of four regions of Ukraine Russian troops occupy – Lugansk, Donetsk, Kherson and Zaporizhzhia, in central Moscow on September 30, 2022
As Unger wrote in his book: ‘Putin will be thrilled to have Trump as a negotiating partner. He’s an easy mark, a narcissist. The key is to flatter him. He looks up to Putin.’
After forging a relationship with the Russian President during his first term in the White House from 2017 to 2021, Trump had as many as seven private phone calls with Putin after leaving office and secretly sent him COVID-19 test machines during the height of the pandemic, according to the highly respected Watergate reporter Bob Woodward in his book, War, published late last year.
On one occasion in early 2024, Woodward reports that Trump asked an aide to leave his office at his Florida resort, Mar-a-Lago, so that the former President could have a call with Putin in private.
There have been three major probes into Trump’s Russian links in recent years: an FBI special counsel investigation, the Mueller probe into Russian interference in the 2016 presidential election and a Senate Intelligence Committee report on the same topic.
While all three uncovered highly controversial relationships between Trump’s camp and the Russians, none of them produced a smoking gun.
But doubts remain over where Trump’s loyalties really lie thanks, in part, to the controversial nature of some of his Cabinet picks and close associates.
Take Tulsi Gabbard, his choice as Director of National Intelligence. Her frequent echoing of Kremlin talking points has earned her praise in Russian state media.
Indeed, late last year Russian state-owned news agency RIA Novosti went so far as to call Gabbard a ‘superwoman’, claiming that Ukrainian intelligence views her as ‘probably an agent of the Russian special services’.
When the controversy over his Russian links reached fever pitch in 2019, Trump sought to lampoon what he saw as his critics’ obsessiveness by sarcastically parroting: ‘Russia, Russia, Russia.’
But when he makes appointments such as Gabbard, it’s no wonder that speculation over The Donald’s true motivations persist to this day.
- Dominic Midgley is author of Abramovich: The Billionaire From Nowhere, a biography of the Russian oligarch who once owned Chelsea FC.