Sitting in a makeshift studio overlooking the Moscow river on a crisp day in November 2013, Donald Trump pouted, stared down the lens of a television camera and said something he would come to regret.

Asked by an interviewer whether he had a relationship with Russian president Vladimir Putin, the brash New York businessman could not resist boasting. “I do have a relationship with him,” Trump said.

Russia’s strongman had “done a very brilliant job”, Trump told MSNBC’s Thomas Roberts, before declaring that Putin had bested Barack Obama. “He’s done an amazing job – he’s put himself really at the forefront of the world as a leader in a short period of time.”

Trump, a teetotaler, seemed intoxicated by the buzz surrounding the glitzy event that had brought him back to Moscow: that year’s instalment of the Miss Universe contest that he then owned.

Four years later, he is struggling to shake off the hangover.

The 2013 pageant has become a focal point for the simultaneous investigations, led by special counsel Robert Mueller and congressional committees, into whether associates of Trump colluded with Russian officials to help them win the 2016 US presidential election.

Investigators are examining closely efforts apparently made by the Russian government to pass Trump’s team damaging information on Hillary Clinton, using Trump’s politically connected Miss Universe business partners as couriers.

They are also looking into the $20m fee that Trump collected for putting on the pageant from those same business partners – along with extraordinary allegations about Trump’s private conduct behind closed doors at the Ritz-Carlton hotel during his 2013 stay in Moscow.

The Russians have a history of using investments to gain leverage over influential people and later calling in favours Al Franken

The Guardian has learned of additional, previously unreported, connections between Trump’s business partners on the pageant and Russia’s government. The ties are likely to attract further scrutiny by investigators who are already biting at the heels of Trump associates.

A full accounting of Trump’s actions in the Russian capital as that autumn turned to winter may be critical to resolving a controversy that has already consumed the first eight months of his presidency.

“Our committee’s investigation will not be complete unless we fully understand who President Trump met with when he was over in Russia for Miss Universe, and what follow-up contacts occurred,” Eric Swalwell, a California Democrat on the House intelligence committee, said in an interview.

Trump’s attorney, John Dowd, declined to answer when asked whether the president’s team accepts that the Miss Universe contest is a legitimate area of inquiry for investigators. “Fake news,” Dowd said in an email.

Emin Agalarov, Donald Trump and Aras Agalarov attend the Miss Universe pageant on 9 November 2013 in Moscow, Russia. Photograph: Victor Boyko/Getty Images

‘Look who’s come to see me!’

It was a whirlwind courtship.

Trump was instantly taken with Aras Agalarov, the billionaire owner of the Crocus Group corporation, when the two wealthy property developers met for the first time on the fringe of the Miss USA contest in Las Vegas in mid-June 2013.

After just ten minutes of discussion, Trump was showing off his new friend. “He clapped me on the shoulder, gave a thumbs up, and started shouting, ‘Look who’s come to see me! It’s the richest man in Russia!’,” Agalarov recalled to a Russian magazine later that year, before clarifying that his fortune – estimated at about $2bn – was far from Russia’s biggest.

The meeting had been set in motion only a month earlier, when Agalarov’s son Emin, a pop singer who is well-known in eastern Europe, filmed his latest music video in Los Angeles. His co-star was the reigning Miss Universe, a casting choice that brought the Agalarovs into contact with Trump’s beauty pageant division.

The idea of hosting that year’s contest in Russia was raised over dinner by Paula Shugart, Trump’s top Miss Universe executive, according to Emin Agalarov. In a little-noticed interview published in July, Emin said Trump’s organisation seemed to be in need of the money that Moscow could offer. “We have a lot of debts,” he quoted Shugart as saying. Miss Universe denies that Shugart said this.

In any case, a price tag of $20m to be paid by Agalarov in return for Trump bringing the Miss Universe contest to Russia was quickly agreed upon. Several Democrats have raised concerns that the payment – like the billions in bank loans he secured to bring himself back from the brink in the early 1990s – may have left Trump indebted to foreign influences.

“The pageant was financed by a Russian billionaire who is close to Putin,” Senator Al Franken of Minnesota told a congressional hearing in May. “The Russians have a history of using financial investments to gain leverage over influential people and then later calling in favours. We know that.”

Just four weeks after Emin’s video shoot, at the backslapping Las Vegas get-together, Trump announced that the deal was done. Miss Universe would be held at the Agalarov family’s sprawling Crocus City complex on the edge of Moscow, described by Trump as ”Russia’s most premier venue”.

Emin Agalarov, Miss Universe 2013 winner Gabriela Isler and Donald Trump. Photograph: Kommersant Photo/Kommersant via Getty Images

In a dreary Vegas hotel banqueting hall, the beaming new business partners ate a celebratory dinner together. Video footage later obtained by CNN showed Trump at his most oleaginous. “What a beautiful mother you have,” he told Emin. The principals were joined by an assortment of hangers-on including Emin’s publicist – a portly Briton named Rob Goldstone.

It was Goldstone who would contact Trump’s son Donald Jr during the 2016 presidential campaign with a sensitive message, revealed in emails released last month. The “crown prosecutor of Russia” – assumed to be Goldstone’s garbled billing for Yury Chaika, the Russian prosecutor general – wanted the Trump campaign to have some documents that would “incriminate Hillary”, he said. And the Agalarovs would deliver them.

“This is obviously very high level and sensitive information but is part of Russia and its government’s support for Mr Trump – helped along by Aras and Emin,” Goldstone wrote. Rather than express surprise or question the apparent Kremlin operation Goldstone was describing, Donald Jr pressed ahead and arranged the meeting. “If it’s what you say I love it,” he replied.

Rob Goldstone. Photograph: Stringer/Reuters

Aras Agalarov made a suitable sherpa. While not a member of Putin’s inner circle, Agalarov cultivated friendly relations with the Kremlin while rising to the country’s oligarch class with a profitable network of shopping malls. He travelled around in a $44m Gulfstream private jet.

Less than two weeks before the Miss Universe finals, Putin awarded Agalarov the prestigious Order of Honor medal, after Crocus had completed for him a billion-dollar transformation of a former military base into a new state university.

“I wish to thank you so much for your work and contribution to the development of this country,” Putin told Agalarov and his fellow honorees. Crocus would go on to be further rewarded with more government construction contracts, including for stadiums that are to be used for next year’s soccer World Cup tournament in Russia.

Irakly ‘Ike’ Kaveladze. Photograph: Twitter

Separately, one of Agalarov’s top executives, Irakly “Ike” Kaveladze, also has his own relationships with several influential Russians. Kaveladze, a publicity-shy Crocus vice president, was the so-called “eighth man” at the 2016 Trump Tower meeting where Donald Jr hoped to receive dirt on Clinton.

While relatively unknown to the public before news of the meeting emerged in July, Kaveladze has in fact been an associate of some of Russia’s richest and most powerful people for the past three decades.

The Guardian has established that Kaveladze was involved in the $341m takeover of a US company by a Russian mining firm belonging to an associate of Putin, and was a business partner to two former senior officials at Russia’s central bank.

In 2003, the Colorado-based firm Stillwater Mining was bought by Norilsk Nickel, a metals corporation in Moscow led by Vladimir Potanin, one of Russia’s wealthiest oligarchs, who is so favoured by Putin that he has played on the president’s “Hockey Legends” ice hockey team .

Vladimir Potanin. Photograph: Bloomberg/Bloomberg via Getty Images

As part of its $341m purchase of the American firm, Norilsk nominated Kaveladze to be one of its five handpicked directors on Stillwater’s new board, according to a filing by the company to the US Securities and Exchange Commission (SEC). Kaveladze was billed as the president of “an international consulting boutique” serving a “US and Eastern European clientele”.

The deal was the first time a Russian company had ever taken a majority stake in a publicly traded US company. It was viewed as critical by the Kremlin. Putin was reported at the time to have personally advocated for the deal’s approval by US regulators during a meeting with then president George W Bush earlier in 2003.

Norilsk was then co-owned by Potanin and Mikhail Prokhorov, another major Russian oligarch, who later sold his stake. Prokhorov, who has had mixed relations with the Kremlin, now owns the Brooklyn Nets basketball team in New York. Kaveladze and Prokhorov had been classmates at the Moscow Finance Institute in the late 1980s and formed a partnership selling customised jeans between their studies.

Kaveladze’s ascent to the Stillwater board was eventually derailed, according to a source, after the discovery of his earlier involvement in a $1.4bn California-based scheme involving shell companies and transfers from Russia, which US authorities said may have been used for money laundering. Norilsk said he withdrew from the process for personal reasons.

The Guardian previously revealed that Kaveladze’s partner in that operation was Boris Goldstein, a Soviet-born banker whose ties to former KGB officers attracted interest from US investigators after he moved to California in the early 1990s. In a remarkable coincidence, the US attorney in San Francisco whose office eventually declined to bring criminal charges over their alleged money-laundering scheme was Robert Mueller, the special counsel now looking into Kaveladze’s reappearance.

Also previously unreported is Kaveladze’s close friendship with Andrei Kozlov, who was first deputy chairman of Russia’s central bank under Putin for four years before being assassinated in 2006 as he attempted to clean up Russia’s corrupt banking system.

Andrei Kozlov. Photograph: Alexei Sazonov/AP

At the turn of the 1990s, Kaveladze and Kozlov had gone into business together after graduating from the Moscow Finance Institute. They founded a small publisher and translator of financial books with Dmitry Budakov, another classmate, who also went on to be a senior executive at Russia’s central bank before running a division of the state-owned Bank of Moscow.

The young entrepreneurs capitalised on a hunger for financial literature among players in Russia’s rapidly privatising economy, pricing their textbooks at around $250. One book was published in Kaveladze’s name. His 1993 work, Protecting trade secrets in the US: A guide to protecting your business information, remains available in several university libraries.

Do you think Putin will be going to The Miss Universe Pageant ... if so, will he become my new best friend? Trump in 2013

According to an official history of that time, their book publishing outfit, ECO-Consulting, was established as a division of Crocus International, Aras Agalarov’s then-burgeoning business empire. In return for the security of being part of a larger corporation, Kaveladze and his business partners advised Agalarov on economic and financial affairs, according to a memoir of the time by Budakov. “Cooperation was mutually profitable,” he wrote.

Kaveladze soon moved to the US, landing first in Pennsylvania. He had earlier spent almost a month visiting the Gettysburg area after graduating in 1989. As a tribute to their departed guest, locals held a “Perestroika” 5,000-metre running race near the site of the civil war battlefield as part of their Labor Day celebrations, according to the Gettysburg Times.

When Kaveladze moved to the US, he became close with a middle-aged couple in York, Pennsylvania. Judith Shaw, whose obituary affectionately named Kaveladze as her “adopted son”, died in February 1993; her widower did not respond to requests for comment. Kaveladze eventually bought an apartment in New York.

More than 25 years after their first venture, Kaveladze continues to work alongside Agalarov at Crocus. Their company has become one of the biggest corporations in Russia, carrying out government building contracts worth hundreds of millions of dollars from Putin’s administration – and sealing international deals with tycoons such as Trump.

An attorney for Kaveladze did not respond to requests for comment prior to publication. After this article was first published, an attorney for Kaveladze contacted us to say that Kaveladze considers a number of matters in the article to be inaccurate. In particular Kaveladze denies being business partners with either Prokhorov or Goldstein. In relation to Prokhorov, Kaveladze says that he only worked for his jeans business for two days whilst studying at the Moscow Finance Institute. In relation to Goldstein, he says he has only met him briefly on two occasions. Kaveladze also denies being involved in the takeover of Stillwater Mining by Norilsk Nickel.

Contestants pose at the Miss Universe pageant on 9 November 2013 in Moscow. Photograph: Victor Boyko/Getty Images

‘Will he become my new best friend?’

Before leaving the US for his big Russian show in 2013, Trump made an unusual public appeal.

“Do you think Putin will be going to The Miss Universe Pageant in November in Moscow,” he asked on Twitter, and “if so, will he become my new best friend?” A source in Moscow told the Guardian that a meeting with Trump was indeed pencilled into Putin’s diary by aides, but fell off his schedule a few days beforehand.

Agalarov later said that Putin sent his apologies to Trump in the form of a handwritten note and a gift of a traditional decorative lacquered box. It is not known whether Trump met any associates of Putin in lieu of the president himself, but he certainly claimed to have.

“I was with the top-level people, both oligarchs and generals, and top-of-the-government people,” he said in a radio interview in 2015. “I can’t go further than that, but I will tell you that I met the top people, and the relationship was extraordinary.”

Having flown from the US overnight, Trump arrived in Moscow on 8 November and checked in to the Ritz Carlton hotel. It was a choice that has since become notorious. An opposition research dossier compiled for a private client by a former British spy, which was later published by BuzzFeed News, alleged that the Kremlin held compromising and lurid footage of Trump and a pair of prostitutes during his stay at the hotel.

Elsewhere in the dossier, author Christopher Steele wrote that two sources alleged Trump also had illicit sexual encounters in the Russian city of St Petersburg during a separate visit to the country. The sources, according to Steele, said that Aras Agalarov would “know the details”. Trump denies any wrongdoing.

[Putin]'s probably very interested in what you and I are saying ... and I’m sure he’s going to be seeing it in some form Trump to MSNBC in 2013

It is plausible – but unproven – that attempts were made to surveil Trump during his trip.

“If you are in their field of interest then the FSB will absolutely attempt to carry out surveillance,” said a Russian hotel industry source, who did not want the name of his hotel mentioned due to the sensitivity of the topic.

The source said there was little that hotel managers could do about FSB demands, and that they are sometimes forced to provide access to rooms for agents. “In the bigger hotels you also definitely have a number of people on the staff who work on the side for the FSB, so they would have had absolutely no problem getting into the room if necessary.”

Putin said earlier this year that it was absurd to think the FSB would have bugged or secretly filmed Trump’s room in 2013, as he was not even a politician at that point. Russia did not simply bug every American billionaire who visited the country, according to the president.

But the hotel industry source cast doubt on that claim. “Surveillance doesn’t happen that often, but I’m pretty sure Trump would have been of a sufficient level to warrant it,” said the source. “I’ve seen people of lower levels than him watched for sure.”

When the late-night talkshow host Stephen Colbert managed in July to gain access to the Ritz-Carlton’s presidential suite, where Trump is said to have stayed, an unexplained power cable was discovered dangling from a section of the bedroom wall that was hidden behind a non-illuminated mirror.

Whatever the truth about how closely Trump was being monitored by the Kremlin, a remark he made about Putin during that boast-filled interview with MSNBC seems particularly curious with the benefit of hindsight.

“I can tell you that he’s very interested in what we’re doing here today,” Trump said of the Russian president. “He’s probably very interested in what you and I are saying today – and I’m sure he’s going to be seeing it in some form.”

Some elements of Steele’s dossier have reportedly been confirmed by investigators, but other details have been shown to be false. And Trump has been backed up on the claims about his private conduct by Emin Agalarov. “While the world tries to figure out what Donald Trump was doing in a hotel in Moscow during Miss Universe – I actually know because he was filming my music video,” he wrote on Instagram.

Early in the morning of 9 November, Trump was taking part in filming at the hotel for the video of Emin’s single In Another Life. The video features Emin dreaming about being surrounded by bikini-clad Miss Universe contestants, before waking up to be lectured by Trump and told: “You’re fired.”

Yulya Alferova, a businesswoman and blogger who was hired by Crocus Group to help with their social media presence at that time, arrived at the hotel that morning and met Trump shortly after the filming had finished. After a brief conversation, Trump took a shine to her, and Emin invited her to join a small group for lunch.

“We talked about Twitter, and I asked him if he agreed that Twitter is the strongest and sometimes the most dangerous social media. He asked me about real estate, because I told him it’s one of my professional interests,” said Alferova, who once achieved notoriety in Russia for posting a photograph of her cat eating black caviar.

Later, Trump told her that she should contact him if she was ever in New York. He had his assistant hand her a business card. But there was nothing inappropriate about his conduct, Alferova said, describing Trump as a “gentleman” who always acted “correctly and properly” in their interactions.

The pageant went off without a hitch. Gabriela Isler of Venezuela was crowned the winner. An after-party was held for the contestants and friends of the organisers. There were three private boxes: one for the Agalarovs, one for Trump and one for Roustam Tariko, the chief of Russian Standard, the Russian vodka company and bank, which sponsored Miss Russia. The American band Panic! At The Disco provided the music, and contestants mingled with guests. Several were invited into the boxes to speak with Trump and the oligarchs. Aerosmith singer Steven Tyler, who had performed at the ceremony, was also there.

“Trump was still there when I left at 2am,” a guest at the party told the Guardian. “There were a lot of people there, it was fun but pretty civilised.” Alferova, the businesswoman and blogger, remembered multiple guests approaching Trump and asking for photographs with him.

“There were no government people present and no major Forbes List people except Aras [Agalarov] and Roustam [Tariko]” said one of the organisers of the event, suggesting Trump’s boastful claims that “all the oligarchs” attended may have been false.

Still, during his Moscow stay Trump also attended a private meeting with leading Russian businessmen at Nobu, the high-end Japanese restaurant chain for which Agalarov owns the Moscow franchise. The dinner was arranged by Herman Gref, Putin’s former energy minister and now chief executive of the state-owned Sberbank, Russia’s biggest bank. The bank, which was another sponsor of Miss Universe, was later among the Russian companies sanctioned by the US over Russia’s annexing part of Ukraine in 2014.

“He’s a sensible person, very lively in his responses, with a positive energy and a good attitude toward Russia,” Gref told Bloomberg.

Agalarov has said he and Trump also met with the businessmen Alex Sapir and Rotem Rosen – Trump’s old partners on the controversial Trump Soho project in New York – to discuss opportunities in Moscow. Agalarov later said they struck an agreement in principle to go ahead. Trump seemed to think so: “TRUMP TOWER-MOSCOW is next,” he said in a thank you note to Agalarov on Twitter. Eight days later, Sberbank announced it was lending Agalarov 55bn roubles ($1.3bn) to finance new projects in Moscow.

Trump Tower Moscow, like so many other Russian twinkles in Trump’s eye over the past three decades, did not materialise. But it recently emerged that the conversations continued behind the scenes even after he began his long-threatened campaign for president.

In October 2015, four months into his campaign, Trump signed a “letter of intent” to build a tower in Moscow. Pulling the strings on the abortive deal was Felix Sater, yet another Russian business associate of Trump, who once served time in prison for stabbing a man in the face with a broken cocktail glass.

“I will get Putin on this program and we will get Donald elected,” Sater reportedly told Trump’s attorney in an email. “Buddy our boy can become President of the USA and we can engineer it … I will get all of Putins team to buy in on this.”

The future of Trump’s presidency may rest on what else was said and done relating to the project – and whether investigators who already smell blood can prove it.

On at least three occasions following the Miss Universe trip, Trump had publicly claimed to have met Putin. But when asked by reporters at a campaign stop in Florida in July 2016 to clarify the status of his relationship with the Russian president, as concerns over Russian election interference mounted, Trump gave a rather different version.

“I never met Putin,” said Trump. “I don’t know who Putin is.”