It’s an enigma at the heart of Nigel Farage’s general election campaign: why has a 30-year-old businessman, self-confessed high-stakes gambler and convicted fraudster flown in from a glamorous Balkan resort to act as his unpaid aide?

George Cottrell was at Farage’s side when the Reform UK leader was , and on a private helicopter flight with him from Ashfield in Nottinghamshire to London. Cottrell was there at a London hotel, ear glued to his phone, as Farage hosted a press conference. He also pitched up in Merthyr Tydfil for the party’s manifesto launch in Wales.

Reform says Cottrell is just one of many party volunteers on the campaign trail, but his extravagant lifestyle and past controversies raise some awkward questions for Farage.

Those who have followed the election campaign in Clacton, the Essex coastal town where Farage is , describe Cottrell as integral to the operation – frequently physically close to the leader and his two-man security detail, as shown in of the core group leaving a campaign headquarters.

One photograph from earlier in the campaign shows Cottrell in a beer garden in Clacton with Farage. Both men are in similar poses: smoking and on the phone, a few yards apart.

The British locations are a far cry from Cottrell’s usual lifestyle. He is said to drive a £300,000 Lamborghini, stay in an £8m townhouse when in London and to have taken Westminster friends including Farage out to his home in Montenegro by private plane from London’s Biggin Hill airport.

Cottrell, who was born in Britain, moved to the tiny Balkan country some time after 2017 when he was convicted in the US and then spent eight months in an American jail after being accused of offering money-laundering services on the dark web. He served time for a single count of wire fraud after 20 other charges were dropped as part of a plea deal.

He is now a familiar figure in the luxurious coastal resort of Porto Montenegro, where he mostly lives, with its gleaming marina a haven for the super-rich with shiny mega-yachts, upmarket restaurants and designer shops such as Dior and Rolex.

Sources told the Guardian he had entertained friends at a villa during trips to the country, with one particular bedroom favoured by Farage, although he reportedly owns a more modest apartment at the five-star Regent Porto Montenegro hotel.

Cottrell’s time in Montenegro has not been without controversy. Last month, he reportedly lost €20m (£16m) in a single poker game, which sparked a public row with his former girlfriend Andjela Vukadinovic, the reigning Miss Montenegro.

Speaking to the Guardian in Montenegro a fortnight ago, Vukadinovic, 23, said Cottrell and Farage were “very close”.

“[George] respects him so much. He always talks about him like Nigel is No 1 for him. So it’s all about Nigel. I mean earlier, it wasn’t that much, like he was mentioning him every day but it was fine for me. But the last three, four months he mentions him all the time,” said Vukadinovic, a Miss World hopeful.

Cottrell is also known for his links to the political scene of Montenegro, including the country’s now prime minister, Milojko Spajić, and his Europe Now! Movement. As Spajić was on the brink of power last year, a search and arrest warrant was sought against Cottrell in relation to accusations that he was illegally financing the party.

His lawyers said a presiding magistrate rejected the request as being without basis and “part of a political game” and described the episode as part of a political disinformation campaign because of Cottrell’s links to the insurgent politician.

Vukadinovic said Cottrell had been close to Spajić, who she had previously met in Porto Montenegro, but that they had drifted apart this year. “I don’t know why, what happened there. [George] doesn’t want to speak about that – I asked him a few times, which is weird for me,” she said.

Cottrell’s business in Montenegro is registered as a company called Private Family Office, set up under the name George Co. He used the same name on a passport when he flew by private jet last summer, according to the Montenegrin newspaper . Lawyers for Cottrell said he had official permission to use the shortened name for reasons related to his personal safety.

‘Posh George’

Cottrell, a Gloucester-born aristocrat, was privately educated on the luxury Caribbean island of Mustique followed by Malvern college in Worcestershire.

Nicknamed “Posh George” by the Brexit campaign donor Arron Banks, Cottrell was previously a volunteer for Farage in 2016, at the age of 22, after being introduced by his aristocratic uncle Lord Hesketh, a former treasurer of Reform’s predecessor party Ukip, according to Banks’s memoir.

He was with Farage on the night of the Brexit referendum when he sensed a gambling opportunity. “At 10pm, I couldn’t believe I was still getting 9/1 [for a majority leave vote],” he told the Telegraph newspaper afterwards. “We were in our campaign office and I was tracking all the major stock indices, the dollar and pound currency markets. When it got to 3am, I was getting my managers out of bed to get me another 50 grand on here, another 50 grand there, to short sterling. I just couldn’t help myself.”

Cottrell claimed to have won a six-figure sum from shorting the pound but said he promptly “lost most of it the next day” on a horse.

Later that year, Farage was present when Cottrell was arrested on money-laundering charges in the US as the pair were preparing to return to Britain after the Republican convention.

Banks’s memoir recalls that Cottrell was initially detained on the way out and they thought it was because he was “from a very wealthy family and routinely carries around thousands of pounds”.

After he was arrested, Banks wrote: “Nasty shock today as Nigel got Posh George’s full rap sheet. It’s not pretty. He’s been indicted on 21 counts of crimes including money laundering, wire fraud and blackmail.” He added that he thought Cottrell was “very young and I suspect he’s been caught up in something way over his head”.

A judge in Arizona jailed Cottrell for eight months after he ultimately pleaded guilty to one count of wire fraud as part of a plea deal under which the other charges were dropped. The crime was committed in 2014, before he worked for either the anti-EU party or Farage, who once described Cottrell as “like a son to me”.

In an interview with the Times in 2017, Cottrell’s mother, Fiona, said reports that her son was wealthy enough to have a £250m trust fund were “ridiculous, absolute rubbish”.

After coming out of prison, Cottrell talked about having made his living before 2016 working for offshore banks, including “enabling and promoting aggressive tax avoidance programmes”.

His lawyers have said he does not have access to family money, but has made his considerable wealth by working since the age of 17 – and that he no longer works for offshore banks on tax avoidance schemes but has a portfolio of investments.

After the 2017 conviction, Farage appeared to distance himself from Cottrell, saying he could not be accountable for everything people around him got up to. But the pair have been photographed together several times since then, once in 2019, again having lunch in west London in 2021 with Cottrell’s former on-off girlfriend Georgia Toffolo, a reality star and influencer, and again at Scott’s restaurant in Mayfair this year.

Vukadinovic said Cottrell had been gearing up to support Farage over the last few months but that she had no idea what his role was. “It’s something about Nigel’s campaign, that’s all I know because I don’t ask too much. I’m not really interested in that job. So he’s full-time there [in the UK] preparing Nigel for that I guess,” she said.

Vukadinovic, who met Cottrell at a bar in Tivat, where Porto Montenegro is located, three years ago, said she was present after he lost €20m in the Triton poker series, a high-stakes tournament held at the five-star Maestral casino resort in Budva on the Adriatic coast.

She said he gambled away the money over several hours in the VIP room, emerging a few times to update her. She said she left after trying to warn Cottrell, who admitted in an interview with the Telegraph in 2017 to having a gambling problem in his youth that he later kicked.

Vukadinovic, who was at the resort, said she believed Cottrell had been playing against Chinese billionaires and celebrities. “It was maybe five, six, seven hours, he was all the time on the same table [playing poker] in the private room,” she said. “He was like losing, winning, losing, winning. And I was like, ‘this is gonna be a disaster’ – and it was.”

He has also been a regular customer at the Salon Privé, a private members’ club and casino in Tivat, and has brought friends from the UK to the casino. Last year police tried to raid the casino, looking for a crypto machine. Such machines are used to buy and sell cryptocurrencies such as bitcoin.

The casino’s lawyers told the publication at the time that the crypto machine had been legally acquired for legitimate cryptocurrency trading.

Cottrell has repeatedly said he has no financial ties to the casino and company records show it is owned by a Malaysian accountant from London. Cottrell’s lawyers said he was aware of reports that a crypto machine had been imported but that he had never operated such a machine.

One businessman in Tivat described Cottrell as a friend and client since 2017 and told how he met Farage and Toffolo through him. He sang Cottrell’s praises saying: “I have nothing bad to say against him. He’s very polite, very nice and very friendly. He is a perfect British gentleman. He’s a 10 out of 10.”

Cottrell declined to comment on the record. Reform and Farage were also approached for comment.