The more that comes to light about Sir Bradley Wiggins’s sad descent into bankruptcy, the more people are asking where it all went wrong for the face of Britain’s greatest sporting summer.

News that claims against Wiggins’s estate have doubled to almost £2 million did little to allay fears for a man who seemed to have the Midas touch only to lose “absolutely everything” and be forced into alleged “sofa surfing”. This from someone who sat on a throne after winning the Tour de France and Olympic gold in 2012 before proclaiming: “It’s never, ever going to get any better than that.”

The tale of how the 44-year-old amassed and lost an estimated £13 million fortune can be traced back almost two decades to the launch of the image-rights firm he now blames for his downfall. Wiggins had yet to win the first of his Olympic titles when he, his soon-to-be-wife Catherine, and his mother Linda, set up Wiggins Rights Limited on June 28, 2004.

Image rights companies have long been utilised by those in the public eye as they are often taxed at a lower rate than applies to most income. But, by the end of its first year, which included Wiggins claiming the Olympic individual pursuit title, shareholders’s funds held by Wiggins Rights totalled just £4,176. The company went on to report a loss on an almost annual basis as Wiggins struggled to translate his cycling success into pounds and pence.

That was until he won double gold at the Beijing Games, after which he signed with leading sports marketing agency MTC and joined road-racing team Garmin-Slipstream in 2009 on a reported wage of £350,000 annually.

This, and his move to Team Sky the following year on what is said to have been a £3 million salary, coincided with Wiggins Rights banking hundreds of thousands of pounds. He also signed a six-year clothing deal with fashion brand Fred Perry shortly before his Tour de France triumph, crowning glory at London 2012, coronation as BBC Sports Personality of the Year, and subsequent knighthood, upon which shareholder funds in Wiggins Rights surged into the millions.

Yet, it was also after becoming the first man to win the Tour de France and Olympic gold in the same year that the first cracks emerged in the Wiggins empire. He sacked MTC in 2013 amid a bitter dispute over a bill for a percentage of his earnings, of almost £750,000, that sparked a lawsuit and countersuit that were ultimately resolved with an out-of-court settlement.

He also ran into trouble over a charitable foundation he set up shortly after London 2012, when he was forced to cover tens of thousands of pounds of losses out of his own pocket and the Charity Commission announced it would remind trustees “of the need to be open and transparent” amid concerns about how the foundation was spending its money. Wiggins said in 2015 the foundation was being wound down, adding: “I’m a racer not a fund raiser you know.”

Around the same time, Wiggins became caught up in an ongoing HM Revenue and Customs crackdown on what it claimed was the misuse of image-rights firms, something he revealed in a recent appearance on Lance Armstrong’s podcast, The Forward.

“When I started with Team Sky, as most cyclists are, I was self-employed with an image-rights company,” he said. “Towards the end of my tenure with Team Sky, they were involved in a two-year case with HMRC, for everyone who worked at Sky, to fight whether they were deemed employed by Sky. So, I was acting as a witness for Sky in that case against HMRC, spent an enormous amount of money on legal fees in supporting that. In the end, they [said] I was deemed employed. So, I had to go back five years and pay all the taxes and every bits and bobs and pieces. So, that had huge ramifications.”

After ditching MTC, in November 2013 Wiggins joined XIX Entertainment, set up by former Spice Girls manager Simon Fuller and at that time home to, among others, David Beckham and Andy Murray. A joint venture between Wiggins Rights Ltd and the agency, called 101 Ride Limited, was immediately formed, with shares divided on a 75-25 split and Wiggins’s wife and a representative of XIX appointed as directors. That led, less than a year later, to the creation of Wiggins’s own cycling team via the formation of a third firm, New Team Cycling Ltd, of which he and the same XIX representative were the directors and 101 Ride Ltd the parent company. As Wiggins told Armstrong in August, this added a further layer of complexity to his business affairs, as XIX set up what he called “joint ventures with various clothing companies, drinks suppliers, all different things, whatever endorsements”.

He added: “These companies were all subsidiaries of the top company – my image rights company. As we see now through the lawyers, that was done purposefully so the top company would always take the hit if there was any trouble in the other ones. They should have been separate companies.”

Problems began when Team Wiggins – which Wiggins said “was set up to facilitate the national track programme, which was the team pursuit, which was my last cycling career goal in Rio” – began making unexpectedly heavy losses.

“That team, which was being managed by XIX Entertainment – and run on a daily basis along with Andrew McQuaid, who was the manager of that team – all the salaries came out of. The budget was £650,000. But, in year one, for six riders, it spent a million, so I had to prop that team up with my own money from Wiggins Rights. So, there was a lot of money coming down from the top company to prop up these ventures. Off of that, your management were taking slices off from their expenditure and people they were putting in place. And because they were all subsidiaries of the one company, the top company took the biggest hits. And it ran up a debt of nearly £1.5 million, which was given to me as a director’s loan. But I wasn’t the director at the time, and I had to be made a director to take the loan without my knowledge. I was still racing my bike at the time. So, it’s a complete mess, and I wasn’t aware of the mess until I was deep in retirement.”

Telegraph Sport has approached XIX Management for comment.

When Team Wiggins launched in 2015, Wiggins was still riding high. Shareholder funds in Wiggins Rights peaked that year at £2.6 million and he went on to sign a deal with Halfords to launch a new range of eponymous children’s bikes. He then made a glorious return to the track at Rio with his fifth Olympic gold.

It took barely a month for the shine to be taken off that. A group, “Fancy Bears”, hacked into and leaked the anti-doping records of a host of Team GB and US competitors. The cache included documents showing Wiggins had been given permission under the medical-exemption system to take two banned substances shortly before the Tour de France in 2011 and 2012 and the 2013 Giro d’Italia. The revelation was quickly followed by the “Jiffy Bag” affair and accusations that rules had been broken over the delivery of a mystery package allegedly intended for Wiggins ahead of the 2011 Tour. A subsequent investigation by MPs ruled Team Sky had “crossed an ethical line” in its use of medical exemptions for performance-enhancing drugs. Both Wiggins – who retired from professional cycling in December 2016 – and Team Sky denied any wrongdoing.

The scandal appeared to have less impact on Wiggins’s finances than, ultimately, the launch of Team Wiggins after he signed a three-year partnership with car manufacturer – and former bicycle company – Skoda, that included him receiving a vehicle.

Having plunged to £873,333 shortly before Rio 2016, available funds in Wiggins Rights had recovered to £1.03 million, according to accounts for year end June 2017. In September of that year, a personalised motorhome commissioned by Wiggins sold for almost £50,000 at auction, demonstrating the continuing pull of the “Wiggo” brand. Two months later, he paid £885,000 for a five-bedroom barn conversion with an indoor swimming pool in rural Lancashire.

But any hopes of an idyllic retirement were soon dashed when he became the first celebrity named as having invested in the notorious “Cup Trust”, which had previously been investigated by MPs who described it as having been “set up as a tax-avoidance scheme by people known to be in the business of tax avoidance”.

The scheme was shut down by the Charity Commission in 2017 but that did not prevent calls for Wiggins to be stripped of his knighthood over his involvement. A spokesman for Wiggins said that he “settled all tax liabilities a number of years ago and has paid all taxes due”. He added there were “no open inquiries with HMRC”.

Unfortunately for Wiggins, that was soon about to change in devastating fashion. His relationship with XIX had reportedly begun to sour post-retirement and, in January 2017, it was announced he had signed with M&C Saatchi to “focus on broadcasting and developing my own brand”. His final ties to XIX, via 101 Ride and New Team Cycling, were severed in March 2018. By June of that year, available funds in Wiggins Rights had dropped to £461,681. Those were the last accounts filed before it was announced that Team Wiggins would fold at the end of 2019. In the meantime, Wiggins attempted an ill-fated sporting comeback as a rower and signed a podcast deal with Eurosport that expanded into a punditry role for the network’s grand tour coverage. That included providing in-race analysis from the back of a motorbike. He also said he was retraining as a social worker.

None of this enabled him to honour his debts, including to HMRC, which lodged a bankruptcy petition against him on January 21, 2020, over a tax bill that went on to total more than £300,000. The petition was dismissed at a five-minute hearing that July after Wiggins agreed a payment plan it later emerged involved entering into an individual voluntary arrangement (IVA). It was quickly followed by the liquidation of the companies set up by him and his wife – with whom, he announced that May, he had split – with debts of around £1 million. Liquidators then set about trying to reduce the figure by selling assets, including offering the trademark to Wiggins’s own name and nickname.

Wiggins continued to work for Eurosport until the end of 2022 before indicating he wanted to quit punditry. He also went public with sexual abuse accusations against his former coach, Stan Knight, who had since died.

Around the same time, a “notice of breach” was issued in respect of his IVA after he was unable to keep up with payments, ultimately leading to him being declared bankrupt on June 3 this year. Overnight, Wiggins was faced with the prospect of having to sell assets that included his home, a holiday property in Majorca, and all his medals, trophies and other memorabilia – although he previously said he had “smashed” his knighthood and Sports Personality gong to make a point to his children about their real value. The bankruptcy prompted his lawyer, Alan Sellers, to proclaim Wiggins had lost “absolutely everything” and had been “sofa surfing”, something Wiggins disputed when talking to Armstrong.

Sellers was also quoted saying Wiggins’s Lancashire home had been seized and sold, although Land Registry records indicate that any such sale has yet to be completed. When it emerged last month that claims against Wiggins’s estate had doubled to almost £2 million, Sellers told Telegraph Sport he thought the home had been sold. He also revealed “no decision” had been taken about the fate of his client’s medals. Sellers indicated Wiggins may be subject to an income payments agreement or order under which a percentage of fees he earned from the likes of speaking engagements and media work would be paid towards his bankruptcy. But he said he suspected the bulk of Wiggins’s debts would never be repaid. He described Wiggins’s plight as “a very sad state of affairs” and a cautionary tale about “where things can go wrong for professional sportsmen”. He added: “He’s not the first and, I suspect, he won’t be the last, sadly.”

Bankrupts are ordinarily discharged after a year but a liquidators’ report into Wiggins Rights in September said it could be another 24 months before the affairs of Wiggins’s estate were in order.

The saga has left Wiggins trying to rebuild his life, something Armstrong has offered to help with by funding therapy in the United States. “You know, we’re talking about therapy,” Wiggins told the latest edition of the High Performance Podcast, hosted by former BBC and TNT Sports presenter Jake Humphrey and therapist Damian Hughes. “He [Armstrong] wants to pay for me to go to this big place in Atlanta, I think it is, where you stay for a week, they take your phone off you, and Lance was going to fund that for me.”

Wiggins told Cycling News last year that “professional negligence” was to blame for his financial difficulties and that “there’ll be a number of legal claims from my lawyers left, right and centre as a result”. There is nothing to indicate there had been any such “negligence” by McQuaid – who now manages Wiggins’s cyclist son Ben – XIX, MTC, or M&C Saatchi, which he left at the end of 2021. Sellers, meanwhile, confirmed such legal claims could no longer be made without the consent of the trustee of Wiggins’s bankruptcy, Kevin Murphy of Begbies Traynor.

Murphy declined to comment, while attempts to contact a spokesman for Wiggins went unanswered, leaving the Armstrong podcast the only occasion he has gone into detail about his financial plight.

“One of the things I regret is I never paid attention to my financial affairs when I was racing,” Wiggins told Armstrong. “I never did the sport for the money, but I realise I should have paid more attention to it. Because I was getting ripped off left, right and centre by the people looking after me, accountants as well. Which is one of the things that happens to athletes, you know, you make a lot of money and if you haven’t got your eyes on it, people take advantage.

“And this will all come out in the wash over the next few years. It’s just going to be a hell of a headache to get right.”