Former Premier League star Dean Windass earned £30,000-a-week at the peak of his football career, but was among those to have been declared bankrupt following retirement from the game.
Windass, now 56, had enjoyed an 18-year playing career and featured in each of English football’s top four divisions.
The forward represented three different clubs in the Premier League, featuring for Bradford City, Middlesbrough and his hometown club Hull City.
His is best remembered for his stunning goal in Hull City’s Championship play-off final triumph in 2008 which sent the Tigers into the Premier League for the first time.
Windass announced his retirement from the game in 2009, before a brief spell pursuing a managerial career. He was dropped by Sky Sports as a pundit in 2012 after he crashed his car while drink-driving, which he told Daily Mail Sport earlier this year was his ‘biggest regret’.
Just four years later Windass, who has spoken about his battles with alcohol and depression, was declared bankrupt over a £150,000 tax debt.
Former footballer Dean Windass has opened up on reasons players find can find themselves in financial difficulties after their careers end
Former striker Windass was declared bankrupt just seven years after retiring from the game
In a recent interview with The Athletic, Windass opened up on his bankruptcy and identified how footballer’s earning significant weekly wages can find themselves in financial distress.
Windass, who still pays HMRC £500-a-month, pinpointed an investment made during his playing career. Rather than proving an earner that could help his post-playing career, the investment would ultimately become a financial weight for Windass.
‘I was playing for Middlesbrough in 2001 and we had someone come to the training ground offering the chance to invest in the film industry,’ Windass told The Athletic.
‘I didn’t know much about it but I looked on this form and there was every celebrity you could think of that was part of it. I’m thinking, “If they’ve gone into it, I’ll get involved”.
‘I invested thinking that, after 15 years, I’d get this nice lump sum. The years went on and I kept getting these brown envelopes through the door. I was thinking, “What the bloody hell is this?” To cut a long story short, I got a tax bill for £164,000.
‘I paid 40 per cent tax throughout my career when earning your big money. I wasn’t a tax dodger, I just went into the wrong scheme. I look back now and obviously it was a bad decision.’
Windass was among a number of former players stung by investing into the film investment scheme, while he admitted he had lost ‘a lot of money’ in his divorce from his former wife Helen.
He claimed there are a ‘high number’ of players who have ended up bankrupt after going through divorces.
While Windass earned around £30,000-a-week at the peak, a financial investment he made during his career would ultimately prove to become a weight following his retirement
Windass is far from being alone, with a number of former Premier League players having been declared bankrupt following their retirement from the game.
Former England internationals Trevor Sinclair and Shaun Wright-Phillips were among the latest to find themselves facing bankruptcy proceedings.
Sinclair, who won 12 England caps during his career, was declared bankrupt after ‘burying his head in the sand’ over a £36,000 tax debt.
HMRC stated that Sinclair had failed to pay taxes and penalties totalling £36,424 in relation to his pundit work. The 52-year-old had previously been given extra time to come up with the money or alternative proposals to pay.
Wright-Phillips was hit with a bankruptcy petition in June. A representative told Daily Mail Sport at the time: ‘Shaun is not aware of this and matters are already with his accountant who is fully versed in Shaun’s affairs. He is currently out of the country and the matter will be strenuously contested on his return.’
His record on Companies House, under the name of Shaun Cameron Wright-Phillips, shows ventures with six companies, five of which have been dissolved. The most recent of those, VisionPro Sports Europe, was dissolved in 2018.
Elsewhere, last year, former England striker Emile Heskey paid was ordered to pay £200,000 in unpaid tax, after being involved in a celebrity investment scheme that was at the centre of a £700million tax dispute.
Specialist costs judge Mark Whelan said the figure was ‘reasonable and proportionate’.
Former England international Trevor Sinclair, pictured in 2017, was made bankrupt in June
Shaun Wright-Phillips was reportedly hit with a HMRC bankruptcy petition in June, with his representatives stating he will ‘strenuously contest’ the matter
It followed Heskey being hit be 15 penalty notices issued in 2005. He had been due to face a trial in the High Court in 2019 after he had been hit by a bankruptcy petition that was filed by HMRC, but it did not take place after he admitted liability for the debt.
In 2023, it had been previously reported that Heskey – who was worth £12m at he peak of his career – was found to have defaulted on £92,000 of tax while working as football development officer between 2017 and 2020. He was fined £42,000.
A celebrity bar he ran with his wife Chantelle in Alderley Edge was shut down by the High Court with debts of £163,000 in May 2023. The bar, called Parea, was opened in 2018 to serve the numerous footballers and WAGs who lived in the Cheshire enclave.
Meanwhile, in 2014, former England goalkeeper David James was declared bankrupt despite earning an estimated £20m during his long career which included 805 club appearances and a further 53 for England.
He faced an expensive divorce in 2005 which cost him an estimated £3m. At one stage, he was earning £50,000 a week.
Yet, he was later forced to auction his entire record collection and sporting memorabilia in an effort to discharge his bankruptcy.
Windass’ assessment of issues facing footballers were shared by former Manchester United and England defender Wes Brown, who was declared bankrupt by HMRC back in 2023.
Brown was a five-time Premier League winner, also won the Champions League twice and earned 23 England caps during his career.
Emile Heskey was ordered to pay £200,000 in unpaid tax last year, after being part of a celebrity investment scheme that was at the centre of a £700million tax dispute
In 2014, former England goalkeeper David James was declared bankrupt despite earning an estimated £20m during his long career which included 805 club appearances
Despite his success on the pitch and earning around £50,000-a-week at one stage, Brown’s financial struggles were put down to his company collapsing, bad property deals and overpaying on a farm.
Brown has since admitted he did not have the ‘right people’ to guide him during his younger years.
‘I think the main thing is when you are making a lot of money, you need the right people, don’t you? And I would say that’s one of the things I didn’t have,’ he said on the Ben Heath Podcast last year.
‘It was a little bit different. It wasn’t lots of people you go and speak to and you maybe meet people and do this do that. I wasn’t interested in any of that. You said yes and got on with it.
‘It’s a long story and I won’t go into the detail, but it’s stuff that happened a long time ago with certain investments and getting into stuff that as a young kid, a lot of people go into, [but] don’t really understand it.
‘It’s what a lot of people are doing and then it came to a head last year, and that’s how it went. It’s happened and I’m just getting on with it but it’s one of those things where you hope people, especially this generation, don’t get involved in.
‘I’ve had a lot of players that have said “I’m in the same thing”. I won’t say names and it doesn’t necessarily mean that the same outcome will happen to them.
‘But it’s stuff like when you’re kids you don’t really understand it anyway, you just assume a lot of people are doing it and it’s fine. That’s not your life, you’re just playing football.
Former Man United defender Wes Brown has spoken about how did not have the ‘right people’ to guide him during his career, after he was declared bankrupt back in 2023
Brown (right) has since become an ambassador of a company founded by former Man United and England captain Bryan Robson, which looks to provide financial advice to players
‘A lot of people have been able to get themselves out of it or they’re still involved in sorting it out or whatever, but I just couldn’t. There’s not much I could do.’
Brown, who works for Man United as an ambassador and was present on the club’s post and pre-season tours this summer, has looked to help others following his own financial troubles.
The 45-year-old became an ambassador for High Performance Individuals in 2022, a company founded by ex-Man United and England captain Bryan Robson.
The company offers financial management and guidance, with Robson declaring that he had grown ‘sick of seeing mates in the media all the time, bankrupt and making bad decisions’.
Speaking to Daily Mail Sport last year, Robson admitted he had been stung a couple of times during his own career, including being encouraged to invest in a hotel in Canada that he later discovered did not exist.
Robson’s company was founded to support players, with an estimated 40 per cent of professional footballers go bankrupt within five years of finishing playing.
Among the challenges identified were the fluctuating incomes of players during their careers, the short career spans, fraudsters targeting high-profile individuals and post-career planning requiring careful guidance.
Former Liverpool winger Ryan Babel has identified similar issues after serving an an ambassador for the Dubai-based company Sport Legacy, which offers financial advice.
He pinpointed the lifestyle led by players as a factor, along with the risks of being ‘used as an ATM’ by various hangers on, who have attached themselves to stars during their career.
It is hoped that increased financial advice to players, including from the Professional Footballers’ Association, can help limit the number of former stars facing financial strife in the future.
