In the end it was the tax that did him. In 1931, infamous Chicago mobster Al Capone was convicted of tax evasion following a US Treasury Department investigation. Capone was sentenced to 11 years in prison, fined $50,000, charged with paying the $7,693 court costs and ordered to pay $215,000 plus interest due on back taxes. Capone served seven years, six months and 15 days of his sentence, first in the US Penitentiary in Atlanta and later in Alcatraz, having paid back what he owed.
The English jockey is a nine-time Epsom Derby winner, the first of which earned him the title of youngest champion at only 18 years old. His career hit a significant hurdle in 1987, however, when he was sentenced to three years in prison for tax fraud of up to £3.25m over 14 years. He reportedly funnelled the money under different names into accounts held in Singapore and the Bahamas. It was the biggest individual income tax-dodging case ever brought in the UK at the time. Piggot retired from racing in 1995, with an estimated personal fortune of £20m.
Take That member and songwriter, Gary Barlow along with bandmates Howard Donald and Mark Owen and their manager Jonathan Wild, was forced to pay back more than £20m after investing £66m in Icebreaker, a fund which was ruled to be a tax avoidance scheme by the First Tier Tribunal in 2014. Following public calls for his OBE to be removed, Barlow tweeted, “I want to apologise to anyone who was offended by the tax stories earlier this year.”
A US institution with an impeccable public image, Stewart had helped people with their homes and lifestyles since 1982. But in 2005 it came crashing down when she was sentenced to five months in jail for insider trading and was ordered to pay $220,000 (£169,118) in back taxes and penalties to the New York State. The court heard that Stewart sold shares in cancer drug manufacturer ImClone after receiving a tip-off that its central drug had failed to receive approval, prior to the FDA being informed. She was also fined for not paying tax on her East Hampton mansions.
Paul Manafort and Michael Cohen
Donald Trump’s presidency has been quite eventful, but the news that his former campaign chairman Manafort and “fixer” Cohen were charged with several counts of fraud still managed to shock. In the space of a few minutes in two separate US courtrooms, Manafort was found guilty of five counts of tax fraud, two counts of bank fraud and one count of failure to report a foreign bank account, while Cohen pleaded guilty to eight counts of tax evasion, making false statements to a bank and campaign finance violations. Cohen implicated the president by stating under oath that he paid “hush money” to silence two women at the direction of the then-candidate.
The Portuguese football superstar recently reached an agreement with the Spanish tax authorities for a two-year suspended sentence and a €18.9m (£17m) fine after being accused of hiding revenues generated from his image rights. The agreement was reached despite his representatives stating that Ronaldo “never had a tax problem, contrary to what the Spanish prosecutors insinuate”. He has since departed Spain, from Real Madrid to Italy’s Juventus. Not to be outdone, rival Lionel Messi was also sentenced to 21 months in prison last year and fined €2m (£1.7m) after being found guilty of three counts of tax fraud.