They say success is walking from failure to failure with no loss of enthusiasm, which when you think about it, is much like the royal family’s appetite for blithely walking from scandal to scandal. The latest royal hoo-ha is a perfect example. Michael Fawcett, Prince Charles’s right-hand man, lost his job at the end of last year after being accused of selling a CBE to a Saudi businessman in exchange for £1.5 million in donations to royal charities. The cash was partly used to restore the Castle of Mey, one of Charles’s Scottish properties.

Charles is so close to Fawcett that he once said: “I can manage without just about anyone except Michael.” Fawcett’s roles as valet reportedly included squeezing out toothpaste from a crested silver dispenser onto the royal brush, and holding a vial of the heir’s urine during a doctor’s appointment. One hopes the money for these degrading tasks was worth it, and did something to offset any job-induced daydreams of dusting off the 200-year-old blueprints for a certain French contraption made mostly of wood with a small but significant amount of metal.

Royal scandals involving money, access, and influence date back a long way – we could really begin with Henry VIII and the dissolution of the monasteries – so as an introductory guide, here are the top five sleaziest deals the Windsors have been embroiled in. See you for the next one!

The fake sheikh – a legendary undercover reporter for the News of the World named Mazher Mahmood, who often posed as a Gulf tycoon – pulled off an excellent sting of the Duchess of York. Pretending to be a businessman, he caught her on camera offering £500,000 for a face-to-face meeting with Prince Andrew. That money, she bragged, would be able to “open up all the channels, whatever you need”. “You will be his friend”, she told the journalist in 2010. She walked away with $40,000 in cash as a downpayment, and said: “Look after me and I’ll look after you… you’ll get it back tenfold.”

Fergie also hinted that Mahmood would be able to exploit the connections Andrew made as a member of the royal family, claiming: “He meets the most amazing people and he just throws them my way.”

She also complained that her divorce settlement from Andrew in the 90s left her skint. “I have not a pot to piss in,” she moaned, adding that if she got a “lick of the spoon” with this half-a-million pound deal, it would “save her bacon”. In a tearful interview with Oprah later that year, she said she had been living beyond her means and succumbed to temptation in an “act of such gross stupidity”.

In the noughties, Prince Harry was such a bad student at Eton that the staff had to finish his A-level art course for him, according to a former teacher. He put in such little effort into his final project that one teacher prepared an explanatory note to accompany Harry’s images, while another fitted them into his creation. Sarah Forsyth, a teacher at Eton, said Harry’s poor academic record was well known, and that her colleagues were “desperate” to find anything redeemable about his work that they could give marks. She claimed unfair dismissal from the school and won damages. There’s no suggestion he was involved in teacher collusion, but in the end – after all that faff – he only got a B. In Art!

Accusations about Prince Andrew’s financial impropriety are the least of his worries now that his association with a deceased billionaire paedophile is being probed by US authorities. But once upon a time his use of private jets and helicopters to make short trips was among the worst known things about him. He once choppered from Royal Lodge in Windsor to a golf course in Kent to spend an hour at a party – at an estimated cost of £2,000. A train would have cost him £30. A private jet for a four-day trip to Azerbaijan cost £60,000. That was during his role as a UK trade envoy, during which his business trips seemed to coincide with golfing sessions and private holidays. Simpler times.

To Russia, with love from Prince Michael of Kent

The Queen’s first cousin Prince Michael, whose wife once bemoaned their financial situation (while living in Kensington Palace), was exposed earlier this year for selling access to Vladimir Putin. The Sunday Times and Channel 4 posed as a foreign company looking for access to Russian markets, and Michael was only too happy to oblige. Michael’s friend and business associate, the Marquess of Reading, asked for £50,000 (a knockdown price considering what Fergie asked for) in exchange for introducing the undercover reporters to Putin’s inner circle. The marquess said he “overpromised” and was “truly regretful”, while Prince Michael said he had not met Putin since 2003.

Just while we’re on the subject of the Kents, Princess Michael of Kent was once caught by the fake sheikh for making some dodgy comments to try to sell her £6m country pile in the Cotswolds. She claimed that she was a skilled interior designer, a writer, and a lecturer, and tried to sweeten the property deal by throwing a white tiger, courtesy of Siegfried and Roy.

Two-thousand-and-five was a bad year for the princess. A few months earlier, she gave an interview to a German newspaper defending Prince Harry’s decision to attend a fancy dress party as a Nazi, saying the British press “has a different sensibility because of its ownership structure”. It’s hard to imagine this meaning anything else except an allusion to the antisemitic conspiracy theory about Jewish influence in media and business.

Princess Michael has also decried how the English “take the breeding of their horses and dogs more seriously than they do their children”, adding “their children marry everywhere”. And she allegedly told a group of black diners in a New York restaurant to “go back to the colonies”. This may have undermined the apology she later made in 2017 after attending a Christmas dinner with Meghan Markle. Princess Michael saw fit to arrive wearing a brooch with a blackamoor figure on it. Oof.

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