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The most outrageous business expense claims from across the globe

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Maritime historians and naval archivists have recently discovered the world’s oldest expenses claim, submitted by Captain James Cook in 1771. The claim was found by a team taking part in a global search by webexpenses to find the world’s oldest expense claims.

The historic receipt was discovered when searching through long-forgotten old naval records in Plymouth. The claim appears to have been submitted by Cook on his return to Plymouth and details a number of items he picked up during his exploration of the Pacific.

Items listed include cartography equipment such as an A-Z of the Pacific Ocean, as well as claims for lost boomerangs and food for a pet kangaroo.  

The claim by Cook joins other notable finds, including a claim by Charlie Chaplin for a five-pack of stick-on moustaches, a new top hat and numerous walking sticks; Alexander Graham Bell’s first claim for “business telephone calls” and several claims made by Alexander Fleming for petri dish cleaner.

I don’t know about you, but expense claims for lost boomerangs and kangaroo food would arguably now be considered ridiculous to make. That being said, there are people from all walks of life who are prepared to push the envelope on expenses. 

We have been digging out some of the most outrageous claims from around the world – the vast majority of which have been accepted as falling within the rules – and here are five of our favourites. 

(1) Believe it or not, breast implants are tax deductible

Just because you incur expenses for business reasons doesn’t mean that they automatically qualify as deductible – they must be “ordinary and necessary” in relation to your business.

Moreover, the law generally categorises what you spend to improve your appearance, general health or sense of well-being, as nondeductible personal expenses. It should come as no surprise then that lots of business-versus-personal disputes wind up being resolved by the courts.

A case in point is that of Cynthia Hess, known as “Chesty Love” in her show biz endeavours as an exotic dancer. Hess had just launched her topless career on the night club circuit, but she suggested that because of a hereditary deficiency leaving her not as well-endowed as some of her rivals, she earned significantly less.

Her agent thus persuaded her to enlarge her bust size to 56FF and then to 56N – those are real numbers!

She then persuaded the United States Tax Court to uphold a deduction for the surgical implants to enlarge her bosom – which the judge allowed.

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(2) Never try to deduct your gambling losses as business expenses

Giuseppe Tarascio, a Canadian phone-company technician, bet on some creative tax accounting, but lost his appeal in court. He tried to deduct more than $96,000 in gambling losses as business expenses.

Furthermore, he tried to back them up with proof. Tarascio kept records of his gambling and touted his “special knowledge and skill as a gambler” in trying to claim casino and horse-betting losses as business expenses. 

Tarascio “had little by way of a systematic method for gambling and spent no time practising his skills,” the appeals judge wrote in his decision. And his recordbooks were created solely for the purpose of supporting his tax-deduction claims – not in the regular course of business.

The judge even discounted Tarascio’s argument that his degree in mathematics and training in probability theory bolstered his claim that gambling was his business.

Read on to find out about the expenses claim that uncovered an affair.

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