In many ways, a contemporary art gallery has a lot in common with a courtroom. Both are places of high spectacle, of lofty judgement, enforced decorum and politesse. People dress up to attend both and often leave owing vast sums of money (possibly overcast with fear or shame). It has always seemed odd to me, therefore, that when art dealers end up on trial, they do such a good job of looking out of place, of seeming shocked to be there. A good blue suit, it seems, will only get you so far.

Art dealers are synonymous in the public imagination with big money and dastardly behaviour. (I once briefly dated a woman whose family beseeched her to break up with me solely because I owned an art gallery.) And so, when considering how to pull off a fine-art swindle, it can be a little difficult to choose from the bright and varied palette of available criminality. Cicero wrote, “To be ignorant of what came before you is to remain forever a child.” Fortunately, the history of art-market criminality provides us with plenty of lessons in deception and scurrility.

When I tell people that I’ve recently published a book about fraud in the art market, their questions tend to go straight to art forgery. They picture a little old man in a remote Tuscan village, painstakingly putting the finishing touches on an as yet “undiscovered” Leonardo. This new-old painting then makes its way to market via a network of beret-wearing scallywags, all of whom smoke ominously and from the sides of their mouths, despite the conflagratory risk to their precious cargo.

This image comes, of course, from Patricia Highsmith novels and Hollywood movies starring hirsute billionaires, but it does have roots. One such forger (Dutch rather than Italian) was Han van Meegeren, the most prolific and successful forger of Vermeer paintings. Van Meegeren was canny in his choice: not only were Vermeer paintings incredibly valuable and sought-after but there were also very few of them (there are probably only 35 in existence). The discovery of “new” works by the Dutch master was welcome news to gullible buyers. Working from the basement of his house on the French Riviera, Van Meegeren used Bakelite to form an authentic-looking craquelure on his paintings.

Van Meegeren is remembered in the Netherlands as something of a national hero. During the Second World War, Hermann Göring traded 137 looted Dutch paintings for just one of Van Meegeren’s fake Vermeers. Van Meegeren thereby helped to safeguard precious national heritage – and got one over on the Nazis. After making and selling more than a dozen fakes (and becoming hugely wealthy in the process), Van Meegeren was caught and put on trial. He died in 1947, months into his prison sentence, at the age of 58.

What Van Meegeren did right was to select an artist to forge whose work was scarce. Half a century later, however, Iranian-American Ely Sakhai pulled off a fraud scheme with a brazenness that employed the opposite approach. Sakhai, who speaks fluent Japanese, knew that what most concerned new collectors in Japan was authenticity. So he trawled the auction houses of Europe and America, exclusively buying minor works by major impressionist artists, from Monet to Renoir, that came with certificates of authenticity. He would then have the painting expertly copied and sell the facsimile, along with its original’s certificate, to a Japanese collector. This went on until one of the buyers decided to sell, and a sharp-eyed auction-house employee in New York spotted what appeared to be the same Gauguin painting for sale in two different auctions, continents apart.

What elevated Sakhai’s scheme above that of a forger such as Van Meegeren was that it exploited a weakness in the art market of its day. Collectors, especially new ones, knew next to nothing, and with no internet databases available, they were flying blind, forced to trust their dealers. These days, with the price of practically every artwork that sells at auction available online, you must become ever more creative if you’re going to pull off something lucrative.

Perhaps part of the reason why forgery is the art crime that first comes to people’s minds is that it at least involves some artistry. But contemporary art, which is where the money is, is too tricky to fake; for one thing, the artists are often still alive. Nowadays, art crime has gone the way of the market, and it is increasingly financialised. As Damien Hirst once said, “Art’s about life; the art world’s about money.” Today art is all about the money.

All this is to say that art fraud today is, by necessity, a far trickier beast; one that is more contractual sleight of hand than imitated brushstroke. Take my former friend and business partner Inigo Philbrick. His fraud scheme, which clocked in at more than €79m, is thought to be the largest in US history. The swindle was wildly complex – like a Hollywood bank heist but carried out over emails and Whatsapp. The simplified version is that he would sell the same painting, or shares in that painting, to multiple people. In one instance, Philbrick sold 220 per cent of one multimillion-dollar painting – obviously 120 per cent more painting than exists.

There are several things to analyse here. Since art has become an asset class of its own, dealers and collectors have begun to buy works that they have no intention of hanging in their galleries or penthouses. Instead, the artworks languish in tax-haven warehouses until they have increased sufficiently in value. These kinds of buyers also often buy percentages in paintings to mitigate risk. Philbrick kept physical control of these paintings, ostensibly so that he would be able to arrange a client viewing at the drop of a (top) hat, but in reality so that he could sell the same work over and over. And what happened when two buyers both wanted control of a painting they owned (or thought they owned)? Philbrick simply sent them a blank canvas in a crate to their Swiss warehouse, where it remained unopened.

There are many different ways in which you can pull a fast one in the art market, though as with many get-rich-quick schemes, you’re more likely to end up counting the bars on your prison-cell door than your fortune. We’re fascinated by hucksters and villains but to me this seems a great sadness when it comes to the art world. When we obsess over fraudsters and their grimy actions, we forget ourselves. But perhaps our preoccupation with art crime also tells us how important art really is, how it can enrich us far more than mere lucre. We would do well to remember that.