As the art world descended on Venice for the opening of its prestigious Biennale last week, the talk was of an industry at the peak of its powers. Such global extravaganzas, together with the big-money fairs and auctions, have transformed the art market. What was still a rarefied, slightly niche business at the turn of the millennium has evolved into a juggernaut with estimated total annual sales running to $65bn. Venice’s rich displays of art, old and new, now compete with parties in private palazzi and on billionaires’ boats.

Yet the market has a problem. For all the thousands of visitors to its sparkling events, traders are struggling to convert the next generation of enthusiasts into committed buyers. The sense that an overhyped market has hit a wall is captured in a crop of new books that illuminate some of the darker sides of the art world.

Persistent opacity around issues such as prices, ownership and condition reveals the limits of a market with no overarching oversight, and which still often relies on handshakes and hidden codes of conduct. Such grey areas have proved a playground for schemes ranging from opportunistic speculation to the downright criminal.

Recent scandals, while at the extreme of the largely legitimate and often mundane market, illustrate the need to question the status quo. In the past year alone, art adviser Lisa Schiff — who counted actor Leonardo DiCaprio among her clients — stands accused of running a Ponzi scheme amid legal claims that she owes other collectors nearly $7mn; art dealer Guy Wildenstein has been found guilty of tax fraud, sentenced to four years in prison and fined €1mn; and British artist Damien Hirst has been revealed to have backdated some recent works to his 1990s heyday. All this against a backdrop of the art world’s blind craze for cryptocurrencies and digital assets, with fortunes rising and falling in a matter of months.

The most sensational story so far has been that of Inigo Philbrick, an art dealer who flew too close to the sun — literally so, absconding to the south Pacific island of Vanuatu to hide from mounting legal claims before his FBI arrest there in 2020. Philbrick pleaded guilty to an audacious $86mn wire fraud scheme that took in collectors, investors and fellow dealers, and was handed a prison sentence of seven years.

Taking on his story is his erstwhile friend and colleague, Orlando Whitfield, with whom Philbrick had originally plotted to collaborate on a magazine feature to put across his side of events. Once Whitfield saw the paper trail documenting his friend’s behaviour, he wisely decided to go it alone. All That Glitters is the result.

Book cover of All That Glitters by Orlando Whitfield

Philbrick emerges as tough to turn down. Variously charming, persuasive and hare-brained, this is a portrait of a narcissist, always ready to star in the film of his life. “I don’t think failure ever even occurred to Inigo,” Whitfield notes. In a seemingly unchecked arena, his actions included creating a fake client and managing to sell 220 per cent of one artwork, a 2012 painting based on a photograph of Pablo Picasso by the briefly in-demand Italian conceptual artist Rudolf Stingel. (While it is more usual than many might realise for a hugely expensive painting to have more than one owner, obviously only 100 per cent of it is ever legally available.)

Alongside Philbrick, Whitfield, with a hefty dollop of British self-deprecation — he is described as “a failed art dealer” in the book’s brief blurb — comes through as the willing victim of his friend’s personality disorder. The book records his memories of 15 years of their unbalanced friendship, from meeting in their twenties at London’s Goldsmiths art school in 2006 through to intermittent conversations during Philbrick’s incarceration.

What the mismatched pair share, poignantly, are divorced parents and successful art-world fathers whom they were wired to impress — Philbrick’s was a museum director; Whitfield’s an auctioneer.

Some of these escapades seem barely believable. Whitfield admits he came to doubt many of Philbrick’s stories, including one in which the instinctive dealer buys a watch at one end of London’s Burlington Arcade then immediately resells it at the other end, making £500 in less than an hour.

More worrying for the art market is the potential for scams now that today’s buyers are more speculators than art lovers and don’t even see the works into which they park their millions. Philbrick sold another Stingel — one of his gold paintings in “hushed AmEx tones” — to a client and then, for $2.5mn, on to a joint venture that he himself ran with one of his early mentors, the esteemed White Cube gallery founder Jay Jopling.

Philbrick had originally bought the work for $300,000 because, as he knew, it was damaged to the extent that the artist wanted it destroyed. No one else knew the score and, unable to persuade his usual conservator to restore it, Philbrick found three people to execute a good-enough touch-up in a garage in London’s Mayfair. The work then got a clean bill of health (albeit unknowingly to the wider world) as “now a Philbrick-Stingel”, Whitfield writes. It is still in circulation somewhere.

The book proves as much about Whitfield as his anti-hero, but it is Philbrick who brings the pages alive. Such magnetism perhaps explains Whitfield’s enduring sympathy with Philbrick’s plight — a generosity that is hard to share. Philbrick seems anything but sorry, especially given what’s transpired since Whitfield wrote All That Glitters. At the start of this year, three years earlier than expected, Philbrick left prison on two years of supervised release. He marked this freedom on Instagram in a shared post with his girlfriend Victoria Baker-Harber, star of reality TV show Made In Chelsea; the pair were snapped on a picnic blanket with their toddler.

This happy family portrait was taken to accompany an article in Vanity Fair that gives Philbrick’s shame-free version of events. He was, he says, a novice rogue in an unregulated market of willing participants: “By no means am I blameless, but the people I was partnered with were all seeking an edge.” Perhaps this is the feature that Whitfield resisted writing.

Book cover of Token Supremacy by Zachary Small

Philbrick’s high-stakes deals were fostered within the art market’s increasingly financialised environment, with its promise of great returns despite flimsy data. During the Covid-19 pandemic, when in-person art events were nearly all cancelled, such promises morphed into a craze for digital, cryptocurrency-based, non-fungible tokens (NFTs). In Token Supremacy, journalist Zachary Small ably turns his forensic skills to the NFTs’ swift boom and bust.

Art comes across as offering a suitably shady environment. Small finds it was ripe for crypto-based speculation, partly because “it is one of the last major unregulated markets in the world”, offering “tactics that would be off-limits in traditional finance”, a recurring refrain and an environment that Philbrick says supported his schemes.

Token Supremacy tackles a jargon-heavy episode of art market history with welcome clarity and arch humour. The book is hooked on key characters, including the graphic designer turned artist Mike Winkelmann, aka Beeple, whose NFT of 5,000 daily digital images made since 2007, many of a puerile and cartoonish bent, sold for an eye-watering $69.3mn through Christie’s in 2021.

Small’s other crypto-hungry characters include Seth Goldstein, founder of New York’s Bright Moments Gallery — proof that even in a virtual world, people mostly prefer to congregate in a physical space. It opened in 2021 with mantras on the wall such as “you can’t spell culture without cult”.

Book cover of Art Auctions by Kathryn Brown

Small skilfully characterises the fine line between discretion and duplicity at the highest echelons of the art world, and has little love for the complicity of the auction houses in a frothy market. Their influence in this century is analysed further in Art Auctions by the academic Kathryn Brown, who offers a gentler look at the “theatre” of the salerooms in her slim tome. Her research into the psychology of buyers characterises the milieu that the likes of Inigo Philbrick could exploit.

A more grassroots perspective on the market’s machinations comes courtesy of another skilled journalist, Bianca Bosker, in Get the Picture, a page-turning romp around New York’s art world. Her quest, to determine what separates “good” from “bad” art, prompts her to find junior roles at art galleries, then with the artist Julie Curtiss and for the Solomon R Guggenheim Museum, all while recording her findings. These reveal many of the baffling codes around intangible value, served up through genuine laugh-out-loud moments, not least her experience of having a social media “ass influencer” sit on her face in the name of art.

Book cover of Get The Picture by Bianca Bosker

It’s not all funny, however. Emerging artists and gallerists are illustrated juggling several jobs at the same time to make ends meet, all while helping “billionaires hang their second Rothko in their third home”. The sometimes cruel treatment of employers towards their junior gallerists is also exposed. Bosker finds behaviour “that was at best morally dubious, very frequently discriminatory, and at worst potentially criminal”.

As in Whitfield’s and Small’s books, she illustrates a world of accepted white-collar crimes. In one instance, a museum trustee buys two editions of a photograph — one to go in the museum, one for her home. “A little philanthropy, a little polite corruption,” Bosker writes, noting that the museum’s stamp of approval will increase the value of the personally owned picture. A fellow gallerist sympathises with her discomfort at the situation, soon after admitting that he has never paid any sales tax.

The stories might be extreme, but there is an uncomfortable familiarity to them. The industry’s integrity seems questionable at best when it is presented as a world in which someone like Philbrick can thrive, suffer disgrace and then set the stage for a sensational comeback. Brown notes the lack of any overarching responsibility. Auction houses, for example, “have no particular commitment to the sustainable functioning of art world of their markets,” she writes. Their remit is to sell art for the highest price for their consignors.

Midway through All That Glitters, Whitfield recalls a banker-collector who neatly sums up a world in which the dictum caveat emptor has rarely been more relevant: “‘The best thing about the art market,’ he told me, ‘is that it’s completely unregulated. However,’ he continued, ‘the worst thing about the art market is that it’s unregulated.’”

The reality, though, is that if the art market wants to grow, it can’t have it both ways. Before taking money from the next generation of buyers, some of their needs will have to be met. This means embracing the increased transparency and accountability that digital natives have come to expect. Regulation might not appeal to a world of freethinking creatives, but surely its time has come.

All That Glitters: A Story of Friendship, Fraud and Fine Art by Orlando Whitfield Profile £17.99/Knopf $29, 336 pages

Token Supremacy: The Art of Finance, the Finance of Art and the Great Crypto Crash of 2022 by Zachary Small Knopf £27/$32, 368 pages

Art Auctions: Spectacle and Value in the 21st Century by Kathryn Brown Lund Humphries £19.99, 104 pages

Get The Picture: A Mind-Bending Journey Among the Inspired Artists and Obsessive Art Fiends Who Taught Me How to See by Bianca Bosker Viking $29/Atlantic £20, 384 pages

Melanie Gerlis is the FT’s art market correspondent

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