Inigo Philbrick probably didn’t set out to become one of the art world’s great enigmas when, at the age of 24, he opened a gallery and consultancy in London, with the financial assistance of one of the industry’s better known dealers.

Had elusiveness been Mr. Philbrick’s original intent, he would not likely have gotten himself a house account at Cipriani in London, so he could show his dinner companions that he was too important to pull out a credit card. He also would not likely have made a habit of dropping anecdotes about his most powerful clients into conversations.

Nor would he have picked VistaJet, the private airplane charter, as his preferred mode of transportation; gotten himself a $58,000 sports watch; or shacked up with a British reality TV personality named Victoria Baker-Harber, shortly after his partner Francisca Mancini gave birth to his daughter.

Not if what he really wanted was to be seen nowhere but talked about everywhere.

Yet that is what happened in the fall of 2019: a vanishing act.

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A Promising Portrait of Picasso

Before the drama began, Mr. Philbrick’s gallery had been on a prime block in the Mayfair district. It dealt artwork by Wade Guyton, Christopher Wool, Mark Bradford and Rudolf Stingel, but Mr. Philbrick’s job wasn’t guiding those artists’ careers or debuting their latest works.

Instead, he operated as a reseller, becoming one of a select number of dealers whose companies sold art not just to individual collectors, but also to groups of them.

The way this works is that clients (sometimes referred to in the trade as “specullectors”) buy ownership stakes in things like Yayoi Kusama’s “Infinity Mirror Rooms” and stainless-steel Donald Judd sculptures.

While these investors often have title to the works and occasionally even buy them in their entirety, they do not typically keep them in their homes or offices. The idea is transparently about resale: art collecting as stock investing. Money is earned on the flip, with the potential for risk differing from the stock market in important ways.

First, it is hard to verify the prices secondary market dealers pay to acquire and sell works on behalf of multiple investors. That enables these dealers to lie about prices, overcharge clients and skim off the top. Second, when a work is acquired and placed in storage, little assurance exists besides a dealer’s reputation that a 50 percent share in a painting is actually a 50 percent share.

Such was the case with a photorealistic painting of Pablo Picasso by Rudolf Stingel that Mr. Philbrick bought for $6.7 million from the Neal Meltzer gallery in January 2016, with Satfinance, a company headed by his friend Sasha Pesko.

Mr. Philbrick was sure it was a great buy.

He said as much in emails to clients that were reviewed by The New York Times. And he became particularly bullish in 2017 when a different painting by Mr. Stingel, of the artist Sam Samore, sold at Christie’s for $10.55 million, a record for Mr. Stingel.

But Mr. Philbrick spent two years searching unsuccessfully for a buyer willing to pay a considerable premium for the Picasso portrait in a private sale. When this painting took its own turn at Christie’s in 2019, the so-called hammer price (the price before taxes and fees to the auctioneer) wound up being just $5.5 million.

After that, things fell apart.

It turned out there were three parties expecting payment, one professing to own the entire painting, the other two sharing it by half. It appeared Mr. Philbrick had double-sold the work.

Ownership disputes subsequently arose over a 2006 painting by Mr. Guyton, “Flaming U,” and a 2018 “Infinity Net” work by Ms. Kusama.

Before long, many industry colleagues came to the same conclusion as Judd Grossman, an attorney representing some of Mr. Philbrick’s former clients. “It was a Ponzi-like scheme,” he said in an interview: selling one artwork more than once to get the funds to pay for another.

Although a British court has frozen Mr. Philbrick’s assets, and numerous former clients have filed lawsuits in London, Miami and New York, Mr. Philbrick has not been charged with a crime. He did not respond to emails and messages sent to his Instagram account. Calls to his cellphone rang until they didn’t.

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New Kid on the Auction Block

“It’s very fashionable when someone does something wrong to say, ‘I always knew he was a criminal,” said Kenny Schachter, an artist, gadfly and columnist for Artnet. “I recently walked into one gallery and somebody tells me, ‘I knew from the beginning.’ I was like, ‘What about this deal you did with him? What about that deal you did with him?’ I’m not ashamed to admit I liked him. He was a little arrogant and he thought he knew better than everybody else, but in certain respects he did.”

Mr. Philbrick, now 32, also had provenance of his own.

His father, Harry Philbrick. is the respected former director of the Aldrich Contemporary Art Museum in Ridgefield, Conn., near where Inigo grew up. His mother, Jane, is a Harvard-educated writer and artist who teaches at Parsons School of Design.

After high school, Inigo matriculated at Goldsmith’s, University of London, a prestigious art school whose graduates include his father and the British dealer Jay Jopling.

In 2010, Mr. Philbrick got an internship at Mr. Jopling’s London gallery, White Cube. Within a year, Mr. Philbrick had become its director of secondary market sales.

It was rare to see someone rise that far so quickly, but Mr. Philbrick was spry, attractive and eager for action.

In 2013, he opened the Inigo Philbrick Gallery with seed money from Mr. Jopling. Its mission was art speculation. Its namesake was flashy.

He got himself a flat in Mayfair and filled his closet with $7,000 Kiton suits. He showed up to auctions and bid with Gagosian-like confidence for works by Tauba Auerbach and Andreas Gursky.

In text messages shared by former clients with The Times, Mr. Philbrick bragged about his Gio Ponti furniture and his hulking 5990 Patek Phillipe Nautilus, which left him no longer in need of his previously purchased status watch. “Going to sell the Rolex,” he wrote.

But even as he hustled to make sales, he gained a reputation for not being overly aggressive with individual clients. And he knew the Stingel and Guyton catalogs backward and forward, which earned him capital, particularly with art world players who had not yet realized their grandest ambitions.

One such player was Athena Art Finance Corp, an art lending business that was started in 2015 with backing from the Carlyle Group, a private equity firm.

In 2017, Athena lent two companies Mr. Philbrick controlled $10 million. A year later, it added $3.5 million.

A second player was Phillips, the auction house, always trying to gain on the better-known Christie’s and Sotheby’s.

Mr. Philbrick did what several associates said was a considerable amount of business with Phillips. Its co-owner, the Russian business magnate Leonid Friedland, became a personal client.

When Mr. Philbrick acquired “Humidity,” a Jean-Michel Basquiat acrylic, oil and photocopy collage painting, for $12.5 million through a private sale, the seller was Phillips. When Mr. Philbrick’s clients accused him of fleecing them in 2019, the Basquiat painting was among the works in dispute.

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‘Stress About Money’

Mr. Pesko, a dashing British financier who’d dated the supermodel Natalia Vodianova, was one of Mr. Philbrick’s bigger clients. For a while, Mr. Pesko and his company Satfinance did well investing with Mr. Philbrick. In 2016, the two teamed up to buy the Stingel Picasso, with Satfinance putting in $3.35 million.

But Satfinance wasn’t Mr. Philbrick’s first investor. Before Mr. Philbrick even signed the papers to acquire the piece, there was another partner with a substantial share.

Fine Art Partners was a German company controlled by Daniel Tumpel, a former Morgan Stanley banker, and Loretta Wurtenberger, an art collector. A November 2015 contract describes them agreeing to pay $2.485 million for a stake in what Mr. Philbrick said was a $7.1 million purchase. This was $400,000 above the actual price tag.

In addition, Fine Art Partners invested millions of dollars with him on Donald Judds, Christopher Wools, a second Stingel, a Wade Guyton and a Kusama.

But the market for Guytons, Wools and Stingels declined considerably over the next two years. Mr. Philbrick kept saying to Mr. Tumpel that a giant sale was right around the corner. All the while, his footprint grew.

He opened a Miami outpost of his gallery, rented villas in Ibiza and became an expert in Barolo wine.

By January 2019, Fine Art Partners was pressuring him. It wanted results.

Mr. Philbrick repeatedly said he was inches away from a number of big deals and blamed his “stress about money” on Mr. Friedland, the owner of Phillips, whom he claimed was delinquent on payments to him for other works.

In an email to Mr. Tumpel dated Feb. 23, 2019, Mr. Philbrick described Mr. Friedland as “one of my most consistent clients, but also certainly the most frustrating.”

A month later, Mr. Philbrick told Mr. Tumpel that payment from Mr. Friedland still hadn’t arrived.

“He’s now four months late,” Mr. Philbrick wrote of Mr. Friedland, who did not respond to questions about his relationship with Mr. Philbrick and the contents of these emails. “There is an element of ‘volatile Russian’ to his affairs that I don’t always have clarity on. It’s not like working with Christie’s — but then, Christie’s wouldn’t have made this purchase!”

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A ‘Strange Sale’

One thing Christie’s was enthusiastic about selling, according to Mr. Philbrick, was the Stingel portrait of Picasso. It could, “completely reset the Stingel market,” Mr. Philbrick wrote to Mr. Tumpel in February 2019.

Even better, he produced for Mr. Tumpel documents from Christie’s showing that there was a guarantee on the painting of $9 million. If it fetched less than that amount, during the upcoming spring auction, Christie’s would pay the remaining balance—which the auction house and its competitors sometimes do when jockeying against one another to sell highly desirable works.

Then the hammer fell at $5.5 million. Mr. Tumpel asked Mr. Philbrick what had happened. Mr. Philbrick said it had merely been a “strange sale” but assured him Christie’s had made a guarantee and that the auction house was contractually bound to kick in the remaining $3.5 million.

“They were talking to me about a hammer price in excess of $10 million but one party flaked,” he said, before promising that profits where nevertheless on the way.

But the summer came and went. Fine Art Partners received no check for the sale. Moreover, there were numerous other works Mr. Philbrick had been assigned to sell for Fine Art Partners and hadn’t.

Mr. Philbrick swore it was all good.

A buyer for a Christopher Wool painting Mr. Tumpel had invested in was “coming in a few days,” Mr. Philbrick wrote in an email to Mr. Tumpel. Someone else was about to “view” the Donald Judd sculpture, but it simply was “not an artwork that will sell itself from a storage facility.” A Kusama was about to be included in a major exhibition. “As part of this,” Mr. Philbrick wrote, “we have already confirmed events with top clients of Van Cleef & Arpels and Louis Vuitton.”

But Mr. Tumpel no longer trusted Mr. Philbrick, so he contacted Christie’s to inquire about payments for the Stingel sale. He wrote that he “could not exclude the possibility that Inigo is behaving in a criminal manner.”

Soon, Mr. Tumpel received an email from Jason Pollack, the general counsel of Christie’s, who had looked at the document about the guarantee and determined, as later filed in court papers, that it was likely “falsified.”

Mr. Pollack added that although Mr. Philbrick served as an intermediary on the sale, the consignor to whom money was owed was Guzzini Partners, an art investment company controlled by Lisa Reuben, a former specialist from the Sotheby’s contemporary art department and a member of one of the richest families in Britain.

A contract between Guzzini and Mr. Philbrick from 2017 showed that Guzzini paid Mr. Philbrick $6 million as part of a package deal for the Stingel, a Guyton and a Christopher Wool painting.

Other odd details emerged about the sale.

The winning paddle was held by Stellan Holm, an Upper East Side dealer who was bidding for Mr. Philbrick on behalf of Mr. Pesko, the British financier whose company Satfinance split the cost with Mr. Philbrick to buy the painting in the first place, in 2016.

Why would he be competing to win an auction for a work he claimed to own half of?

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Following the Money

Five months after the Christie’s sale took place, Mr. Pesko and Ms. Reuben met in London for coffee. Payments on the Stingel had fallen behind.

Mr. Pesko’s explanation (later made in court documents filed on Satfinance’s behalf) was that since May, he’d paid Mr. Philbrick two installments totaling $3.35 million, which were to be paid to Christie’s. This, Mr. Pesko said, was the full amount he owed. Mr. Philbrick was the one on the line for the rest. He’d wanted to buy back the painting, because Mr. Philbrick wasn’t doing a good job selling it, and $6 million had seemed like a good price.

The problem was that Stellan Holm, as the holder of the paddle, paid under $2.35 million to Christie’s. The remaining $1 million from Mr. Pesko had not gone to Christie’s; nor had the more than $3 million Mr. Philbrick presumably owed the auction house on Mr. Pesko’s behalf, once buyer’s fees and taxes were added to the $5.5 million hammer price.

Mr. Pesko was simultaneously confronting another problem.

In 2016, he and Satfinance had provided Mr. Philbrick with an even bigger chunk of money for the acquisition of “Humidity,” the 1982 Basquiat.

That became the subject of a suit that lawyers for Mr. Pesko filed against Mr. Philbrick in London’s High Court of Justice on Oct. 22, 2019.

Its central allegations were that Mr. Pesko paid Mr. Philbrick $12.2 million for a large share and that Mr. Philbrick lied about the price, saying it was $18.5 million and that he had contributed $6 million, when it really cost $12.5 million.

Given that no more than $300,000 came from Mr. Philbrick, Mr. Pesko was likely its rightful owner. But Mr. Pesko’s efforts to recover it were failing, because Mr. Philbrick had pledged the work to Athena, the art lender, as part of the collateral for his $13.5 million (plus interest) loan.

Now that Mr. Philbrick had defaulted, Athena was refusing to release the painting.

Pointing Fingers

Andre Sakhai was the godfather of Mr. Philbrick’s daughter. The same day Christie’s sold the Stingel, Mr. Sakhai orchestrated a deal of his own, acquiring one of Yayoi Kusama’s abstract “Infinity Net” paintings from the Victoria Miro Gallery in London.

A contract between Mr. Sakhai and the gallery shows that the purchase price was $850,000. The painting was sent to New York to be stored at Uovo, one of the art world’s premier storage facilities. There, an inspection revealed that there’d been some loss to the paint because of the way it was packed and shipped, emails show. Someone would need to be hired to work on it.

According to legal documents later filed on behalf of Mr. Sakhai, he tried to hire a conservator who frequently works on Kusamas, but the person was unavailable.

Mr. Philbrick had some sway with the conservator, so Mr. Sakhai turned to him for help—hoping, essentially, to jump the line. The documents then describe Mr. Philbrick saying this would be no problem. Mr. Sakhai, he said, should simply authorize an internal transfer of the painting at Uovo, moving it to Mr. Philbrick’s room.

So Mr. Sakhai did. Soon after, Mr. Philbrick sold the painting to Parfinim, a foreign company controlled by the collector Dirk Cavens.

According to Mr. Sakhai, Mr. Philbrick had no right to sell the work without his permission, never told him he had, and didn’t pay him any money for it.

By November, Fine Art Partners had filed two suits against Mr. Philbrick in Miami.

A date was scheduled for Mr. Philbrick to appear in court with his lawyer. He didn’t show up. The lawyer representing him filed a motion to quit the case. A reporter for The Miami New Times went to Mr. Philbrick’s gallery in the design district and found the doors locked.

Through the windows, it was clear that the walls were bare. All that remained were a few swivel desk chairs, a crate and a sign on the door that said the gallery was closed for a “show change.”

Two phone numbers were listed on it for Mr. Philbrick, according to The New Times. Both were disconnected.

As Mr. Philbrick’s associates became convinced there was little chance of recovering their money directly from him, they looked for other ways to be made whole. So they started suing each other.

Parfinim, one of two purchasers of the Kusama painting, sued Uovo, the storage facility, for refusing to deliver it until his dispute with Mr. Sakhai was worked out.

Guzzini sued the actual Stingel painting “in rem,” a legal term of liability that effectively amounts to claiming ownership over other interested parties: in this case Satfinance and Fine Art Partners.

And Guzzini tussled with Mr. Sakhai’s company over who had title to a Guyton painting known as “Flaming U.” Mr. Sakhai had a stake in it, but Guzzini was in possession of it.

For a time.

In February, Guzzini’s lawyers appeared before a New York State Supreme Court judge and said it was no longer in Guzzini’s possession. The company had sold it two months before.

‘Seven Years of My Life’

On March 5, previews were taking place at the annual Armory Show, one of the art market’s larger annual fairs. The mood was subdued inside the hangar-like exhibition space on the West Side Highway. Coronavirus fears were in the air, but dealers were animatedly gossiping about Mr. Philbrick.

Michael Rosenfeld, who owns a gallery in Chelsea, described buying a Ken Price sculpture in November 2019 from Phillips for about $85,000. On collection day, he said, a person at the auction house emailed to say the Price was being held temporarily because of issues with the title, and that this was possibly related to matters involving Mr. Philbrick.

“I told them to give me my money back, which they did,” Mr. Rosenfeld said, looking at the exchange on his iPhone. (Phillips said it could not comment on the matter, citing client confidentiality.)

Several yards away, another dealer, who didn’t want to be identified, described the relief he now feels for having passed on the opportunity to work with Mr. Philbrick on the sale of a Basquiat portrait.

As the dealer told it, there was nothing suspicious about Mr. Philbrick back then. The only reason they didn’t team up was that Mr. Philbrick and the dealer disagreed about its worth.

Darting here, there and everywhere was Mr. Schacter, who, before things unraveled, repeatedly championed Mr. Philbrick in his Artnet columns.

Mr. Schacter wore a blue mountain vest, Adidas track pants and sneakers with fire engine red laces. He looked like the fourth member of the Beastie Boys, and was greeted by gallery owners and artists like royalty.

The first thing Mr. Schacter told me was that he wasn’t going to talk about Mr. Philbrick. “I just finished a 6,300-word piece on him for New York magazine,” he said.

But Mr. Schacter couldn’t help himself. He is both compulsively forthcoming and bitter about how things went down with Mr. Philbrick.

He’d plugged Mr. Philbrick repeatedly in his column and gone on vacations with him. “It was seven years of my life,” he said.

What remained now, he said, was a $1.7 million loss from a disastrous art investment they’d made together, along with a recent article in Art News that Mr. Schacter said threw him under the bus for helping to legitimize Mr. Philbrick.

Mr. Schacter still believes that his former associate had no master plan to cheat people. “In no way is it possible that he had a criminal enterprise planned from the beginning,” he said.

Instead, Mr. Schacter posited that Mr. Philbrick got overleveraged and resorted to fraud, seeking to maintain his lifestyle.

During the reporting of the story for New York magazine, Mr. Schacter said, he direct messaged repeatedly with Mr. Philbrick. Mr. Philbrick, he said, talked to him over Instagram, using alias accounts. His old account had gone private.

According to Mr. Schacter, made nothing easy, including the fact-checking.

“He’s already denied taking private planes,” Mr. Schacter said. “I was like, ‘I was on these planes with you. What do you mean you didn’t take private planes?’” (The Times spoke with another friend of Mr. Philbrick’s who described VistaJet as “Inigo’s very own sybaritic pleasure vehicle.”)

“I said, ‘You’re like ‘The Talented Mr. Ripley,’” Mr. Schacter continued. “He wrote back, ‘Google how the movie ended.’”

So Mr. Schacter did. It turns out Ripley strangles the person who is about to expose him.

Mr. Schacter said he never seriously considering suing Mr. Philbrick. “I’m not going to waste another nickel,” he said. “I won’t get it back.”

But Mr. Schacter did have a plan to mint money from his own misfortune. “I’m going to write a screenplay,” he said. “It’ll make a great movie.”