It was a lovely night for a difficult meeting.

Late last October, Johnny Depp sat for dinner with two forensic accountants and his business manager of six months, Ed White, in the bucolic backyard of White’s house, in Bel Air, California. Also present was a guest from Washington, D.C., Adam Waldman, a lawyer whose clients reportedly include Angelina Jolie and Cher. Waldman recalls there were vintage wines from White’s cellar and a catered meal served by a team of waiters. But behind the pleasantries lay a disturbing topic of conversation: the condition of Depp’s finances.

Depp professed to be in shock. After all, he is paid up to $20 million a picture. How could he possibly be so strapped for cash that his former business manager, Joel Mandel, had told him it was necessary to sell major assets, such as his château on the French Riviera? Dressed in his trademark quasi-pirate attire—heavily pinned leather jacket and an assemblage of scarves, bangles, rings, and tattoos—and rolling his own smokes, Depp told Waldman, “I’m not a lawyer. I’m not an accountant. I’m not qualified to help my 15-year-old son with his math homework. . . . I’ve always trusted the people around me.”

White’s accountants claimed to have found anomalies in the handling of Depp’s finances by his former business managers, Robert and Joel Mandel, and their firm, the Management Group (TMG). These, Waldman would later charge, included late payment of income tax and disbursing nearly $10 million to “third parties [including Depp’s sister] close to or who worked for Mr. Depp, without Mr. Depp’s knowledge or authorization.” These transgressions and others caused Depp to borrow tens of millions of dollars at high interest rates, with his film residuals as collateral, according to Waldman. The charges were vigorously denied by the Mandels and TMG, which called them “fabricated and replete with demonstrably false allegations.”

“What’s the amount that Johnny has made [over the 17 years the Mandels represented him]?” Waldman asked White at the backyard dinner.

“Six hundred and fifty million dollars,” White replied. From that sum TMG had been paid 5 percent, and Depp’s attorney Jake Bloom got another 5 percent, for a total of around $65 million.

At the conclusion of the dinner, Waldman remembers Depp asking, “Will you represent me? Will you get to the bottom of this and give me some advice?”

On January 13, after Waldman had worked with White and eight additional lawyers to sift through about 24,000 e-mails, Depp’s attorneys filed a scathing lawsuit against TMG, seeking $25 million in damages for negligence, fraud, unjust enrichment, and breach of fiduciary duty, among other things. Eighteen days later, TMG responded with a blistering 31-page cross-complaint, claiming that Depp was a spendthrift of epic proportions, who, despite his manager’s constant warnings, refused to curb his “selfish, reckless, and irresponsible lifestyle.”

By 2013, Depp’s expenses had ballooned to $2 million a month, TMG claimed—a burn rate disputed by his new attorney. The Mandels’ cross-complaint describes 14 residences, including the château in France and a four-island chain in the Bahamas. There were also a 156-foot cash-guzzling yacht and 12 Los Angeles storage facilities full of memorabilia, including 70 collectible guitars, plus major artwork by Klimt, Modigliani, and Basquiat, among others. Forty full-time employees cost Depp $300,000 a month, they claimed—although Waldman says there are only 15 employees, some of them consultants. Round-the-clock security for himself, his two children, and various family members costs $150,000 a month more. In addition to the $10 million supporting friends and family, he spent $30,000 a month on wine “flown to him around the world,” the lawsuit alleges, and $5 million for a blowout memorial service for the late gonzo journalist Hunter S. Thompson, including blasting his ashes from a 153-foot custom-built cannon at Thompson’s home in Aspen. (Depp idolized Thompson and later told his attorney, “If I had $5 million and one dollar, I [still] would have done it. That was my brother.”)

Depp’s fiery, 15-month marriage to the actress Amber Heard cost himanother $7 million. Three years after meeting on the set of The Rum Diary, in which Depp played a rum-addled Hunter S. Thompson, the couple began living together. The union ended in a tabloid feast, which included a temporary restraining order and accusations of domestic abuse. Heard detailed two of Depp’s supposedly violent episodes against her in a court declaration. Soon, there were photographs in the media of her with a black eye and a bloody lip.

Depp’s team issued denials. “Amber is attempting to secure a premature financial resolution by alleging abuse,” said Depp’s lawyer Laura Wasser in a court document. Heard filed for divorce on May 23, 2016. A settlement was announced in August, a few days before the couple was due in court.

Right on the Money

Hollywood business managers are typically invisible, and the Mandels have in the past stayed below the radar. Before Depp, they had never been sued by a client, their attorney insists. William Morris Endeavor co-C.E.O. Ari Emanuel calls them “true, honest, loyal brokers who aren’t afraid to take a position with a client on what you should and shouldn’t do.” Emanuel says he has entrusted his financial life to them since he was a “baby agent.” Another longtime TMG client says, “Rob Mandel has been one of the executors of my estate for 30 years, and Joel Mandel is designated as one of my executors and trustees in the event that Rob can’t serve. That includes overseeing my kids.”

Of the various allegations by Depp’s lawyer, TMG’s attorney Michael Kump responds, “For 17 years, TMG timely filed Depp’s tax returns and, funds permitting, always timely paid Depp’s income taxes.” Any taxes paid late have “everything to do with Depp’s over-the-top spending and had nothing to do with TMG’s negligence,” he says. Regarding allegations over disbursements and loans, he says, “Over a 17-year period, TMG did not make a single distribution of Depp’s funds without authorization by Depp and/or his sister and personal manager, [Christi] Dembrowski,” and did not negotiate or dictate the terms of any high-interest loan for Johnny Depp.

Was Johnny Depp an innocent fleeced at the hands of Hollywood hucksters or a scheming artful dodger attempting to sue his way out of his wastrel lifestyle and outrageous spending and any remaining debt to his former business managers? Both sides are demanding a jury trial, currently set for January. Depp is asking for at least $25 million, while his former business managers are demanding $560,000 in damages and a court declaration that states “Depp caused his own financial waste.”

“Money doesn’t change anybody,” Johnny Depp once said. “Money reveals them. . . . I’m still exactly the guy that used to pump gas.”

He arrived in Hollywood at 19 in 1983, a guitarist in a rock ‘n’ roll band, whose fortunes soon failed. A high-school dropout and juvenile delinquent, Johnny was dead broke, living in a seedy apartment and filling out job applications at stores on Melrose before turning to telemarketing—“selling pens over the phone in order to eat,” he has said—in a sweatshop at Hollywood and Vine. His first wife, Lori Anne Allison, introduced him to actor Nicolas Cage, who “wanted to hook me up with an agent,” Depp once remembered. “You should try being an actor,” Cage advised him.

Depp was promptly cast in Wes Craven’s 1984 horror film, A Nightmare on Elm Street, then in Oliver Stone’s Oscar-winning war film, Platoon, and subsequently as an undercover cop on the TV series 21 Jump Street. But he got stuck as a “TV boy,” in his words, until a new agent, Tracey Jacobs, rescued him with an odd movie script: “It was the story of a boy with scissors for hands—an innocent outcast in suburbia,” Depp wrote. “I read the script instantly and wept like a newborn.”

Director Tim Burton’s Edward Scissorhands was a 1990 smash, and it made Depp a movie star. By 1999, having starred in three equally quirky films—What’s Eating Gilbert Grape, Ed Wood, and Don Juan DeMarco (with Marlon Brando and Faye Dunaway)—he was living large, in “Dracula’s Castle,” a vast Hollywood fantasy of turrets and towers, built in 1927, just above Sunset Boulevard.

In 1999, Depp and his sister, Christi Dembrowski, hired the Mandels, whose TMG was then 12 years old. The brothers operate a family shop: Robert is a tax attorney, and Joel is a transactional attorney, although they don’t represent their clients as attorneys, they say in court filings. Rather, they are full-service business managers, and their powerful clients rely on them for pretty much everything financial: collecting their payments from studios and other entities, paying their bills, filing and paying their taxes, balancing their books. (Dembrowski did not respond to requests for comment.)

For their first meeting, Joel, who would be the point man on Depp’s account, drove down Sunset and through the gates to the 7,430-square-foot Castle. In a scene straight out of Sunset Boulevard,he was ushered into the Gothic manse, whose walls and floors were covered with hundreds of pieces of art. Johnny, then 36, greeted him from his desk in an office filled with books, collectible guns, guitars, and memorabilia. Well read, much traveled, and intelligent, Depp was pleasant, personable, prepared, and a great listener. He had previously relied on his sister for many of his business dealings. Now Joel Mandel would take over.

In turning over his finances to a professional business manager, the actor was asked to consult with Joel Mandel before spending his hard-earned money, according to a source close to TMG. Not that anything seems to have been denied. Because, in 2003, Depp starred in the first of five Pirates of the Caribbean blockbusters, and it was his character—the mumbling, bumbling, dreadlock-and-bead-festooned Captain Jack Sparrow—that turned Pirates into box-office gold. Depp was paid $11 million for the first installment, and $20 million per sequel, with reportedly more than $40 million in back-end payments.

Spending Like a Sailor

With the studio payments flowing in to TMG, Depp developed what the firm’s cross-complaint would call “a never-ending desire to spend.” It began with a boat. After introducing Depp to acting, Nicolas Cage—who himself reportedly blew through $150 million and faced bankruptcy in 2009—showed him his style of spending. He lent him one of his two yachts, the 126-foot Sarita, and Johnny and his then partner, French actress Vanessa Paradis, and their two young children, Lily-Rose and Jack, promptly set sail. When the family disembarked onto the beaches of the Bahamas, the real-estate brokers, specialists in the ultra-rarefied clientele who can afford their own private islands, were upon him. This particular dream apparently spoke to Depp, who had visited Marlon Brando on his private South Pacific atoll, Tetiaroa, after the two had worked together on Don Juan DeMarco.

In 2004, Joel accompanied Depp on an island-shopping cruise. When they stepped off the yacht and onto the beach in the Exumas they found . . . nothing. Little Hall’s Pond Cay, a chain of four uninhabited islands 60 nautical miles southeast of Nassau, was on the market for $3.6 million. It had six sandy beaches. And no plumbing, sewage facilities, or electricity.

According to a source close to TMG, the manager focused on the cons (the exorbitant expense of creating infrastructure), while the client saw only the pros (a refuge for him and his family, a place to recharge for his next major studio picture). And when the manager couldn’t talk Depp out of the islands, he did his best to negotiate the price down to $3,225,000.

Depp’s attorney says that the Bahamas island chain and other real-estate purchases have been great investments for the actor and have appreciated many times above their acquisition costs. But if you own an island, it is mandatory also to own the ultimate spending machine: a yacht. In Depp’s case, an old-fashioned fantasy of smokestacks and masts that Captain Jack Sparrow might sail in his leisure hours. Depp found her in Turkey: Anatolia, a steam-powered replica yacht, built in 2001. The asking price was said to be $8.75 million, with $8 million more needed for refurbishment expenses.

Knowing that Mandel would suggest analyzing the math, as he always did, according to a source close to TMG, Depp dispatched his sister to insist, This is very important to Johnny, because a boat is the only place he can relax and recharge.

Fifteen minutes later, Depp called, and Mandel is said to have advised him on what he had to do work-wise to meet the huge expense of owning the yacht along with his other financial obligations: two studio pictures a year—or $40 million in guaranteed compensation.

I get it and I’m O.K. with it, Depp said, according to the source.

The yacht would have a multi-national crew of eight and operating and maintenance costs between $300,000 and $400,000 a month; Depp christened it the Vajoliroja: Va for Vanessa Paradis, jo for himself, liro for daughter Lily-Rose, and ja for son Jack. He commissioned the Malibu-based LM Pagano Design to decorate her in a style described in this magazine as “Orient Express by way of Parisian brothel.”

Back in Hollywood, the Castle must have seemed small compared with the open seas, so Depp sought to annex the cul-de-sac surrounding his home by buying all of its houses, for a total cost of around $10 million. They would serve as an art studio, a guesthouse for his mother and friends, and, the largest, a state-of-the-art recording studio.

But by 2007, Joel Mandel believed that Depp wasn’t making the annual income that he had said he would, according to the cross-complaint. The actor allegedly became aloof, hard to reach, exploding with expletives when challenged over expenses. The suit cites “hundreds of conversations”—in-person meetings, telephone calls, and e-mails—that once were friendly but devolved into “profanity-laced tirades where he [Depp] abused the professionals surrounding him and claimed that he would work harder to afford whatever new item he wanted to purchase.”

By this point, according to a source close to TMG, Depp had to earn more than $60 million a year, before taxes and agents’ commissions.

Depp’s agent, Tracey Jacobs, and her team went into overdrive to find him new projects. “It became harder and harder to find things that were good that would pay full-boat,” says an industry source. “He’s $10-million-plus and they were just not making many dramas that pay $10 million.” This led to such bombs as Transcendence, Mortdecai, and The Lone Ranger, not to mention a curious Dior Sauvage men’s-cologne commercial, for which Depp purportedly received a fee of $16.4 million. (Jacobs did not respond to requests for comment.)

By October 2012, according to the cross-complaint, the situation had become so dire that Jake Bloom and Joel held a three-hour “come to Jesus” meeting with the actor in his guitar-filled recording studio. Since Depp didn’t like reviewing lengthy financial documents, they distilled everything down to a one-page summary, but Depp didn’t want to see that either. So they walked him through the situation, telling him that “immediate action” was required.

“Depp was facing a potential, public financial crisis,” according to the cross-complaint, “which would have forced him to default on a multi-million[-dollar] loan with CNB [City National Bank].” The bank demanded payment on one $5 million loan, but “Depp did not have the funds to repay it . . . [due to his] refusal to curb his profligate spending.”

“To save Depp from a public and devastating financial collapse,” TMG lent him the $5 million to repay the loan, and he signed new loan papers with TMG, securing it with two of his Hollywood properties.

The yacht was sold in late 2013 to American buyers. Still, it wasn’t enough.

Funny Business

Mandel pleaded with Depp’s associates to give him a heads-up—an “Expense Watch,” according to a source close to TMG—on any extraordinary expenditures so that Mandel could attempt to intercede. If he couldn’t stop the purchase, perhaps he could attempt to negotiate the price.

He began getting frequent e-mails.

Los Angeles: “Johnny has purchased 10 cases of wine from 20/20 [Wine Merchants, where, the source insists, his outstanding bill once reached $1 million] . . . the total will be $290,000 + tax. Wow.”

New York: “Johnny [wandered] into Fred Leighton jewelry and spent $500,000 on a diamond cuff [and other jewelry].”

Mandel, according to a source close to TMG, discovered many purchases only after receiving the invoices, such as on September 22, 2014, when he got a call from a New York attorney saying that Depp had bought the archives of the author and former V.F. contributing editor Nick Tosches. The negotiations had supposedly taken place late one night in London’s Dorchester hotel, and the agreed-upon price for the archives was $1.2 million. (Tosches did not respond to requests for comment.)

Dubious, Mandel asked for proof. An e-mail arrived with a photograph of Dorchester stationery, on which Depp had written, “i, Johnny Depp, hereby agree to purchase the archives of Saint Nick Tosches for the sum of $1.2 million dollars. Johnny Depp.”

The agreement appeared to be sealed, beside his signature, with drops of blood.

Depp’s attorney Adam Waldman claims, “Most of these points are false, grossly misleading or bewilderingly irrelevant to the lawsuit. These questions form the basis of the Mandels’ non sequitur defense against a litany of our specific allegations. Mr. Depp’s ‘financial woes,’ as the Mandels term it, are not at issue in Depp vs. Mandel.”

The pendulum swung back on February 7, when Depp received an e-mail regarding one of TMG’s ex-employees, a woman who had worked on his account. “She knows all the dirt and all the thieves !!!!” the e-mail said.

On May 26, Depp’s attorneys succeeded in unsealing the deposition of the former TMG employee, Janine Rayburn. They say her testimony reveals that she was instructed “to commit improper acts on the Depp account.”

In their filings, TMG’s team called Rayburn a “serial liar” who lied 12 times during her deposition. She “did not have substantial responsibility on Depp’s account,” handling only “bill pay and data entry,” and she worked for TMG for only two years and only spoke to Depp for “like two seconds” at a holiday party.

Rayburn’s attorney, Grant Gelberg, responds, “Janine Rayburn has worked in business management for over 30 years. She is beloved by her clients and works tirelessly for them. She had a legal obligation to appear at her deposition in the Johnny Depp v. TMG case and she truthfully answered all questions that were put to her.”

On June 19, in a court motion, TMG’s attorneys released a batch of e-mails, including a late-2009 e-mail from Depp to Joel Mandel that suggests the actor understood his urgent need to raise more cash: “know that i will be starting THE TOURIST, on or about the 15th of february, which will be 20 mil. i will then go, virtually, straight into PIRATES 4, for 35 mil and then in turn to DARK SHADOWS for another 20 mil . . . what else can I do??? you want me to sell some art??? i will. you want me to sell something else??? sure . . . what??? . . . i got bikes, cars, property, books, paintings and some semblance of a soul left. where would you like me to start??? i don’t like being in this situation, but there wasn’t a whole lot of choice, as THE RUM DIARY was a sacrifice we knew would be happening and the last proper paycheck was PUBLIC ENEMIES. i will do my best, joel.”

Waldman responds, “Which of the allegations in Mr. Depp’s complaint do those e-mails serve as a defense against?”

Meanwhile, reports of hard partying and being chronically late to the set came out of Australia, where Depp was filming Pirates of the Caribbean: Dead Men Tell No Tales, the fifth installment in the series. Two directors of Depp’s recent films came to his defense, however. “The Johnny I worked with so closely, the Johnny I admire, isn’t the Johnny that’s been portrayed,” says Scott Cooper, who directed Depp as the psychopathic mobster Whitey Bulger in Black Mass. “Professionally, he was on time, word-perfect, and polite to all,” says Sir Kenneth Branagh, who acted with and directed him in the upcoming Murder on the Orient Express.

“He’s a gentle soul, and it’s hard to see him in any other light,” says Jerry Bruckheimer, producer of the Pirates franchise.

Despite a critical drubbing, the latest Pirates turned out to be a box-office smash, raking in $271 million globally on its Memorial Day weekend opening. The film, which cost a reported $230 million to make, is on course to bring in more than a billion dollars to Disney.

Regardless of the legal wrangling yet to come, Johnny Depp will live to shop another day.