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AT STAKE A dispute could cost Annie Leibovitz the control of her work. Credit Tony Cenicola/The New York Times

IF money and fame are the yardsticks, Annie Leibovitz is one of the most successful photographers of all time. She has a seven-figure salary from Vanity Fair and commands tens of thousands of dollars a day from commercial clients like Louis Vuitton. Her latest book, “At Work,” made best-seller lists, and an exhibition of her classic images — Demi Moore naked and pregnant, Mikhail Baryshnikov on the beach — has been touring the world for over two years.

So as the news has spread in recent months that Ms. Leibovitz is facing extraordinary financial troubles, with the possibility of losing her Civil War-era town houses in Greenwich Village, a home in upstate New York and the rights to decades of her work, many have formulated the same questions: How is this possible? How could an artist of her standing be in such financial straits? If Annie Leibovitz can’t make it in New York, who can?

On July 29, Ms. Leibovitz was sued in State Supreme Court for nonpayment by a company that had lent her $24 million, and which demanded access to her homes so it could begin the process of selling them to satisfy her debt. Ms. Leibovitz had taken out the loan last year, pledging as collateral properties in Greenwich Village and in Rhinebeck, N.Y., her negatives and the rights to her photographs. The lender, Art Capital Group, claims Ms. Leibovitz is behind on hundreds of thousands of dollars in unpaid fees associated with the loans.

The photographer, 59, declined to comment. Friends and colleagues said that despite her many successes, Ms. Leibovitz has been shadowed by a long history of less than careful financial dealings. Public records show that in the last two years, Ms. Leibovitz has faced tax liens of $1.4 million and two lawsuits claiming that she has not paid more than $700,000 in bills for photography services.

“The mind that can take these extraordinary pictures is not necessarily the same mind that is a perfect money manager,” said Graydon Carter, the editor of Vanity Fair.

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A recent series of personal issues has made navigating her already complex life more difficult, close associates said. In the last five years, Ms. Leibovitz lost her father, her mother and her companion, Susan Sontag; added two children to her family and oversaw the costly and controversial renovation of three properties in Greenwich Village.

Charlie Scheips, the former director of the Condé Nast photo archive who helped Ms. Leibovitz make a deal last year with an auction house to sell prints of her photographs, said that when he spoke to her recently, he was told: “I’m really under the gun. I’ve got three daughters, I lost my spouse. I’ve got too many jobs to do and it’s chaos.”

Matthew Hiltzik, a spokesman for Ms. Leibovitz, pointed a finger at the lender suing Ms. Leibovitz, Art Capital Group, a company in New York with a history of litigation over its boutique loans to artists, art dealers and collectors, who pledge their art works as collateral. “Annie is in the same shoes as many other people involved with Art Capital,” Mr. Hiltzik said.

The firm, with offices in a former Sotheby’s building on Madison Avenue, has been compared to a high-end pawn shop, and it has sued and been sued by a litany of clients and associates, including Julian Schnabel, its former lawyers and ex-employees.

But all that would presumably have been known to Ms. Leibovitz before she turned to Art Capital in 2008 for a $22 million line of credit, which was later increased to $24 million. The full amount, plus interest and fees, is due Sept. 8, according to the lawsuit.

The question is why she found herself needing that much cash. Mr. Hiltzik said his client had no comment.

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SUBJECT Annie Leibovitz. Credit Timothy A. Clary/Agence France-Presse — Getty Images

Friends and colleagues agree that it is not a taste for luxuries that has caused Ms. Leibovitz’s financial difficulties. Although well known for extravagant spending while on assignment, those expenses are paid by her employers.

“Annie is not an expensive liver herself,” said Tina Brown, who edited Vanity Fair from 1984 to 1992, where Ms. Leibovitz began working after her early years at Rolling Stone magazine. “She hangs out with her kids. She doesn’t hang out in the lights at the parties.”

In the 1970s, Ms. Leibovitz flew around the world chronicling rock ’n’ roll during its hedonistic heyday and accompanying hard-partying reporters like Hunter S. Thompson. She was notoriously bad with her expenses and was also known to give away expensive Minox cameras to anyone who said they admired hers.

In “Life Through a Lens,” a documentary about Ms. Leibovitz directed by her sister Barbara Leibovitz, Jann Wenner, the founder of Rolling Stone, said that he thought her move to Vanity Fair in 1983 might be good for her because she was at her “peak drug use and was so irresponsible, was leaving rental cars everywhere and not turning things in on time.”

Over the years at Vanity Fair, her shoots became more complex and expensive, often elaborate as movie shoots. “Month after month, it got a little bit more complicated with every shoot,” Jane Sarkin, a Vanity Fair features editor, said in the documentary. “Her demands became bigger. Fire, rain, cars airplanes, circus animals — whatever she wanted she got.”

As Ms. Leibovitz became more famous and successful — she was hired by American Express, Gap and the Milk Board for prominent advertising campaigns— her business and personal life became more complicated.

For years, she declined to speak publicly about her relationship with Ms. Sontag,the writer 16 years her senior. David Rieff, Ms. Sontag’s son, said that the relationship between the two women, who met in 1988, was “on again and off again.”

Ms. Leibovitz purchased a penthouse apartment at the London Terrace complex in Chelsea in 1988, and from her balcony could see Ms. Sontag’s penthouse in the same complex. A photo of the view appeared in her 2006 book, “A Photographer’s Life.”

Meanwhile, she was running a studio in a garage she owned in Chelsea, where she made many of her portraits. A close business associate, who asked not to be named so as to preserve the professional relationship, said that Ms. Leibovitz has been lax about keeping records of which studio expenses to bill to which client. In a 2008 book, Ms. Leibovitz admitted of the Chelsea studio: “We had too much equipment. Things were getting out of hand.”

Ms. Leibovitz gave birth to her first child, Sarah Cameron Leibovitz, in 2001. Around the same time the photographer’s father, Samuel Leibovitz, became sick, and Ms. Sontag had a recurrence of cancer. Ms. Leibovitz spared no expense shuttling from magazine shoots in far-flung locales to hospital beds to see her father and Ms. Sontag, the business associate said.

In 2005, 37 days after the death of Ms. Sontag, Ms. Leibovitz’s father also died. Three months later, on May 12, Ms. Leibovitz’s second and third children, twins, were born. In the documentary, Ms. Leibovitz is shown crying as she holds Ms. Sontag’s photo.

There has been speculation on blogs and in news articles that Ms. Leibovitz’s financial problems arose because Ms. Sontag left her a large inheritance, with steep taxes due because the two women were unable to be legally wed.

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Her property in Greenwich Village. Credit Allen Salkin/The New York Times

But Mr. Rieff, the executor of his mother’s estate, said that all Ms. Leibovitz received from Ms. Sontag were sentimental items.

Meanwhile, Ms. Leibovitz was facing real estate expenses. She had bought two adjacent town houses in 2002 on West 11th Street for $4.15 million. During renovations, a neighbor sued her over a damaged wall. Historic preservationists picketed the renovations, holding signs saying, “Not a pretty picture.”

The neighbor withdrew the suit when Ms. Leibovitz bought his town house, her third, for $1.87 million. She lives and works in two, and rents out the third. Ms. Leibovitz has recently taken on more commercial work, shooting Keith Richards, Sofia and Francis Ford Coppola, and a group of former astronauts for Louis Vuitton ads.

A deal with the auction house Phillips de Pury to sell portfolios of some of her prints for $33,000 did not go as well as hoped, possibly because the first sale of the works took place in October 2008, just as the art market fell apart. Colleagues and close business associates of Ms. Leibovitz are of two minds about how she might escape her financial bind. Some assume her talent and earning power can bail her out. “If anybody has the ability to put these debts away through work, she has the energy and the opportunity,” Mr. Carter said. “She has an infinite capacity for work.”

But others said Ms. Leibovitz needs to reexamine her attitude and habits around money and spending.

Jerrold Mundis, who has counseled well-known people with debt issues, and does not know Ms. Leibovitz, said, “Celebrity or even a spectacular talent doesn’t proof one against a problem with debt.”

In its lawsuit, Art Capital alleges that Ms. Leibovitz was aware that her homes and intellectual property “would likely need to be sold in whole or in part” to satisfy her $24 million debt. It seeks to begin those sales before Ms. Leibovitz’s Sept. 8 deadline for full repayment.

In fact, Art Capital appears to have been shopping the rights to Ms. Leibovitz’s photographs for several months. In a separate lawsuit the lender filed in State Supreme Court this April, it charged the photo agency Getty Images with going behind its back after it had begun talks over Ms. Leibovitz’s work.

The suit states that Art Capital had been in talks with Getty over a sale of Ms. Leibovitz’s archive, valuing it at more than $50 million. Art Capital alleged it also offered Getty a chance to hire Ms. Leibovitz to take freelance assignments. The suit charged that Getty then went directly to Ms. Leibovitz and signed her for $1.1 million to do eight shoots over two years.

In March, Getty announced in a press release that Ms. Leibovitz was “available for commission photography.”

Art Capital charged that Getty’s signing of Ms. Leibovitz had made it difficult to sell her archive.

On July 31, Justice Emily Jane Goodman denied Art Capital’s request for a preliminary injunction against the contract between Ms. Leibovitz and Getty. The judge dismissed parts of the lawsuit, but ruled that other issues would be decided later.

Until now, Ms. Leibovitz has closely guarded the right to reproduce her photographs. But should she lose control of her archive, her famous portraits of Whoopi Goldberg, Jack Nicholson and the like may one day be found on postcards in Times Square.

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