If money and fame are the yardsticks, Annie Leibovitz is one of the most successful photographers of all time. She has a reported $3 million-a-year...

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If money and fame are the yardsticks, Annie Leibovitz is one of the most successful photographers of all time. She has a reported $3 million-a-year salary from Vanity Fair and commands tens of thousands of dollars a day from commercial clients such as 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 more than two years.

So as the news has spread in recent months that 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?

On Wednesday, Leibovitz was sued in state Supreme Court for nonpayment by a company that had lent her $24 million and that demanded access to her homes so it could begin selling them to satisfy her debt. 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 Leibovitz is behind on hundreds of thousands of dollars in unpaid fees associated with the loans.

Leibovitz has refused to cooperate with Art Capital’s efforts to sell her photographs and property, the suit contends. She has not allowed real-estate agents engaged by Art Capital into her homes for the purpose of appraising their value and showing them to potential buyers, according to the suit.

The photographer, 59, declined to comment. Friends and colleagues said that despite her many successes, Leibovitz has been shadowed by a long history of less-than-careful financial dealings. Public records show that in the past two years, Leibovitz has faced tax liens of $1.4 million and two lawsuits claiming 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, editor of Vanity Fair.

A recent series of personal problems has made navigating her complex life more difficult, close associates said. In the past five years, 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.

“It’s chaos”

Charlie Scheips, former director of the Condé Nast photo archive who helped 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 Leibovitz, pointed a finger at the lender suing 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,” Hiltzik said.

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

But all that would presumably have been known to 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. Hiltzik said his client had no comment.

Bad with her expenses

Friends and colleagues agree it is not a taste for luxuries that has caused 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 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, Leibovitz flew around the world chronicling rock ‘n’ roll during its hedonistic heyday and accompanying hard-partying reporters such as 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 Leibovitz directed by her sister Barbara Leibovitz, Jann Wenner, the founder of Rolling Stone, said 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 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 Sontag, the writer 16 years her senior. David Rieff, Sontag’s son, said the relationship between the two women, who met in 1988, was “on again and off again.”

Leibovitz purchased a penthouse apartment at New York’s London Terrace complex in Chelsea in 1988, and from her balcony could see Sontag’s penthouse in the same complex. 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, said Leibovitz has been lax about keeping records of which studio expenses to bill to which client. In a 2008 book, Leibovitz admitted of the Chelsea studio: “We had too much equipment. Things were getting out of hand.”

Births, deaths

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 Sontag had a recurrence of cancer. Leibovitz spared no expense shuttling from magazine shoots in far-flung locales to hospital beds to see her father and Sontag, the business associate said.

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

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

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

Meanwhile, Leibovitz was facing real-estate expenses. She bought two adjacent town houses in 2002 in Greenwich Village for $4.15 million. During renovations, a neighbor sued her over a damaged wall.

The neighbor withdrew the suit when Leibovitz bought his town house, her third, for $1.87 million. She lives and works in two, and rents out the third. She 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.

Colleagues and close business associates of 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 put these debts away though work, she has the energy and the opportunity,” Carter said. “She has an infinite capacity for work.”