For starters, 'She said she would like to make more money,' recalled Fifth Avenue gallery owner Edwynn Houk, who devised the plan with her before she took it to an auction house that staged a London exhibition in 2008 with even higher prices for the jumbo photos -- $33,000. But beyond the bottom line, Leibovitz was intent on solidifying the status of her photos as fine art, Houk said. At those prices, buyers would have to be interested in more than the celebrities: 'They were collecting the work of Annie Leibovitz.' That Leibovitz wanted to control how her work is positioned is hardly a surprise. She's the master of the setup shot, the conceptual cover -- meticulously positioning her subjects, whether it's a nude John Lennon wrapped around his wife, Yoko Ono, or Demi Moore, nude and pregnant, Steve Martin as part of a Franz Kline painting, or heads of state such as President Bill Clinton, whom she tried in vain to talk into posing while smoking a cigar in the Oval Office. That's how she's come to define modern celebrity portrait photography during her decades shooting magazine cover photos for Rolling Stone, Vanity Fair and Vogue. But Leibovitz, 59, soon could lose control of her life's work for the very reason she needed money, and fast. Leibovitz faces a Tuesday deadline to repay a $24 million loan from a New York art-finance company. Art Capital Group advanced her that sum in 2008 after the photographer, in 'dire financial condition,' as court papers put it, posted as collateral basically everything she owns -- not only her two homes but 'every photographic image ever taken by Ms. Leibovitz,' according to the lender. She isn't the first creative person to mortgage intellectual property. Lennon and fellow Beatle Paul McCartney dealt their song publishing rights and pop star Michael Jackson, who bought them, later used their catalog, and his own hits, to secure more than $200 million in loans. Representatives of singer David Bowie reaped $55 million for him in 1997 by turning the revenue stream from his old songs and recording masters into bonds -- 'Bowie Bonds,' they're called. Meanwhile, art collectors, galleries and artists themselves have embraced ways short of selling to convert the framed beauty on their walls into liquidity. Artist-director Julian Schnabel used a Picasso he owned for 20 years to secure financing to develop top-of-the-line condos in Greenwich Village. Even the esteemed Metropolitan Opera, in essence, hocked the Chagall murals in the lobby at Lincoln Center, using them as collateral for a $35 million loan. But Leibovitz's deal with Art Capital goes well beyond such arrangements. It could result in the outright sale of her photo copyrights to a party who might decide it's better to market her images in lots of 1,000, or on postcards, not the fine-art limited-edition approach she has embraced. Art Capital says it secured one more thing for its largesse -- the 'irrevocable right' to serve as her exclusive agent through the loan period and two years after, meaning it would negotiate photo shoots she does outside her contracted ones for Vanity Fair and get a cut of her newly created work too. Leibovitz signed the deal with 'sophisticated counsel,' the company says in a lawsuit, but which she since has tried to sabotage, notably by entering a separate representation arrangement with the photo agency Getty Images, which was going to pay her $1.1 million for eight assignments. That generated another suit by Art Capital, against Getty. The litigation has placed a spotlight on the pressures facing the photographer, who is juggling multimillion-dollar mortgages on her triple town house-studio in Greenwich Village and her 200-acre Astor Barns country estate up the Hudson River, and more than $2 million in tax liens and unpaid bills. Leibovitz is not talking, but supporters say she did not realize what she was signing away; like many creative sorts, she is less than focused on pocketbook matters. 'Artists like her generally don't do it for the money,' said Vanity Fair editor Graydon Carter. 'If they did they'd be working for AIG.' Those close to Leibovitz say it's not like her to relinquish authority over how the world sees the images she orchestrates, whether Whoopi Goldberg posed in a tub of milk or Chris Rock in white face. 'Annie is the most successful artist in the history of photography,' Carter said. 'That does not happen by accident. And she is nothing if not controlling when it comes to her work.' Experts in marketing intellectual property see no close precedent to the Leibovitz deal because of how it combines as collateral her real property and intellectual property, not to mention her future work. The pioneering deals crafted for music figures such as Bowie and soul legend James Brown covered only past work, not new albums or tours -- and Brown, for one, was careful to maintain control over how his songs were used, ruling out commercials for alcohol. With music figures, recordings and music publishing had a long pattern of generating income, so a cash flow could be projected for coming years. That was used to calculate the lump-sum payouts, $30 million in Brown's case, raised through bonds created by Wharton business school graduate David Pullman. In Bowie's case, several factors -- including estate planning to benefit his heirs -- prompted him to 'securitize' future royalties from the 24 albums he had released by 1997, according to his business manager, Bill Zysblat. Zysblat, who also represents Sting, crafted a similar deal for a record label that wanted to turn future income from master recordings into immediate funds to sign new artists. But, Zysblat said, 'we've never done a deal with someone who was desperate for money.' Leibovitz reached that state during a wrenching decade during which she lost both her parents and her leukemia-stricken companion, Susan Sontag. Leibovitz became a single mother of three daughters, the last two, twins, born to a surrogate. She also bought the West Village properties that proved a migraine headache even by New York fixer-upper standards. She paid $4.15 million in 2002 for two adjoining red-brick houses dating from the 1830s that she was going to transform into 9,000 square feet of living and studio space. Then a wall sagged as contractors expanded a cramped basement, leading to a $15 million lawsuit by neighbors and stoppage of work for a year. Leibovitz eventually purchased the neighbors' town home as well. Despite Leibovitz's salary from Conde Nast, her work on ad campaigns for the likes of American Express and her book and photo sales, she was looking at mounting debts, IRS tax liens and lawsuits by a lighting company and stylist. Friends insisted she was not so much a spendthrift as generous, paying an aging maid merely to cook breakfast. 'She's a person about her work and her family. ... It's not the money,' said sister Paula Leibovitz, a lawyer in the San Francisco Bay Area. A documentary by another sister, Barbara, 'Annie Leibovitz Life Through a Lens,' points out that Annie was rewarded for ignoring budgets on the job, and ordering up fire, rain or circus animals for her high-concept shoots. 'I can't say that photographing celebrities didn't change my sister's viewpoint,' mused a third sister, artist Susan Leibovitz Steinman, in the documentary. 'You do start to think you're living that life,' said Annie Leibovitz herself. Art Capital disdains suggestions it is a 'high-end pawnshop.' Spokesman Montieth Illingworth says the company is 'an art market financier' more comfortable than traditional lenders with accepting art as collateral. According to its complaint filed July 29 in New York State Supreme Court, Leibovitz approached the company in June 2008, and was granted $22 million in credit, from which she initially drew $5 million. In December, the credit line was increased to $24 million, with a lower interest rate, and Leibovitz took the entire sum. That's when the company insisted on serving as her exclusive agent, with its commissions increasing -- to 25 percent (including costs) on sale of her photo copyrights -- if she defaulted on the loan. With the clock ticking toward her Tuesday deadline to repay the $24 million, plus interest, there are a few notes of cautious optimism. Attorneys for Leibovitz just this week obtained more time, until Oct. 1, to reply to the Art Capital lawsuit, although the deadline to repay still applies. 'They're having discussions ... to resolve things,' said Leibovitz's spokesman, Matthew Hiltzik. Zysblat said financiers normally lend, at most, half the real worth of assets such as Leibovitz's, meaning her photos and homes could bring in $50 million or more. 'She's doing OK,' he said. 'She's not worried about eating,' agreed Pullman. He is a fan of Leibovitz, counting her surreal shot of rocker David Byrne, in a jacket made of leaves, as his first art purchase. Pullman views her as the rare photographer with potential to create an income stream through mass licensing, in the manner of 1960s pop art sensations Peter Max or Andy Warhol, provided the people she photographed assent to seeing their images on scarves or ties. But Carter says Vanity Fair's star photographer has more high-brow role models. 'She said recently that photographers never retire. She mentioned Steichen and Cartier-Bresson, who worked into their 90s. And Irving Penn, over 90, who's still working.' So if Carter was pondering a story on her, what sort of cover photo -- of herself -- might she suggest? Well, it's not Annie Leibovitz naked, with a barrel around her, in front of those money-eating town houses. Think grand, even by martyr standards. 'I can see her posing,' he said, 'as Joan of Arc or Saint Sebastian.' 