In late September, a cabal of luminaries gathered at the Museum of Modern Art Education Center in Manhattan for a two-day gabfest. It was the Louise Blouin Foundation’s annual Creative Leadership Summit, a sort of mini-Davos that encapsulates the raison d’être of the foundation’s namesake, Louise T. Blouin. The first day concluded with a black-tie reception at Blouin’s Charles Street penthouse, but really, the summit was all about making the world a better place, and its lineup was quixotic and lofty: Wikipedia founder Jimmy Wales on democracy and technology, Financial Times U.S. managing editor Gillian Tett on the future of the Eurozone and so on.

“Innovation, Creativity and Change” was the theme, according to a description for Blouin’s address, which noted, “… innovation and creative leadership can be applied to pressing global challenges. These challenges include not only the mitigation of destructive forces, such as war, poverty or security threats, but also the reinvigoration of positive practices that enable nations, communities, organizations and businesses to thrive.”

Lending a touch of irony to the confab—but absent from the agenda—was the fact that Blouin’s business, by all appearances, is anything but thriving. In fact, after years of troubles, Louise Blouin Media seems to be at a breaking point. The company has faced rounds of layoffs and lawsuits alleging non-payment, as well as speculation over when, not if, it will self-destruct completely.

An arts-focused publisher lugging around more baggage than a Louis Vuitton boutique, Louise Blouin Media is wholly owned by its proprietor. The company was created in 2003 with Blouin’s acquisition of Art & Auction (soon renamed Art + Auction). The French-Canadian multimillionaire has since expanded into a collection of print titles and international websites; she’s nothing if not ambitious. “You need to be five times better than the New York Times in terms of volume,” she once advised employees, referring to performing-arts content.

To hear Blouin tell it, she doesn’t buy and launch art publications and organize boldface conferences for the sake of it. “I have everything I want in my life,” she said back in 2005. “I do this to make a difference.”

Blouin’s stable of magazines includes Art + Auction and Modern Painters.

Difference or none, it wasn’t long before people were saying Louise Blouin Media wasn’t paying its bills. More than 10 years on, the company is said to be at a place where the lights could go out and the phones might not work. And Blouin—never mind her aristocratic mien, her reported $600 million net worth, her lavish properties in Manhattan, Southampton and London—seems a case study in how to become a formidable businesswoman and society maven while still ending up a punch line.

Slim and blonde with a soft voice known to deliver monologues equally assertive and meandering, Blouin rose from the Montreal convent where she spent her upper-middle-class adolescence to the top of a near-billion-dollar classified publishing company she co-founded in 1987 with her second husband, John MacBain, and which she later cashed out on for a reported $250 million.

Her foray into the art world began in the early 2000s with a short-lived relationship—allegedly more than just business—with the auctioneer Simon de Pury. Having relocated to London, where the tabloids feasted on her rumored fling with Prince Andrew, Blouin set out on what was said to be a $500 million mission to build up her publishing empire and its affiliated philanthropic arm. Her persona, described in 2004 by Britain’s Telegraph, was that of a “future George Soros of the art world.”

Two years later, when she was moving Blouin Media to New York, where she had dropped $20 million on that Richard Meier–designed penthouse (at press time on the market for $40 million), Blouin seemed poised to become a patron saint of high culture. Though stern, she’s not unpleasant to be around, according to people who have worked for her, and she’s possessed of a magnetism that made her an object of fascination from Notting Hill to the Upper East Side. “Everybody is talking about her,” the New York Observer declared around the time of the company’s transatlantic move, while New York magazine described Blouin’s Manhattan society debut as “gutsy, ruthless and frivolous.”

Cracks in the facade were beginning to show by the mid-aughts. There were reports of unpaid bills, salary cuts and a revolving door of disillusioned employees. In 2006, Blouin shuttered the magazine Spoon, which she’d only recently acquired. In 2008, Blouin Media’s two-year-old Culture + Travel also folded. (In addition to Art + Auction, Blouin Artinfo.com and its international verticals, the company’s remaining assets include Modern Painters, Blouin Lifestyle, Blouin Gallery Guide and the Blouin Art Sales Index.)

In early 2013, Blouin Media handed down pink slips following a global web expansion which had involved “a level of investment that was kind of astonishing,” as one former employee put it. There have been layoffs every year for at least the past five years, according to a company insider, who estimated that more than 100 staffers have voluntarily come and gone during that same period, adding, “She takes it really personally when someone quits. It’s kind of like a breakup.”

Blouin is fiercely private, and her company’s losses are difficult to confirm. But Blouin Media has been known to bleed millions of dollars a year, according to sources familiar with the books. Of roughly 200 employees who were listed on the payroll during the first half of 2013, salaries ranged from $28,000 for an assistant up to $330,000 for president Ben Hartley, who resigned the following February. During 2012, the monthly editorial budget for a group of foreign sites was at least $60,000, a former employee says—a large amount for any media venture.

Guests at Blouin’s 2011 Creative Leadership Summit enjoyed a swanky evening at Manhattan’s Metropolitan Club.

With much of her wealth said to be in non-liquid assets, Blouin has lately been selling off personal property. She also downsized Louise Blouin Media’s headquarters in 2014, relocating from an upscale West Side office to a smaller space downtown. When employees moved to the new digs, many were sequestered in a windowless basement that flooded come summer.

What’s more, a number of legal challenges have been mounted. The New York State court system lists 25 cases against Blouin or her company since 2007, 12 of which are labeled as active. In one of the latest suits, filed in February 2014, two former executives, Catherine Shanley and Wendy Buckley, allege they are owed $137,431.32 and $90,025.65, respectively. Blouin hit back in a counterclaim saying the duo undersold ads and bartered with buyers for special perks, an allegation their attorney has dismissed. In September, the Fortune 500 printing titan R.R. Donnelley reportedly slapped Blouin with a suit seeking payment on an unpaid tab in excess of $1 million. There’s been wage rage outside the courtroom as well. In 2010, nearly two-dozen writers demanded almost $18,000 worth of back pay under the acronym WAAANKAA (Writers Angry At Artinfo Not Kidding Around Anymore). This past August, a group of foreign contract writers calling themselves “Victims of Louise Blouin in India” launched their own PR campaign.

“It was always an ordeal getting paid,” says J. Hoberman, the veteran film critic, who was recruited to write for Artinfo.com on a contract basis. “It was so arduous, every single month.” (Hoberman left after about a year for a more reliable paycheck as a Times columnist.)

The past year has been particularly trying. So frequent were Blouin’s unflattering cameos in the New York Post in 2014 that her sobriquet, “The Red Queen” (a play on her wardrobe), has taken on a life of its own.

“It appears to be a classic rise and fall story,” says New York Social Diary editor David Patrick Columbia. “In New York society, money is the ticket. If she has the money, she will be taken seriously.” If Blouin’s fortune disappears, however, it’s possible her high-minded cohorts will abandon her as well.

What is it that drives Blouin, who didn’t respond to interview requests, to keep up appearances in the face of discord and negative press? Vanity, perhaps? Or denial? Pride?

If we’re to believe Blouin, the talk of turmoil is just noise. “The company is not having money problems,” she told the Observer in early 2014. “And we have our business that is really growing… Are we making mistakes? With the growth that we’re doing, we probably are.”

Just before the Creative Leadership Summit, one of Blouin’s business-side soldiers responded—via “reply all” (presumably by accident)—to a colleague’s company-wide farewell note: “So sorry to hear you are leaving, but not surprised… so many good people have left due to mis-management.”

Blouin’s rebuttal was a 1,021-word e-mail meant to counter the critical employee’s “disgraceful” note. But it could have also betrayed an unwillingness to bow to defeat. “Maybe we had to go through this up and down to know whom we wanted to work with in the future,” Blouin wrote. “I am proud of all the team to have built the awareness that is meaningful for this world’s cultural dialogue. I am proud of those who have contributed to this respectable venture and that will embrace it moving forward because we feel that getting up and [being] in an industry that helps the world is what matters.”

After all, Blouin is still publishing well-regarded titles covering the art world. And, for all her apparent troubles, she’s displayed a willingness to invest in journalism and philanthropy and a committed refusal to fail. As she herself noted in the aforementioned staff e-mail: “Do not judge those that try.”