Ever since Donald Graham, the heir to the Washington Post, decided to sell the family’s newspaper for two hundred and fifty million dollars, in 2013, to Jeff Bezos, the founder of Amazon and one of the world’s richest men, the preferred solution for a financially struggling publication has been to find a deep-pocketed billionaire, with other sources of income, to buy it and run it more or less as a philanthropic endeavor.

That seemed to be what the Wenners—Jann, the father, and Gus, the son—had in mind, too, when they put Rolling Stone, the iconic magazine founded by the elder Wenner, fifty years ago, up for sale recently. He told the Times that he hoped to find a buyer who understood the magazine’s mission and who had “lots of money.”

But the story of Alice Rogoff and the Alaska Dispatch News is a cautionary tale that shows the limits of what a wealthy owner is willing, or able, to do for a struggling newspaper in the digital era. Rogoff is the wife of David Rubenstein, the billionaire co-founder of the Carlyle Group, the publicly traded, Washington-based private-equity behemoth. Rubenstein, with a net worth estimated by Forbes at nearly three billion dollars, is no stranger to lost causes. He provided $7.5 million to rebuild parts of the Washington Monument, after the 2012 earthquake, as part of his ongoing and iconoclastic “patriotic philanthropy” effort. He provided $18.5 million to restore the Lincoln Memorial. He provided twenty million dollars in cash to restore two buildings on the property at Monticello, the home of Thomas Jefferson, as well as to restore two floors of Jefferson’s home itself. He owns original copies of the Magna Carta, the Declaration of Independence, and the Constitution. He has a copy of the Emancipation Proclamation and the Thirteenth Amendment, which abolished slavery. He is the chairman of the board of Duke University (my alma mater, too) and the chairman of the board of the Kennedy Center. He is a co-chair of the board of trustees of the Brookings Institution and the chairman of the Council on Foreign Relations. He has an interview show on Bloomberg TV. He has agreed to take the Giving Pledge and donate half his wealth to charity.

By all accounts, though, the Alaska Dispatch News was Rogoff’s baby. She reportedly fell in love with Alaska after a trip there in 2001, according to the Los Angeles Times. She explored the Arctic, hunted moose, and flew her own plane. A graduate of Connecticut College and Harvard Business School, Rogoff spent ten years as the chief financial officer of U.S. News & World Report and was also an assistant to Graham, when he was the publisher of the Washington Post. She bought the Alaska Dispatch News in March, 2014, from the McClatchy Company, for thirty-four million dollars, when it was known as the Anchorage Daily News. She promptly changed its name and bought a new printing press to leave little doubt that she was committed to continue to print the paper. “I don’t see an end to print,” she told the Los Angeles Times last year, explaining why she bought the paper and the new press. “If I could see it, I’d be preparing for it. We’re not.” She said that she hoped to continue publishing the paper, which had a paid circulation of about forty-two thousand, for “decades to come.” After buying the paper, she sold certain assets for some fifteen million dollars and used the proceeds of that sale to reduce the purchase price. She put in six million dollars of her own money and borrowed another thirteen million dollars from Northrim Bank.

But Rogoff’s dream of running a local newspaper in her beloved Alaska—she often lived there apart from her husband—slammed into the economic realities of the newspaper business. In August, the Alaska Dispatch News filed for bankruptcy protection. Rogoff had been trying to sell it for months, without success. According to the bankruptcy filing, the paper was losing an average of a hundred and twenty-five thousand dollars per week and owed its venders some $2.5 million. She still owes Northrim Bank around $10.2 million, the security for which is the regular payments that she receives as part of a “marital settlement agreement” with her husband, as well as her Wells Fargo investment accounts and the remaining assets of the paper. (The couple are not divorced, though they have mostly lived apart—on opposite coasts—for many years.)

In announcing the bankruptcy filing to readers, on August 12th, Rogoff struck a poignant and bittersweet note. “I think by now that most of you know owning this news organization has been a labor of love for me,” she wrote. “The body of work done in our time has been as good as we could hope for. We’ve worked hard to help illuminate the issues of our day and provide a platform for points of view from across Alaska. Yet like newspapers everywhere, the struggle to make ends meet financially eventually caught up with us. I simply ran out of my ability to subsidize this great news product. Financial realities can’t be wished away.”

Last month, a bankruptcy judge in Alaska approved the sale of the newspaper to a new group of buyers, led by the Binkley family of Fairbanks, for a million dollars—the amount of the loan that the family had made to the paper a month earlier to keep it going. Very little, if anything, of that million dollars will go the paper’s existing creditors. “Obviously, this is not the outcome I would prefer,” Rogoff wrote in a court filing, “but the reason I agreed to these terms is that my primary desire is to see that the newspaper continue in operation.” For their part, the Binkleys made their fortune over five generations by taking tourists and freight up the Yukon River. They are determined to keep the paper going. “Newspapers across the country are in distress and operating independently in remote Alaska adds to the challenge,” Ryan Binkley wrote to the paper’s readers. “We will be working with the talented and dedicated team here at the company, building a winning organization. The ADN can’t be allowed to go away. It’s too important to the city of Anchorage and to the State of Alaska.”

In the three years that Rogoff owned the paper, its value declined ninety-seven per cent. Sure, she had deep pockets, but not deep enough, it turned out. (Certainly, had she had full access to her husband’s multibillion-dollar fortune, or had he been interested in this particular lost cause, she likely could have kept running the paper, which lost $6.6 million in 2016, a million dollars more than it lost the year before, according to the financial statements filed in bankruptcy court.) She will likely end up losing the six million dollars that she invested, plus whatever portion of the $10.2 million that she still owes the bank, as part of the more than seventeen million dollars she told the bankruptcy court that she invested in the newspaper and the new printing press, which, according to the bankruptcy filing, remains unused and sitting idly in an old building in Anchorage. As for Rogoff herself, the Los Angeles Times reported that she left the bankruptcy hearing last month virtually unnoticed “and disappeared down the street without further comment.” Her Alaska attorney, Cabot Christianson, told the paper that she would continue to live in Alaska. (He declined my request to be interviewed about how it went wrong for Rogoff. She stopped tweeting last November.) “It is extremely painful,” she told the bankruptcy judge about the paper’s dénouement.

Of course, Rogoff’s debacle is emblematic of a much bigger financial crisis in American journalism. Even with the arrival of a handful of rich backers—Bezos, at the Post; the Sandler family, at ProPublica; and Laurene Powell Jobs, at The Atlantic—the broader industry has failed to find a viable digital-news model as traditional forms of revenue—advertising and subscriptions—continue to evaporate like rain in the Sahara. (Even Condé Nast, the owner of The New Yorker, is not immune to the macroeconomic forces affecting the industry.) In an era when the Presidency demands more and better reporting than ever (and there has been much fabulous reporting), newsroom staffs continue to shrink. According to the annual survey conducted by the American Society of News Editors, thirty-two thousand nine hundred full-time journalists were employed in newsrooms across the country in 2015, down from fifty-seven thousand in 2007. (The organization has since modified the survey.)

It’s difficult to see where all this is going. ProPublica just announced a program to pay for investigative reporters in local newsrooms across the country. That’s a positive step for journalism and our democracy. But the Alice Rogoff saga is a reminder that sometimes deep pockets are not enough to save a local newspaper. Creating indispensible journalism—whether at the local or national level—is not without cost. It does not want to be free. If people aren’t willing to pay for it, like they pay for the Internet or cell-phone service, then it will surely disappear, sometimes right before your eyes.