If Hell froze over, pigs took wing, sheep fell from the sky, and snow blanketed Hawaii, it still wouldn’t be as astonishing as Monday’s announcement that the storied Graham family is selling The Washington Post to a billionaire online-retailing entrepreneur.

Amazon.com founder and chief executive Jeffrey Bezos, whose net worth has been estimated at $28 billion, has agreed to pay $250 million in cash to take possession of the 136-year-old newspaper and several related media properties within 60 days. Bezos’s acquisition is personal, not corporate, so The Post will once again be a private entity—something it hasn’t been since the Grahams took the company public in 1971. In one of the more jarring aspects of the deal, the newspaper’s longtime parent company will be required to change its name (though it will keep its downtown Washington headquarters and several other real-estate holdings).

“It’s very sad,” said Post associate editor Bob Woodward, who, along with his partner Carl Bernstein under the leadership of executive editor Ben Bradlee, led the Post to a Pulitzer Prize for their investigation of Richard Nixon’s crime-ridden White House. “But if there’s somebody who can succeed, it’s Bezos. He’s the innovator, he’s got the money and the patience, so we’ll see. I think in some ways, this may be the Post’s last chance to survive, at least in some form of what it was.”

Woodward’s bittersweet reaction was typical of Post veterans, who were at once grief-stricken at the prospect of losing the Grahams as owners and hopeful that Bezos will find a way to save their jobs.

‘There is unquestionably some element here of a highly successful guy buying a seat at the table. Citizen Kane 2.0,’ said Jim Friedlich.

“I spent my entire adult career working for the Graham family, and even though The Washington Post is corporate, it never felt much like one. I loved that sensibility,” said associate editor David Maraniss, a Pulitzer Prize–winning biographer of Bill Clinton, Vince Lombardi, and Barack Obama. “That will be gone now. Some of my friends are saying that in the long run, this is a great thing, because they’ll be much smarter about using the new media and help the paper. That might or might not be true. But my feeling right now is one of loss.”

Longtime feature writer and religion columnist Sally Quinn, wife of Ben Bradlee, was one of the few who said she isn’t surprised by the decision to unload The Post, which accounts for a small portion of revenue for a public company that is largely focused on educational products and services. “I know the board has been agitating,” she said. “I think Jeff Bezos is probably the best possible choice they could have made.” As for whether she’s feeling sad, “I’m an army brat. I didn’t live anywhere for more than a year and a half in my life,” Quinn said. “Change happens. Life moves on.”

Former executive editor Leonard Downie told The Daily Beast, “I’m obviously in shock and stunned,” adding jokingly that “it’s helping a lot being interviewed by people. At least I’m doing something. It’s therapy, I guess.” But Downie insisted, “I’m cautiously optimistic about this. I think this is a big sacrifice on Don’s part, because he loves the paper so much. But I think he believes he’s doing the best thing for it and for its future … I have no reason to doubt that.”

So ends 80 years of Graham-family control through the Great Depression, World War II, the McCarthy Era, the Pentagon Papers, and the Watergate scandal, the event that transformed journalism, toppled a presidency, and established The Washington Post as a national institution.

Monday afternoon’s revelation, which came hours after the Post Co. board ratified the sale, totally blindsided the financially battered news industry that is feverishly trying to crack the code on how to squeeze money from the Internet and other technological innovations, while still digesting The New York Times Co.’s $70 million sale of The Boston Globe and The Worcester Telegraph & Gazette last week to Red Sox owner John Henry for a tiny fraction of what the Times Co. paid for them decades ago.

Times Co. chairman and publisher Arthur Ochs Sulzberger Jr., who recently told The Daily Beast that a robust and competitive Washington Post is essential to the long-term health of his own family-controlled newspaper, was said to be “stunned” by the sale, which the Post Co. secretly initiated with the Allen & Co. investment bank to find qualified bidders.    

The negotiations for the Post were closely held, and the deal “seriously progressed,” according to a knowledgeable source, when Washington Post Co. chairman and CEO Donald Graham sat down with Bezos during last month’s Allen & Co. annual media-and-technology conference in Sun Valley, Idaho.

“Every member of my family started out with the same emotion—shock—in even thinking about” selling the paper, Graham told the Post’s Paul Farhi in an interview. “But when the idea of a transaction with Jeff Bezos came up, it altered my feelings.” Graham, who has been friendly with Bezos for the past decade, added: “The Post could have survived under the company’s ownership and been profitable for the foreseeable future. But we wanted to do more than survive. I’m not saying this guarantees success, but it gives us a much greater chance of success.”

Prominent digital-media adviser Jim Friedlich agreed with that assessment. “Bezos brings a combination of digital-commerce savvy and deep pockets,” said Friedlich, who is president of Empirical Media (which has advised The Daily Beast). “His history at Amazon was to sustain extended losses to buy commanding market share. He is demonstrably someone willing to invest for the long term. This is precisely what great newspapers in transition require in order to come out the other side as thriving digital brands.”

Friedlich added that Bezos, who recently invested $5 million in the Business Insider Web site, is well positioned at the Post to take advantage of the promising trend of readers being willing to pay for quality digital content at outlets such as the Times and The Wall Street Journal. Bezos also might be thinking of adding other properties to his portfolio “in both digital and legacy media. He has both the money and the vision to think big.”

A possible downside, Friedlich said, is that “there is unquestionably some element here of a highly successful guy buying a seat at the table. Chris Hughes at The New Republic, John Henry in Boston, Jeff Bezos in Washington. Citizen Kane 2.0.”

Mort Zuckerman, a billionaire real-estate developer who for the past two decades has had a seat at the table as owner of The New York Daily News, also was hopeful that Bezos will work to keep The Washington Post ahead of the digital curve. “I can’t imagine that he got involved without having a lot of positive ambitions for the paper,” Zuckerman said (although Bezos, notably, has not really said what drove him to enter the newspaper business). “He’s really a very talented man.”

Executive editor Marty Baron, who joined the Post seven months ago from the Globe, has known about the impending sale since last week and proved that he can keep a secret. He’s also bullish on Bezos, who, after all, will soon be his boss. “If we’re getting a new owner, we couldn’t ask for a better one,” he said, adding that he's hoping soon to actually meet Bezos, who was not on hand for Monday’s announcement. “He certainly understands how technology is changing, how consumer preferences are changing. He is a damn savvy business person, and he can contribute a lot to the Post as it navigates a very different media landscape.”

The 68-year-old Graham—son of legendary publisher Katharine Graham and grandson of Wall Street financier Eugene Meyer, who bought the paper in 1933 for $825,000 at a bankruptcy auction—choked up as he announced the sale to dumbfounded employees in the converted pressroom that serves as the company auditorium.

Graham’s momentary loss of composure came as he was finishing up reading from a prepared statement about the transaction, unusual for a man accustomed to speaking off the cuff. Graham was a D.C. cop and combat soldier in Vietnam before he worked his way up in the newsroom, and is adored by many of his employees; his sentiment was reciprocated by the tearful overflow crowd gathered at the Post Co.’s downtown Washington headquarters.

“The whole place was very emotional,” a witness told The Daily Beast, noting that Graham’s brief talk was followed by his niece, Washington Post publisher Katharine Weymouth, sharing an encouraging letter from the 49-year-old Bezos to his future employees, in which the mogul pledged to maintain the paper’s “values,” stick to his day job in Seattle, and leave the day-to-day running of the Post to the “excellent leadership team that knows more about the news business than I do”—including Weymouth, Baron, and editorial-page editor Fred Hiatt.

“The other extraordinary thing that happened,” the witness recounted, “is that after Katharine and Don answered some questions, Don said, ‘It’s time to get back to work. We gotta put out a paper.’ There was a pause, and then long, sustained applause, which was, for Don, a very emotional moment.”

Chip Brown, a former Post reporter who interviewed Graham in 1999 for a study of how various legacy newspapers were preparing for the digital age, recalled that the Post Co. chairman was both knowledgeable and excited concerning the advent of online journalism.

“He was really on top of this thing early,” Brown said, “and he still didn’t understand what hit him, I guess. It’s like a batter not being able to get away from this fastball coming right at his head … Nobody cared about the paper more than Don Graham. It must kill him to have to let it go.”

Brown added: “The Grahams were incredibly proud of their family ownership. They fought to maintain family ownership. At the height Watergate, when it went public, and they were possibly losing control, the Nixon administration came after them. They survived the Nixon administration, but they didn’t survive the Internet.”