The late Steve Florio–the larger-than-life, charmingly hyperbolic chairperson and chief executive of Conde Nast who died in 2007 — liked to tell colleagues about going to lunch one day with Vanity Fair editor Graydon Carter very early in what turned out to be Carter's celebrated 25 -year tenure.

It was an anecdote that, more than two decades later, might offer a glimmer of hope and optimism to Vanity Fair ‘ s next editor, Time publication and New York Times alum Radhika Jones, as she prepares succeed the legendary Carter on Dec. 11.

In Florio's account, as soon as the two men took their seats in the dining room of the Royalton Hotel, a favorite Conde Nast watering hole, the Canadian-born Carter blurted out:” Is this the lunch where you fire me ?”

Carter may or may not have said that out loud, according to an informed source. But if he didn't say it, he was certainly thinking it.

His upward trajectory since that moment could serve as an encouraging object lesson.

Yet this week Jones discovers herself stepping into what might be called an exceedingly fraught situation, redolent of the anxiety and paranoia that nearly always accompany major changes at Conde Nast.

” I have a lot of friends who work at Vanity Fair . They're all freaking out ,” said a well-connected editor who, like several others quoted in this story, requested anonymity in order to speak frankly.” I guess all the staff are in anxiety. They know that they've been on the gravy train for a long time. Clearly she's going to have to go through the contributors and weed them out .”

A second editor, however, cautioned that a wholesale bloodletting of legacy the authors and editors would be profoundly unwise.

” Learn how the previous generation did it before you attain your changes–in other words, learn how to write a sonnet before you write free verse ,” this person said.” It's a big ship and those older people know where all the duct videotape is. They have the institutional memory, whereas the 23 -year-olds are not going to be ready for that just yet .”

The vaunted Conde Nast gravy train has plainly run out of steam. Nine years after the publication business imploded with the deep recession of 2008 and 2009, Conde Nast is grappling with the same unpleasant realities tackling every other publisher.

Even Carter–who scored a temporary victory last year against a corporate cost-saving strategy that would have necessitated Vanity Fair to lose its dedicated creative director and fact-checking department in a consolidation move with other Conde Nast titles–has been putting out the magazine on around 60 percent of its pre-recession budget, says a knowledgeable source. Once-lavish contracts that rewarded contributing editors with monthly stipends have all but faded, and most contributors are instead paid in respect of a piecework basis.

The current issue is graced by a meta satirical exchange of letters between Carter and a fictional contributing editor, Edwin Coaster, who is offering to write a chronicle of his serious illness and demise.

” The days of a writer's getting a six-figure bargain to do a column-by-column diary of his pending demise are long gone ,” the fictional Carter writes back in his rejection letter.” In the old days, I paid Molly Ivins $ 20,000 for fifteen hundred words on her struggle to open a mayonnaise jar, and we sent a livery driver in a Rolls-Royce Silver Cloud III all the way to Texas merely to pick up the jar and bring it back to New York so our fact-checker could confirm that it was unopenable .”

According to the New York Times , 2017 is expected to generate $100 million reductions in revenue for Conde Nast than last year's proceeds; 80 employees across the company's 20 publication titles are slated to lose their jobs; GQ , Glamour and Architectural Digest are being forced to reduce the frequency of their print editions; and Teen Vogue is discontinuing publish publication solely to become a web-only enterprise.

Jones, meanwhile, is being hired at a significantly lower salary than her predecessor; her rumored starting salary of $500,000 – $600,000 a yearpales by comparison to Carter's reported$ two million deal.

” It's a bit of a glass cliff ,” said a prominent editor.” Women always get carried in to do the jobs that feel undoable .”

The Harvard-educated Jones is, by all accounts, a brainy academic who cut her journalism teeth at such rarefied and erudite publications as Paris Review , Artforum and Moscow Times , and received her comparative literature doctorate from Columbia University; at Time magazine, she started out nine years ago as an arts editor.

Her most recent job–editorial director of the New York Times' book coverage–is barely a traditional calling card for resulting a glossy monthly devoted to pop culture, celebrity, and sumptuous photo spreads of Hollywood stars–a fizzy concoction leavened by deeply-reported articles on politics, foreign affairs, culture and history.

The current issue features “J-ROD!” on the encompas (” JENNIFER LOPEZ and ALEX RODRIGUEZ on Love, Beauty and Redemption ,” a puffed piece written by contributing editor Bethany McLean ). Also teased on the covering are a Joe Biden interview and an excerpt from his new book( with portraiture by Annie Leibovitz ), an investigative piece by Michael Lewis on” Trump's Cruel War on Rural America ,” a retrospective on the life of Margaret Trudeau, the former Canadian first lady and mom of the present prime minister, and a narrative titled” Meet London's Kardashians .”( Do we have to ?)

Jones's most relevant credential to run Vanity Fair , arguably, was overseeing the annual Time 100 Gala for several years before she joined the newspaper of record a year ago; yet her decidedly un-glitzy profile to date could well be an advantage in terms of managing the expectations of the world at large.

She comes to her new undertaking with no existing mandate to trim expenses, and, officially anyway, has free rein to build Vanity Fair her own. But according to half a dozen publication denizens who spoke to The Daily Beast on condition of not being named, Jones's new duties will inevitably require her to slash the masthead, cut freelance fees and editorial budgets, oversee shrinking print advertising revenue, and boost the magazine's live event business and digital presence.

She'll be doing all that and more while playing the unenviable and no doubt unwilling role of grist to the media rumor mill.

The March 2018 issue will be the first to bear her imprint.

” The learning curve will be very immerse for her, because she hasn't done the job before–and actually it's a very difficult job ,” said a Conde Nast Kremlinologist.” Arguably it's harder to enter a publication and make it relevant now because you're up against much more competition online .”

Jones will be at pains to figure out a route to build Vanity Fair more pertinent and news-breaking than it has been in recent years, but with fewer financial resources, said several editors who described the publication as surprisingly slow off the mark on the Donald Trump phenomenon and the Harvey Weinstein sexual misconduct scandal–and sexual misconduct in the film industry generally–especially because Hollywood has historically been Vanity Fair ‘ s wheelhouse.( In next year's Hollywood issue timed to the Oscars, Carter will make a cameo appearance–Alfred Hitchcock-like–amid the three-panel covering display featuring the most wonderful performers and actresses .)

And while several editors praised the immediacy of” The Hive ,” the magazine's web-only editorial product which launched in June 2016, they noted that like much of Conde Nast, the publication has been late to the game in its digital presentation and exploitation of video.

Still, Vanity Fair &# x27; s digital director Michael Hogan noted that, according to the web analytics service Omniture, the number of unique tourists to 17 million per month from August through October of this year-has increased by 428 percent since October 2013.

” You've got to inject some new life into it ,” said the Kremlinologist.” They've got to bring in new people, clear out old people, and she's going to have to learn how to be an editor in chief .”

And if the gossip-driven Conde Nast corporate culture remains true to form, Jones is” going to be up against a lot of hostile editors and novelists who are going to talk to you, [ New York Post media columnist] Keith Kelly, and whoever else is out there online–which will be designed to undermine her .”

” If you fail everybody will know it ,” a different editor told The Daily Beast.” It's not like you're failing at some obscure web site in Seattle. This is like the Yankees .”

In press interviews with her former employer, the Times , and her future one, Vanity Fair , Jones has been cautious and elusive about her plans and point of view, much like a Supreme Court nominee testifying before the Senate Judiciary Committee.

” I need to get oriented first–there's a lot to take in ,” she told the Times .” I'm just really interested in discovery .” She added vaguely,” It's hard for me to exactly figure out when I became obsessed with publications .”

In an oddly impolitic( but refreshingly honest) admission, Jones to be recognised that when she was growing up( still in her teens when Carter took the helm) she only read Vanity Fair “on and off.”

Jones was chosen over a slew of better known and more experienced candidates who reportedly included the Hollywood Reporter ‘ s Janice Min, New York ‘ s Adam Moss, GQ ‘ s Jim Nelson, Smithsonian ‘ s Michael Caruso, People ‘ s Jess Cagle, and even Times “Dealbook” columnist and CNBC personality Andrew Ross Sorkin.( It's uncovering that Carter, a college dropout, had never heard of Jones until a couple of weeks ago as she emerged as a finalist for his job, according to sources; and until she was announced as his successor Monday at Conde Nast headquarters in One World Trade Center, Carter had never met her .)

Jones was the favorite candidate of New Yorker editor David Remnick, who–along with Conde Nast artistic director( and Vogue editor and publisher) Anna Wintour–was tasked by Conde Nast chief executive Bob Sauerberg to interview likely prospects, solicit their action-plan memorandas, and present Sauerberg with a culled list of the most promising candidates.

Wintour's preference, according to sources, had been Janice Min, a celebrity editor in the tradition of Brown, Carter( and, for that matter, Wintour ), who constructed a reputation for aggressive celebrity journalism when she operated Jann Wenner's Us Weekly more than a decade ago and years later when she remade the Hollywood Reporter from a sleepy trade publication into a news-making web site and a must-read glossy weekly.

Wintour's fave, Min–who has been earning seven-figure wages since her Us Weekly days–would have come at significantly higher price than Jones. But she is a known sum in Hollywood, has longstanding relationships with high-end advertisers, and arguably would have hit the ground running and would been better positioned to create buzz and attract ad revenue.

Ironically, according to sources, it was Carter who raised objections months ago when Wintour and Sauerberg were considering acquiring the Hollywood Reporter for Conde Nast; he warned them that the revamped trade sheet–whose movie star and media coverage is similar to VF ‘ s–was likely to be a money-loser for the company, and that such a plan would be” a terrible notion .” In the end, it didn't happen.

In the early 1990 s, on the day that Florio and Carter lunched together, Conde Nast was flush with cash, and Vanity Fair ‘ s budget shortfalls were liberally subsidized by the massive earnings of Glamour , the privately-held company's golden egg-laying goose.

The late Conde Nast chairwoman S.I. Newhouse ran the family-owned business with an eye toward opulence, was famously supportive of his editors, profoundly loved his magazines, and spared no expenditure to achieve his vision; he had personally recruited Carter and was invested in his success.

Yet even Carter–who came to the iconic, Hollywood-centric glossy after toiling at Time , founding Spy publication and running the New York Observer — initially had a tough run of it trying to establish VF's refreshed mission and new identity with luxury advertisers and kibitzers in the media, while corralling a staff of sometimes difficult the authors and recalcitrant editors to instill a sense of importance and innovation.

The optics were especially difficult, of course, after the illustrious eight-year operate of Tina Brown( afterwards the founding editor of The Daily Beast ), who took over VF when it was a highbrow, pompously literary culture mag–led, ironically, by a former New York Times editor who'd had similar bookish responsibilities to Jones's–and turned it into an urgent must-read; Brown had gone on to remake the New Yorker, VF's corporate sibling, from the sometimes staid and precious periodical of the William Shawn era into an occasionally indecorous, media-savvy weekly buzzing along with the news cycle.

Brown–who has just published a book-length account of her VF years, The Vanity Fair Diaries –had this advice for Radhika Jones as she presumes her new responsibilities.

” Oh, completely rip it up, and start again if you want ,” Brown told Time magazine.” I'm a huge believer in reinvention. And we put out astounding DNA that lasted for, good lord from' 84 to where we are now. It's time for it to be rethought. I don't think you want to stay in template left by your predecessor .”

In an email to The Daily Beast, Brown added that Jones's VF should” find new voices of women who are changing the culture” and” needs to be much more global” with” more emotional content and big narrations out of VF &# x27; s traditional convenience zone .”

It's unlikely anymore, however, that any such convenience zone exists.

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