It's Anna Wintour's 20th anniversary as editor of Vogue, and the be-bobbed one has certainly earned her title as one of the most feared figures in fashion. But it's worth remembering that she hasn't had a smooth ride. In fact, Wintour was beset by a salacious—and probably false—sex scandal rumor as soon as she took her job. Here, from the pages of Jerry Oppenheimer's biography Front Row, is the story of the alleged Wintour love connection with her boss, Si Newhouse—and how Wintour's reaction became a rare and fleeting moment of feminist pride inside Conde Nast:

An associate of Jann Wenner says the Us Weekly owner-rumored to be ready to sell the title to a magazine group such as Condé Nast-isn't so attached to the celebrity weekly. It's vastly profitable but doesn't really understand the modern pop culture from which Us Weekly plucks its stars. The source tells today's WWD: "It's not really his world, not like Rolling Stone, a world he instinctually understands." But just how clueless is the 62-year-old former hippie, who founded Rolling Stone at the age of 21 after dropping out of Berkeley? His minions joke that Wenner's musical evolution ground to a halt some two decades ago. He's never quite figured out that Us Weekly staple Beyoncé has one of those accents at the end of her name. Wenner refers to her as be-yons, much to colleagues' amusement. One hopes he doesn't refer to his hoped-for buyer as "cond-nast".

Last week Charlie Rose wondered if Conde Nast was trying to buy Rolling Stone. Now Keith Kelly reports that they're actually trying to buy Us Weekly, Jann Wenner's other, more valuable but less cherished property. The "price tag could hit $750 million," according to the Post. Which would give Wenner enough cash to continue running Rolling Stone into the ground for decades to come. Us does seem like a more likely target for Conde Nast, but the high price and the overall print market these days are cause for skepticism. And though Charlie Rose may have gotten it wrong on that particular issue, that interview's main benefit stands: it is still accurate to call Graydon Carter a "self-described pussy." [NYP, Previously]

"Jann Wenner is said to be quietly exploring a sale of celebrity magazine Us Weekly to Condé Nast and the price tag could hit $750 million." [NYP]

FOLIO magazine spotted a juicy bit at the very end of a Charlie Rose interview earlier this week with Vanity Fair chief Graydon Carter and Rolling Stone editor Jann Wenner. Rose casually asks, "What's this story that Conde Nast wants to buy Rolling Stone?" That triggers a look of sheer terror on Graydon Carter's face, and a great deal of forced laughter and jabbering between the guests. We think we can hear Graydon saying, "We'll see." What it does not trigger is a denial. RS would certainly be a decent pickup for Conde Nast, but what the hell would Jann Wenner do with himself if he sold out? (Then again, Jeff Bercovici thinks Wenner's company is in a permanent decline, and he should cash out). Click to watch the clip, and parse the reactions carefully. [If you have any further info, email us.]

Sarah Chubb is not just the president of CondeNet, the online division of Conde Nast—she's also a "nationally ranked cyclist." And she's damn tired of you plodding runners hating on her cycling style in the wild streets of Central Park, for real! "There is a lot of hate," she tells New York mag. "The Road Runners club can take over the entire park, and they get pissed at us if our races go past 8 a.m. The runners don't stay where they're supposed to stay, they're wearing headphones, and they'll scream at you if you ask them to get out of the way!" Fools. If you think that CondeNet president Sarah Chubb will hesitate to run you over at high speed, well, you don't know anything about making it in the media. [NY Mag. Pic via NYO]

Mark Jarecke, creative director for Condé Nast web properties such as Style.com, has left Newhouse family's magazine group. Jarecke was a key aide to the web sites' editorial director, Jamie Pallot. Anyone have the backstory?

Radar runs a tangled tale of the junket to Las Vegas financed by email newsletter Thrillist and the righteous indignation it provoked from media ethics cop Jeff Bercovici. The Portfolio media reporter tried to catch out two reporters for the New York Post invited on the trip; but forgot to mention that one of his own Condé Nast colleagues was also along for the ride.

At a party Wired threw for its Reddit social news site tonight, to celebrate the release of its software as open source, I pressed Wired News editor Evan Hansen for details on HotWired, the tired Web brand his corporate overseers at Conde Nast are planning to revive. He didn't tell me anything — except that the social network Wired editor Chris Anderson has been talking about is not, in fact, HotWired. Correction appreciated, Evan. HotWired, whatever it is, is far enough along to be part of Wired's PR boilerplate. A press release for Wired property Reddit included this phrase: "HotWired's development is TBD." To be determined. That's the point at which I became bored.

Magazine groups are changing their management with all the abandon of the fractious Meade family in Ugly Betty. The latest casualty: dorky Victor Ganzi, who's stepping down as chief exec of Hearst with no successor lined up. (That's always a bad sign.) Magazine bosses must be feeling particularly insecure today. The rumors about Cosmopolitan publisher Hearst in the Wall Street Journal come the day rival magazine group Hachette dropped its boss of nine years. That leaves S.I. Newhouse's Condé Nast an island of stability-as long as the forgiving 80-year-old publishing magnate remains in charge. (Have the backstory on the sudden Hearst reshuffle? Email!) Update: At least Hearst isn't pretending this was in any way planned. "The reason for his resignation was irreconcilable policy differences with the Board of Trustees about the future direction of the company." And Meredith-which publishes a range of tepid lifestyle magazines such as More-just dropped its editorial director.

Chris Anderson, Wired's waggle-eared rock-star editor, has been dropping hints left and right about the relaunch of HotWired, a faded Web property Conde Nast picked up along with Webmonkey last month. The rumor we've heard: That Wired is relaunching the site as a news-focused social network like Digg. (Conde Nast already owns Digg competitor Reddit, whose engineers are likely involved in the project.) It's a sensible brand extension for Wired, but a far cry from HotWired's early ambitions, described in a 1994 email as "live, twitching, the real-time nervous system of the planet." Here's the HotWired FAQ, which reads like it was just unearthed from a time capsule:

Vogue editor Anna Wintour should turn down the British medal she's being offered for several reasons. First of all because the title-Officer of the British Empire-is ridiculously outmoded. It marks the 58-year-old fashion veteran as a member of an earlier generation of Brits who still hanker pathetically for approval of the fusty home-country establishment decades after moving to the US. But most of all Wintour should be embarrassed to take an honor a rank below that of her long-time rival, editor Tina Brown. The one-time Vanity Fair editor is a Commander of the British Empire, which means she'll outrank Wintour in the ridiculous "order of preference" of English society.

A media company identifying itself as "Cond Nast Publications" is in need of a copy editor. Specifically, the ad says, "TheAssociate Copy Editorreviews copyedited text." Urgent, please apply now! Click through for a screengrab of thisjobopportunity.

Kevin Kelly, Wired's past in-house futurist, has given an interview in which he makes the seemingly ludicrous claim that Wired could have been Google. The New York Observer has a giggle at Kelly's statement that "from the very beginning, Wired believed in 'search.'... I believe that had Wired not been divided and sold that we might have actually arrived at the same place that Google had." But was Kelly really that far off? Watch the whole video and see

MIDTOWN WEST — "You're a normal person," Wired editor Chris Anderson asked me at Wired's 15th anniversary party last night in New York. "What do you make of all this?" He nodded his head toward the four corners of the roof top, crowded with the Wired set. In response, I said something about the thick-rimmed black frames and all the scarves. But for reading-comprehension points, I should have said I felt like I was in the midst of a cult. Because that's what Conde Nast's Wired is all about, Anderson and Wired cofounder Louis Rossetto told us in their speeches: turning the cult of technology into a culture, but keeping it as fervent as a cult. That and covers of a nude Jenna Fischer and LonelyGirl15 in bed, of course. Below, photos of the faithful.

TechCrunch reports that CondeNet, the online arm of Condé Nast and the parent of Wired.com, has bought Ars Technica, a rival technology news site. But if the latest issue of Wired is any indication, that's not the only tech property that's moved to CondeNet recently. On page 24, Wired's June issue announces a new version of Webmonkey, a defunct site for Web developers, under a list of Wired.com features:

A Grand Theft Auto obsessive has matched up vistas from the hit Rockstar videogame with the real New York City. Here's the Conde Nast skyscraper in Times Square (at left) compared with the equivalent tower in Liberty City's 'Star Junction' (at right). Any GTA fans want to create mayhem in the magazine group's lobby, mow down a few Vogue interns, and send us a videograb of the results? [Matthew Johnston's Flickr page]

Is Conde Nast building a breast-pump station at 4 Times Square? According to someone, "Just heard that [they're] building an office for their lactating mommies to breast pump and gossip." Is this true? Email sheila@gawker.com. We need more info!

Portfolio editor Joanne Lipman is to ring the stock market's opening bell tomorrow morning at 9.30am, to mark the first anniversary of the Conde Nast business magazine. It's a distinct honor for Portfolio, or would be-but for one detail. Lipman will be kicking off trading not on the real floor but on the Nasdaq electronic exchange. The ceremony will take place at the Nasdaq's unpopulated "market site" round the corner from the magazine's offices-before an audience of bewildered Times Square tourists. (Easy dig: they may represent the confused business title's target demographic.)

Social news aggregator — that is to say, Digg clone — Reddit is working on a redesign. Online media consultant Brent Csutoras landed leaked screenshots. We've annotated them for your convenience.