When the great granddaddy of opinion journals, The New Republic, abruptly vanished in a sad, squalid burst of pixel dust and management theory last winter, establishment journalists rent their garments and gnashed their teeth in horror. “The promise of American life has been dealt a lamentable blow,” a group of former writers and editors associated with the magazine pronounced in a public statement. The New Republic, they said, formerly “a kind of public trust,” had now suffered “its destruction in all but name.”

In-house disputes over how the august policy organ should adapt to the digital age had claimed the jobs of editor Franklin Foer and literary editor Leon Wieseltier. A mass walkout ensued, with more than thirty writers, editors, and contributing editors forsaking the shop even before Foer’s designated successor, onetime Gawker editor Gabriel Snyder, could fire up his company email account. Chris Hughes, the thirty-one-year-old former Facebook mogul who acquired The New Republic in 2012 amid a round of adulatory press reports hailing the marriage of Silicon Valley largesse and Beltway savvy, now stood contemplating his handiwork in an all but vacant New Republic office, not long after he’d presided over the magazine’s one-hundred-year gala. Happy Anniversary.

The extraordinary—and largely portentous—burst of commentary that followed suggested something more was at stake than the bust-up of a magazine long past its prime. A month earlier, similar convulsions had upended the management team at another journalistic concern, one whose digital identity had been settled from the first: First Look Media, the pet project of eBay billionaire Pierre Omidyar. There, Rolling Stone muckraker Matt Taibbi and John Cook—another former Gawker editor—had bailed out of their plum positions editing Racket and The Intercept, two much-ballyhooed First Look startups with a roster of top-drawer writing and editing talent. (Racket, indeed, was permanently mothballed after Taibbi fled.)

For a few months there at the end of 2014, it was as if the crown princes of digital innovation had become Midases in reverse, repelling experienced journalists in droves, even in the face of one of the most depressed markets for journalism work in modern history.

Those thousand think pieces bloomed, all seeking to shed new light on the strange mores of tech-industry moguldom, and on how the inventors of the future had failed to match up to the tough-minded folkways of magazine-style journalism and the notoriously capital-and-labor-intensive work of reporting and analyzing the news.

To me, though, the overlapping sagas of First Look and The New Republic were less a dramatic climax of the zeitgeist than a slow-motion train wreck that had already ejected me through the windows and into the woods. Even as the press notices greeting these enterprises had first unspooled, I couldn’t help but hear the low moan of a gathering nemesis in the distance. Or—to switch up my entertainment metaphors—I felt increasingly like a seasoned horror movie fan, espying all the telltale signs of a disaster waiting to happen: the callow corporate rhetoric of disruptive genius, the witless embrace of a nonsensical array of platforms and formats in a sequence seemingly adapted from a Mad Libs game book, the airy dismissal of content-production as though it were simply a species of hireling grunt work.

All this had come rushing back because once upon a time, I had lived through it too, in my late, unlamented career as an online news executive in that labyrinth of high-octane managerial passive-aggression known as Yahoo News.

Into the Purple Valley

Yahoo News, it so happens, occupied center stage in the New Republic fiasco. In October 2014, a month before the whole operation went to hell, Hughes brought on Guy Vidra, a former Yahoo News higher-up, to serve as CEO of The New Republic—a position above editor Frank Foer’s in the corporate chain of command. Vidra wasted little time reminding any and all New Republic employees within earshot just what he intended to do with his power. At an all-hands gathering to divine the company’s digital future, Vidra declared that the magazine’s staff should feel empowered to “break shit”—a classic Valley exhortation that means little more than “be prepared to do whatever I say, no matter how many times I change my mind.” Fast forward a few weeks, and Vidra was pronouncing, in one of the new management team’s ineffectual, quasi-literate efforts to justify the carnage before the bar of public opinion, his “dedication to informing society and impacting the world through analysis and insight.” As he gamely tried to specify just how all this informing and impacting would transpire, Vidra appealed to the profitable precedents set by a fistful of brave new media companies in the process of subduing the Internet:

The most exciting part of the successes has been that they’ve been achieved through an array of different strategies—all of which use technology in the service of journalism—leading to more distribution and creative ways of telling stories made possible only through digital means. These publishers are growing and finding new audiences, and, while The New Republic is a very unique place, we can learn from them.

When my eyes alit on Vidra’s pronunciamiento, I recognized all the elements of a boilerplate Yahoo corporate memo: the lumbering passive voice, peculiarly unsuited to generating the boardroom-grade excitement that Yahoo memo-ists sought to convey to the working masses; the cumbersome, noun-heavy diction (somehow successes, or perhaps strategies, are telling stories, while also kicking up “more distribution,” a phrase that, on its own, says precisely nothing); the prophetic intonement of the inane as though it is, in fact, revolutionary (nothing, strictly speaking, is “made possible only through digital means,” least of all narrative journalism, which is nothing more than thinking, listening, reading, and—most ploddingly and least radically of all—writing); the effort to highlight the thuddingly obvious in the breathless rhetoric of epiphany (of course online media companies will use technology in the service of journalism because they are, ahem, media companies). And when the poor reader pans back from all this gibberish, she realizes that Vidra’s mangled subordinate clauses are really just expressing a tautology: digital media companies succeed . . . because they are digital media companies. The only measurably distinctive element of this outburst is the ungrammatical assertion that “The New Republic is a very unique place.”

The Yahoo affinities here run far deeper than the mere verbal tics of corporate groupthink. Before Hughes and Vidra had offered Foer’s job to Gabriel Snyder, they had tried to give it to Vidra’s former Yahoo colleague, Hillary Frey, the executive who presided over the constructive termination of my own perch in the Yahoo news empire. When The New Republic was on the block back in 2011, prior to the Hughes deal, there were rumors that Yahoo itself, then on one of its distressingly frequent serial media-acquisition binges, was thinking of acquiring the magazine. In a way, that outcome would have been the more merciful one: rather than going up in a fractious exchange of outraged statement and counterstatement, the old order would have been swiftly dispatched by scores of enterprising Guy Vidras. The restive spirits of past New Republic editors and contributors—Edmund Wilson, Henry Wallace, Walter Lippmann, Murray Kempton, W. H. Auden—would have been quietly chloroformed by an endless procession of PowerPoint presentations, New Economy platitudes, and buzzword-intoning conference calls.

Lost Illusions; or, Shit, Broken

But let’s back up. How, exactly, did a Baffler editor, of all people, come to serve as a Yahoo news executive in the first place?

The broad outlines would doubtless ring a bell with Chris Hughes, who’s fond of advertising his penchant for reading Balzac in French. In 2009, a year into the most crippling depression of the past seven decades, my once-stable post in the dying trade of print journalism was snatched out from under me. The venerable Hill publication Congressional Quarterly—a wildly profitable operation owned, weirdly enough, by the nonprofit Poynter Institute—was sold to a takeover team at the Economist Group. My job as senior editor for the CQ weekly magazine was among the first casualties of the austerity campaign. Our British overlords had declared that CQ’s already sizeable profit margins needed to be much wider, and so my salary, benefits, and retirement plan were all consigned to the sacred cause of padding the bottom line.

It’s an understatement to say that my professional prospects were grim. My then-wife’s employer, the liberal radio network Air America, duly went up in flames a month later. I landed a couple of interviews at some newspaper offices—places already so decimated from their own downsizing campaigns that it seemed like tumbleweeds would start blowing down the corridors of cubicles even as I anxiously tried to impress managers with my can-do spirit of innovation. As I interviewed at one of these shops, a onetime colleague of mine took me aside and advised, in a burst of hard-won gallows humor, “Listen, if you get an offer from a company that’s not bankrupt, you should probably take that.”

I took his advice. On Twitter, of all places, I came across a listing for an editing job at Yahoo, the infamous failed search engine that was now both a shuddering storehouse of legacy webmail accounts and a surprisingly potent aggregator of news content. It was unclear whether anything resembling a long-term business strategy could ever take hold at the company, but without really meaning to, Yahoo had become the most heavily trafficked news site on the web. And since the company had been fortunate enough to go public in the delirious belle epoque of the nineties tech bubble, it was overcapitalized on a truly mammoth scale. By simply selling off a software patent or two as it went, Yahoo could keep pumping cash through its great purple maw as its senior managers tried to figure out what the company was there for.

Yahoo could keep pumping cash through its purple maw as its senior managers tried to figure out what the company was there for.

Yahoo might never again revolutionize any product or platform in the crowded digital sector, but what did it matter? In an age of rapidly vanishing audiences for traditional media outlets, it had more readers than it knew what to do with. It could, like the Chicago Cubs (my longtime, and tragic, baseball fixation), continue to blow through daft management schemes and staggering market failures, and even so, through some mystic compact with its fan base, customers would stream through the turnstiles.

The Cubs analogy is especially apt in this case. Yahoo had launched a successful ring of sports blogs in the early aughts—rapidly harvesting eyeballs in this most obsessive of online communities, and drawing big-name talent away from web-averse print media competitors. The idea, I was told in a series of interviews in New York, Washington, and the editorial home office of the Yahoo news division in Santa Monica, was to replicate the sports blogs’ success in the news sphere.

Behind all this ambitious talk was a less flattering truth: Yahoo, too, was keen to curb its costs. It had partnership contracts with several high-profile media companies, all of which were delighted to see their product dragged in front of millions of Yahoo-branded eyeballs. But as their print clientele abandoned them, these companies also sought to pad their own sagging bottom lines by hiking up their licensing fees and charging Yahoo more. Emboldened by the success of the sports blog network, Yahoo executives figured they could produce news product far more cheaply in house. After all, they already had, in spades, the main asset that the rest of the mediasphere was starved for: readers. All they needed now was a team of enterprising reporters and editors to keep daily, and hourly, content buzzing through the company’s outsized distribution system.

That’s where I came in. I was hired in an overheated blur of Silicon Valley hype. My formal job offer came packaged in a FedEx box that had been rigged up to deliver the company’s irksome trademark soprano “Yahoo” each time you opened it. Even after I rushed it into my kitchen trash can, it would start in on its infernal yodeling loop whenever I’d discard a used yogurt carton or wadded-up paper towel on top. It was the branding mechanism that would not die.

A related ominous portent, as I discovered upon opening my big purple yodeling box, was that the company’s HR team had adopted the cutesy-to-them tic of referring to employees simply as “Yahoos”—making us seem either like backwoods rubes or (to more literary-minded hires) the ravenous creatures in Gulliver’s Travels who manage to combine both elitism and boorishness, digging through the muck to retrieve jealously hoarded precious stones. Here, too, was a parable in miniature: Yahoo, the company, clearly was keen to have me adopt the classic Swiftian version of the Yahoo identity. Meanwhile, the career path unfolding before me would soon transform me into the considerably less distinguished, and infinitely more gullible, variety of (decidedly lowercase) yahoo.

But all that was to come. The task ahead was to hire and put to work a new crew of news bloggers, covering everything from media and foreign policy to finance and national politics. My immediate boss had the title of managing editor for the fledgling blog network, but had never previously worked as an editor. (He was and is, let the record show, a very accomplished publisher and news manager.) So the day-to-day hiring and supervision of the news blog team fell largely to me.

The numbers alone were staggering. Anytime one of my team’s posts landed on the Yahoo homepage, it could easily rack up several million unique pageviews, sometimes in a matter of hours. Also-ran posts, such as daily news roundups or procedural updates on the then-burning issue of health care reform, would usually plateau in the low six figures. CQ, New York magazine, the Washington Post—any of the media name brands I’d previously worked for, or could ever reasonably hope to work for—would have killed to attract the volume of readers earned by a post that the Yahoo news team would see as a failure.

There were other attractions to the job, too, beyond the obvious inducements of a salary and a health plan. After a long tour in the ultra-earnest word factory of CQ (which had deemed the word “reform” itself too controversial and loaded a term to mar our bloodless copy), the tabloid sensibility that drove the high-performing content at Yahoo was oddly liberating. We were ensured seven-figure viewerships for reports on any and all subjects calculated to tickle a web user’s idle curiosity, from cheeky music videos put together by U.S. troops stationed in Afghanistan to a global competition to identify the hottest new strain of chili pepper. Anything bearing the imprint of culture-war controversy or celebrity gossip rapidly shot up the pageview boards. One of the all-time traffic leaders was a post on a lesbian high school student denied admission to her senior prom when she turned up with a same-sex date; that entry netted more than sixty thousand reader comments.

On one early morning conference call, I blearily pitched an oddball story I’d seen about Today Show host Ann Curry; while delivering a college commencement address, she had clumsily referenced the history of another college of the same name throughout. The ensuing post dislodged the Alabama prom drama in the annals of high-volume traffic and drew so many pageviews that the editorial team took to using “an Ann Curry post” as shorthand for a big win for the site. By randomly stumbling across the tale of a minor TV personality’s public embarrassment, I had sealed my reputation for online news savvy. (Welcome to American journalism in the twenty-first century.)

In the space between the front-page tabloid fare and the back-end site filler, though, we were given a surprising amount of leeway. The ultimate motives of Yahoo’s news managers may have been base—like those of news managers everywhere in our blighted age—but the company also seemed to be genuinely committed to the sustained, reasonably adventurous promulgation of useful information on the web.

What’s more, the middle managers who moved copy on and off the front-page portal fought to ensure that Yahoo stories were both topical and accurate. I was able to publish in-depth explainers on the Dodd-Frank financial reform initiative, the tangled course of the Affordable Care Act, and the wigged-out antigovernment delusions of Gabby Giffords’s would-be assassin Jared Loughner. My reporting team did important and groundbreaking work on everything from the 2010 Deepwater Horizon oil spill—our reporter moved down to New Orleans from New York, on his own dime, to cover it—to the impact of Arizona’s draconian new immigration law to the Tea Party’s dramatic rise in the 2010 election cycle.

To my great surprise, some of the most demanding, information-rich features we assembled earned us major traffic on the homepage. A post on widespread public opposition to the Supreme Court’s Citizens United ruling—a ruling that effectively repealed most reasonable restraints on money in politics—drew pageviews in the millions, as did a similarly grim set of charts driving home the ensuing boom of dark money in national politics (thanks in part to the editors of Mother Jones, who graciously let us adapt them). Yahoo readers clearly loved to be titillated, but they also didn’t mind sobering updates on the rickety state of our formal democracy.

One especially ambitious project was a multipart, crowdsourced account of the rigors of long-term unemployment in the job-starved “recovery” from the 2008 meltdown. Not knowing what to do with all the material we’d transcribed from tens of thousands of contributors to the series, we created a Tumblr devoted to the project, which we updated independently of the daily pull-and-push of the Yahoo News homepage. I still recall being on a conference call with a gaggle of with-it digital news managers trying to explain to them just what Tumblr was, as I fought to tamp down a growing suspicion that something was very, very wrong. Two years later, of course, Yahoo added Tumblr to its long, and largely inert, roster of media acquisitions, for a cool $1.1 billion.

Dumb Money

That bracing little set piece sums up a great deal about what ailed Yahoo in the inner reaches of its corporate being: a perennially addled (and ever-shifting) team of managers with far too much money to burn and virtually no restraints on how they might choose, at a moment’s notice, to radically reconfigure the business rationales animating Yahoo News. As our hardy band of news bloggers plowed through the challenges of daily reporting, we found ourselves pushing farther into the treacherous, bottomless deeps of corporate groupthink, much like the doomed Jedi pilots barreling into the canyons of the Death Star in the final reel of the first Star Wars movie.

First, there was the rotating cast of executives. Yahoo being a company of nineteen thousand employees (in the spring of 2010, when I was hired) across the globe, there were many, many bosses, strewn across many recondite corporate divisions, all of whom could mysteriously be summoned onto the same conference call within minutes.

I wrote a post marking our one-billionth—yes, that’s billion, with a b—pageview.

Then there was the company’s strange aversion to the most basic canons of newsmaking. Soon after I landed at Yahoo, I realized that my central job duties didn’t fit into the tech-centric template that the company favored. The Yahoo hierarchs shared something of a company-wide allergy to the inoffensive “editor” descriptor. Our main news authorities in Santa Monica were called “producers” instead; their tasks were tethered mainly to the portal they served, as opposed to the readily transferable old-media work of reporting, writing, editing, and proofreading. You could be a front-page producer, or a facilitator of partnered content, or a sponsorship wrangler, but plain old editors and writers were almost nowhere to be found. One of the lead producers in Santa Monica was exclusively tasked with running down the rights and proper web formatting for video footage. (Lest that sound like a make-work gig, akin to the character in Galaxy Quest who does nothing but convey the crew leader’s instructions to the ship’s computer, rest assured that videos were among the most heavily trafficked, and jealously guarded, features on the site; this producer was also among the handful of Santa Monica senior brass who’d logged time as a working journalist.)

And then there were the algorithms. Like all tech leviathans, Yahoo believed it could reduce almost anything—news consumption not excluded—to a data set. The company’s army of software engineers had designed a customization feature on the Yahoo homepage called CORE: the “content optimization and relevance engine,” for you connoisseurs of tech industry agitprop. The idea behind CORE was to take the data Yahoo had collected from its registered users and develop algorithms that would accurately predict what stories would provoke site visitors to click, linger, and read, as a steady barrage of revenue-generating ads nudged themselves into the margins of their experiences. In its first year of operation, CORE proved to be a phenomenal success, netting a 270 percent increase in pageviews.

The big problem with a project like CORE, of course, was that it was pretty much antithetical to journalism as a civic activity. The always more-than-a-little mythical image of American news readers as informed citizens rests precisely upon the news being unfamiliar to them—and indeed, on all too many occasions, shocking, scandalous, and enraging. To lovingly “curate”—as the IT term of art goes—a version of current events to mirror readers’ hobbies, taste preferences, and browsing histories is to downgrade journalism into the stuff of Pinterest posting—strangely pleasing in many cases, like a warm bath for an infant, but serving no larger civic good. In another telling turn of phrase, front-page producers would talk of “forcing” stories that defied the counsel of the CORE algorithms—usually breaking news in the world of politics, policy, and global affairs—into placement on the front page. In other words, the independent exercise of news judgment, in this code-happy universe, was regarded as a willful lurch into manual-override mode. And even when a story was “forced,” if the click-count didn’t spike, it was quickly banished to the nether regions of the site, so the algorithms could resume their seamless work of optimized news sorting and placement.

Small wonder, in this strategically cloistered news environment, that the director of the news division’s main tasks were to negotiate contracts with partner companies and to consult with us on any news coverage that might involve potential conflicts of interest for the company. He was an entertainment lawyer, and had come to Yahoo from the even more distressed and revenue-challenged confines of the music industry.

The fussy terminological diffidence that turned editing into a dirty word betrayed a deeper unease atop the Yahoo hierarchy. Company executives would get unnerved by the unpredictable character of the news itself, should it stray too far beyond the familiar canons of optimal CORE placement. The independent conduct of journalism was often greeted with faux market-savvy suspicion; how could a giant news aggregator assess material that hadn’t been pre-vetted by a duly contracted content partner?

One of the first pieces I reported for the site concerned the tactic, favored among some militia groups, of committing crimes in order to ambush law enforcement personnel. Before the post went live, I fielded an anxious phone call from a senior manager in Santa Monica. He was alarmed that we were reporting on this practice for a simple reason: “I haven’t heard of this before.” I struggled to find a diplomatic way to explain that publishing things that readers hadn’t heard before was something that a news organization should be doing a whole lot more of: it was, in fact, the definition of “news.”

But news and its safekeeping were concepts that the Yahoo management corps would find difficult to digest throughout my tenure, and it showed in the operation’s basic infrastructure. A separate Yahoo bureau in Washington, D.C., where I was based, was initially focused on financial coverage—a beat that made little sense some 250 miles south of Wall Street, and even less sense if you considered that the recently designated D.C. bureau chief still maintained a principal residence in New York.

Stranger still, the D.C. bureau was initially housed in the company’s lobbying offices, in a famous high-rise office building devoted to influence-peddling directly across from the U.S. Capitol. The notorious, insanely pricey Charlie Palmer steakhouse, where industry flacks romance lawmakers just beyond the ambit of federal lobbying strictures, was on the ground floor. If you happened into the wrong office space while visiting the D.C. bureau (as I usually did, since I worked from home—this was long before Marissa Mayer took control of the company and deemed telecommuting a hazardous drain on Yahoo’s resources and general morale), you’d stumble across a cache of Yahoo-branded coffee mugs or mousepads intended to fill out gift bags at this or that tech-industry reception.

It was hard, amid such glaring reminders of the company’s true corporate mission, to feel like you were anything more than glorified party swag yourself. What we were doing in the news division added value to Yahoo’s brand, to be sure. But we understood all too well that just as easily as we had sprung into being to forestall continual fee increases from partner companies, we could be stripped down and sold for spare parts—or worse, left to languish in the backwaters of Yahoo’s sprawling global bureaucracy.

That’s Entertainment!

This latter fate in particular preyed on our minds, since it was already overtaking another of the company’s blog startup projects. Yahoo was planning to debut a ring of arts and entertainment blogs, and had hired a dozen or so well-established digital journalists to cover movies, TV, digital culture, and publishing. But as it turned out, the site would never get off the ground—instead, it stalled in beta development for more than a year.

While high-stakes corporate intrigue over the entertainment project raged out West, the property’s entertainment bloggers became steadily more restive, bored, and angry. They suffered all the small-bore indignities of daily blog work—covering dubiously newsworthy developments in their field and manufacturing click-baity takes on this or that meaningless popcult trend or product in order to drive traffic—but in a complete vacuum.

It was like an especially cruel lab experiment, depriving rats of sustenance and social recognition until they started tearing at their own flesh. Everyone was being paid reasonably well, but each day they generated a full menu of content for a site that didn’t exist, setting out to titillate, engage, and inform readers who never showed up. A friend who was hired into this Beckett-like simulacrum of a journalism shop told me that he staved off the ennui of the job by knocking off early most afternoons to go swim at the Y for hours on end. It felt like a small blow for self-respect to get healthy, if nothing else, on the company’s dime.

Soon, it all came crashing down for the entertainment blogs in typical Yahoo fashion. Without any notice, a division chief in Santa Monica pulled the plug; word had it that she had never liked the project, and felt that it ran at cross purposes with Yahoo’s weirdly essentialist “women’s interest” portal, whose lackluster editorial mission was neatly summed up by its blindingly chipper name, Shine.

Company veterans readily grasped the real problem here: Because the entertainment site would, like its news counterpart, traffic in its own reporting and criticism, it would fit awkwardly alongside the boosterish product featured on Shine. And in the worst-case scenario, should it succeed on anything like the scale that our news sites had, it would make Shine look even more like the obliging waystation for repurposed PR copy that it was rapidly becoming. Shine would, therefore, gleam on, while the entertainment blogs went abruptly dark (or more precisely, their chronic darkness became a permanent condition), right around the Christmas holidays. My counterpart who’d been editing and supervising the launch was preparing to have a baby and go on maternity leave at the time; she at least won a fairly generous buyout, albeit one that came with the hidden cost of a nondisparagement clause.

Over at the news blogs, meanwhile, we kept nervously piling up the pageviews. Our 2010 election coverage netted huge traffic, as did our treatment of big breaking news stories, like the Japanese tsunami and the killing of Osama bin Laden. On the site’s first anniversary, I wrote a post marking our one-billionth—yes, that’s billion, with a b—pageview, and surveyed our achievements with not-unreasonable pride.

Still, we began to experience our own issues with the Santa Monica brain trust. At first, Yahoo’s executive-suite dysfunction looked as though it might work to our advantage. Within the space of a month, my immediate supervisor fled for another job in television; I got promoted to replace him, which meant, on paper at least, that the blog and I would be sitting securely, if not exactly pretty, within the managerial maw of the purple behemoth. I would be reporting directly to the deal-cutting news director out West, who greatly appreciated the ways in which our native content had simplified his hardball negotiations with content providers. I would—again, on paper—be able to hire on a political team to begin covering the fast-approaching 2012 presidential election cycle.

This balmy sense of provisional well-being proved short lived: the glorified snakes-and-ladders game that would soon establish itself as the all but perpetual status quo in the C-suites of Santa Monica was only just getting under way. First, my brand-new editorial protector in Santa Monica suddenly hit the bricks, taking a more congenial deal-making post at Disney. Big company players likewise checked out at several layers of management above him; at one point, on a phone call with a senior manager on the East Coast, we did the math and realized that the closest thing to a clearly defined superior we had was the company’s interim CEO, off in Yahoo’s hulking corporate mothership in downtown Sunnyvale.

Not that Sunnyvale was looking all that more secure. The company’s maximum leader, a gratifyingly foul-mouthed woman named Carol Bartz, had been given the heave-ho via phone (you stay classy, Yahoo!) after the company board decided that their stock was underperforming, even by Yahoo standards. No one yet knew who would succeed her, and I had to jury-rig a set of temporary fixes as I went down my list of urgent needs, from bringing on new correspondents to cover the 2012 election to getting full-time benefits for our blog team, who had all initially come on, Walmart style, as just-shy-of-fulltime contract workers, strategically ineligible for health care. (All together now: You stay classy, Yahoo!) At the end of one especially anguished call with the aforementioned, infinitely patient East Coast manager, I told him that I was going to hire at least one new political reporter, to cover the burgeoning GOP primary field, unless he did something to stop me. He didn’t, and I did. So, with tremulously mounting confidence, I could say I was overseeing an actual election “team”—i.e., three reporters, as opposed to a harried and overworked duo.

America: Don’t Ask

Unfortunately, Santa Monica, too, was slowly realizing that a major election cycle was on the way. An enterprising soul in senior management there had me draw up a long series of memos outlining our election game plan. I also got dragooned into advising him on a half-hearted bid to launch still another informal blog franchise, this one devoted to opinion journalism around the election. It was here that things started to get truly unnerving. Conference call after conference call ate into my workday, and so far as I could see, this project—which bore the vaguely “Shine”-like sobriquet “Voices”—was on track to join the entertainment startup on Yahoo’s island of lost blog toys.

I was regarded as a doomsaying, old-media scold at the great digital cross-branding banquet.

The moment of reckoning appeared nigh when the Santa Monica schemer presented me with an elaborate PowerPoint laying out his, uh, vision for Voices. The first slide offered the familiar toy-soldier pairing of left pundit and right pundit; the arrangement was made to look vaguely dynamic only by virtue of being formatted as a flow chart. But something more than just the hackneyed muscle memory of cable news production was amiss here. In the right quadrant of the flow chart, in excitable all caps, was the name of the Beltway right’s self-styled “prince of darkness,” Robert Novak. The problem was that by this time, Novak had been dead for two years. In the same measured tones in which I was earlier obliged to parse out the concept of news, I now explained that, while it would indeed be a major coup to land Bob Novak for this project, the move would not result in—how shall I put this?—very lively prose.

It got worse. The consensus pet election project back West turned out to be something called Remake America. This was essentially an updated video-based version of Ask America, a failed Yahoo gimmick from 2010. The idea back then had been to harness Yahoo’s central asset—its gargantuan online readership—as a reporting tool. We were to be tasked with converting our enormous online following into policy advisers without portfolio. We would petition them with questions about their political priorities, and they would, one diligent web user at a time, help the American republic stir out of its forbidding post-2008 slough of despond.

There were a few problems with this notion. First off, Yahoo readers, like online readers everywhere, were prone to erecting enormous, vituperative flame threads out of nothing at all. Putting this group of choleric and self-dramatizing personalities in charge of the country’s policy priorities was a bit like entrusting negotiations for a global carbon-emissions treaty to the Koch brothers.

Second, by far the most vocal Yahoo commenters were the most dogmatically racist; we’d joke grimly that a Yahoo commenter certificate had to be a complimentary gift to every newly enrolled member of the Klan. Seasoned front-page programmers knew that anytime we published anything touching on race relations in America, the first order of business was to disable comments on the post before it went live. Likewise, the mood among front-page programmers never got more frantic than on the occasions when we managed to push out a post that even mildly challenged the Confederate mindset with the comments still enabled.

To make matters worse, since topical reasoning was not the strong suit of this energized commentariat, its members would occasionally descend on a completely unrelated post en masse and smear it with thousands of imbecilic racist outbursts. On one unfortunate occasion, this happened to one of our posts, and before we could reverse engineer our way out of the hate-fest, the CMS system seized up; we couldn’t shut off the comments, and we couldn’t delete the post. For weeks on end, it just sat there, oozing ugly misspelled racist obscenities and brutally mocking the high-flown civic conceits of let’s-put-on-a-show digital interactivity.

Ask America, in short, was to tank well before we could get America to cough out a coherent reply. In the blog trenches, we coined a new name for the project: “America: Don’t Ask.”

Remake/Remodel

But the dream of interactivity dies hard at a company with a gargantuan readership and no clear business plan. Even as it became obvious that Ask America would gain zero traction among our readers, the company’s PR team chugged aimlessly along, dispatching a clutch of Ask America–branded trucks, stuffed no doubt with yet more purple-hued Yahoo swag, to college campuses and hipster neighborhoods across the country. When that didn’t work, they would try again, two years later.

Hence Remake America, which sought to recast its America-probing antecedent as a high-concept, and closely micromanaged, Frank Luntz–style focus group. Since it was clear that we couldn’t just throw open the floor to the more, well, yahoo elements of the Yahoo nation, the overlords of Santa Monica elected to retain maximum filtering power over just who would represent America, and how. The idea now was to recruit a group of “ordinary” Americans to supply running commentary on the election in a series of video diaries. It would be a walking, talking cross-section of the American public: a struggling small-business owner in the upper South, a Missouri veteran trying to support his family while recovering from war injuries, and so on. In reality, of course, this was a fantasy projection—what the give-and-take of a presidential campaign would look like if a clutch of Yahoo executives were charged with casting and scripting it.

It was also, of course, anything but journalism. The voters and families taking part in Remake America were carefully screened and coached by roving teams of producers and videographers, so that their responses to political events were just about as real and spontaneous as the drunken hookups on Jersey Shore. The eyeball barons in California may have been diffident about editing, but they sure could stunt-cast.

In a series of conference calls and face-to-face meetings, I made it clear that my crew of news bloggers would have nothing to do with the project—and that I viewed it as self-promotional news-branding gone off the rails. I suggested that the producers choreographing the effort might do well to consult Albert Brooks’s prescient seventies takedown of the documentary-verite style, Real Life,or the great James L. Brooks journalism morality play, Broadcast News. Yahoo’s top brass honored my plea to quarantine the news blog team from the overheated doings at Remake America—but it was becoming increasingly clear that I was regarded as a doomsaying, old-media scold at the great digital cross-branding banquet.

As part of a new partnership with ABC News, Remake America was briefly plastered across daytime television. But it, too, ingloriously expired after election day. America declined to be remade in much the same way it had shunned being asked: interrogate it or prod it as we may, the country just sat there. (Taking a somewhat more cynical view of things, one could hardly blame it. America was initially asked, and when it didn’t yield satisfactory replies, it was to be remade; Yahoo’s relationship with its host nation, like that with its workforce, followed the queasy script of battered spouse syndrome.) Today, any search for the project’s content on Yahoo just directs you back to the news homepage; even in death, Remake America is desperately trying to get you to mistake it for news.

In the meantime, other changes were afoot. The long-vacant management slots separating me from the CEO empyrean were at last getting filled, with executives from TV, business journalism, and successful Internet startups. Synergy abounded. TV studios sprouted under the aegis of the New York office, and we teamed up with ABC’s political division to host liveblogs and webcasts for presidential debates and primary nights.

This was all well and good, but it lacked a certain visionary élan. If Yahoo was going to become a true digital news brand, it would have to go on a major innovation binge—it’d have to start “breaking shit,” in other words. One senior news executive exulted that Yahoo News was in the most enviable position that any media company could be—it was a startup, he’d intone, that already had the largest readership on the web. This, too, was classic Yahoo corporate boilerplate: it sounded vaguely pulse-pounding when shouted above a PowerPoint stream, but on closer examination, it made no sense whatsoever. Precisely because it already commanded the largest readership, Yahoo couldn’t be a startup. Startups thrive on investor bets made on the promise of future profitability and, over the course of their initial runs, are case studies in capital destruction; far from ascending to Yahoo-scale market dominance, they’re expected to rapidly burn through their initial investment stakes en route to attracting more and bigger investors. For Yahoo to be a genuine startup, it would have to utterly fail at being Yahoo.

Very much by contrast, Yahoo was a lead investor in digital enterprises. It didn’t develop bold new tech properties—it merely acquired them. The company’s main claim to profitability has been the mountain of shares it was able to flip when the Chinese online shopping giant Alibaba went public. (True to form, Yahoo declined to float its enormous Alibaba winnings to fund a bold or entrepreneurial bid to revolutionize the web; instead, it spun them off into the guardianship of a dummy corporation, so as to save the company billions in tax liabilities from the Alibaba IPO.) To goad its lead executives into startup mode would be like expecting the lead actors in The Sopranos to run a marathon without notice. Far from offering the best of all possible worlds, as its chief Santa Monica cheerleader insisted, this managerial conception of the news division’s pseudo-startup mission offered the worst. It wouldn’t add anything to our already strained reporting and editing capacity. The news sites had laid off their only two fulltime copyeditors in an earlier round of staff cuts, and never bothered to replace them; why copyedit, after all, when you can break shit? That lustily intoned startup mantra, I knew, was certain to continue sanctioning colossal wastes of resources and effort like Remake America. Let a thousand videographers bloom!

As I took in all the way-new management-speak sprouting up around me, my own corporate redundancy was mercifully taking shape behind the scenes. In the waning days of 2011, an energetic Santa Monica kingpin requested that I sit in on a conference call; the subject line of his email request simply read “2012,” which led me to assume that we’d be discussing election-coverage plans.

Instead, I was informed that my job had been completely overhauled—and stripped of most of its critical responsibilities. Our new director of politics coverage was to be my deputy, working out of New York, while down in D.C., I would, absurdly, be expected to ignore national politics and the Washington bureau I had hired and supervised. Instead, I would be captaining coverage of “national and global affairs.” Poor Yahoo; even in its bid to banish me from its election-year lovefest of media platforms, the company was betraying yet again its cursory attention to the basic spadework of beat delineation: to supervise coverage of “national and global affairs” was to be in charge of everything.

Or nothing, as the case may be. There was no mistaking that this redefinition of my job duties, however lamely the new management team tried to dress it up, amounted to the constructive termination of someone who was turning out to be less and less of a team player. I told them I’d consider the reconfigured post, and after I had, a few days later, I wrote in to submit my resignation. During the long fortnight during which I served out my notice, similarly dispirited colleagues told me that the mastermind of my corporate repurposing—the same jaunty soul who longed to conjure Bob Novak back from the dead—was crowing that he had “blown up” Yahoo News. Shit, once again, was broken.

Conflicts Without Interest

The smarmy Silicon Valley vacuity of the phrase aside, the notion that I and my blog team had been “blown up” always struck me as more than a little melodramatic. Nothing ever blows up at Yahoo—unless it’s a lurid tabloid listicle or a racist comment thread. Absorption, not combustion, is always the order of the day.

It thus came as no surprise that, after my departure, the company went on a celebrity hiring spree, snapping up industry personages to be nominal editorial leaders of its most ad-friendly verticals. Cosmetics mogul Bobbi Brown took over as editor in chief of Yahoo’s beauty site last spring. (Yes, even though Yahoo is now getting comfortable with the term editor, the company clearly still doesn’t have a clue what it means.) David Pogue, a former New York Times digital-gadget correspondent so thoroughly in the tank for his industry that he actually married one of its PR executives, was welcomed with open arms in 2013; Yahoo’s maximum leaders lauded him as a perfect specimen of synergistic tech coverage.

Leading this revolting charge is Marissa Mayer, the former Google executive brought on to captain the company in 2012, after its previous Silicon Valley CEO recruit, former PayPal honcho Scott Thompson, was found to have faked his college credentials on his résumé. Mayer is now banking on an overtly corrupt model of digital journalism to help stanch Yahoo’s steady hemorrhage of ad revenue. Significantly, one of her right-hand men in consolidating this market-prostrate vision was the jargon-barking mogul-in-waiting Guy Vidra, who rose from captaining the company’s vague “news strategy” efforts to overseeing all of Yahoo’s news operations.

Mayer’s new synergistic vision yielded quick dividends. What Mayer is pleased to call the site’s stable of “digital magazines” is, in reality, the barest of fig leaves for an orgy of sponsored content—i.e., copy commissioned, inspected, and (increasingly) edited by advertisers, and misleadingly packaged as reliable, independent journalism in order to win eyeballs and reader trust. (A collateral casualty of this campaign, oddly enough, was the women’s site Shine, which was deemed insufficiently innovative, even though it remained one of the few revenue-earning stalwarts of the Yahoo media empire.) Under Mayer’s leadership, the company has brought this ugly art form to sophisticated new heights—and in the process blown through all the basic rudiments of journalistic ethics. Behold New York Times reporter Vindu Goel’s account of the unsightly new effort to repackage a craven old-media sin:

Built using technology acquired last year as part of the company’s $1.1 billion purchase of Tumblr, the new publications combine original articles and material licensed from other sites, as well as big photos and videos, into an endless page of titles aimed at enticing people to linger. Mixed into that stream is a different kind of advertising—so-called native ads or sponsored posts—which look almost exactly like all the other articles and videos on the page except that they are sponsored by brands like Knorr, Best Buy, and Ford Motor. These ads, Yahoo hopes, will attract the attention of more readers and make more money for the company. In some cases, Yahoo editors even help to write that advertising—a blurring of the traditional lines between journalists and the moneymaking side of the business.

Indeed, Goel’s dispatch features Yahoo digital magazine editors trying to one-up each other in formulating ad-friendly content strategies and tying themselves up into incoherent knots as they desperately try to rationalize their permanent state of market prostration. “I think that our involvement elevates the advertising,” Sarah McColl, the erstwhile editor in chief of Yahoo Food, told the Times. “Our ability to bring editorial knowledge and finesse to advertising content makes it better and gives it a point of view.” No, actually: when editorial knowledge is deployed to elevate advertising, it stops being either editorial, or knowledge; it’s hackery, sold out to the highest, or just the bare middling, bidder.

If Yahoo was going to become a true digital news brand, it’d have to start “breaking shit.”

For an edifying look at how this editorial outlook affects hitherto uncompromised and independent journalism, ponder the gruesome tale of Yahoo-enabled corporate prior restraint recently reported by Deadspin’s Kevin Draper. Mayer’s editorial deputy, Kathy Savitt, went into heads-must-roll conniptions when she learned that Yahoo Sports NBA blogger Kelly Dwyer made passing reference to Cleveland Cavaliers owner Dan Gilbert’s career as a predatory lending baron as CEO of Quicken Loans. Just days before, Yahoo had entered into a lucrative partnership with Gilbert’s company to produce an inane NCAA March Madness bracket competition. Yahoo sources told Draper that Savitt began loudly demanding that Dwyer be fired for his revenue-threatening thought crime; and while she was evidently talked down from that ludicrous demand, she did proceed, at Gilbert’s vainglorious urging, to scrub Dwyer’s modest blog post from both the site and Yahoo’s searching functionalities. This obsequious brand of synergy speaks volumes about Yahoo’s recent devolution. Not only does it involve the once-respected sports blog network that was meant to serve as the model for the company’s news division, but much more to the point, Savitt had precisely zero background and training in journalism, apart from a stint thirty years before at her college newspaper. Mayer, in her infinite market-prostrate wisdom, merely added all of Yahoo’s editorial operations to Savitt’s bailiwick as marketing director—because, you see, that’s just how Yahoo rolls.

Yahoo’s present, blinding moment of self-devouring synergy is but the logical culmination of all the counter-journalistic practices that so transfixed company management during my tenure there. And what this process portends is only too clear. For all the clumsy rhetorical lip service Guy Vidra pays to The New Republic’s hallowed intellectual traditions, this is what his vision of a nimble digital news product finally translates into: a vaguely journalistic veneer strategically designed to conceal a rancid interior of “elevated” advertising. This, among countless other reasons, was why one could never make the case for sustaining a stable culture of reporting and editing at Yahoo News. At one bygone conclave of the Yahoo managerial elite, a colleague of mine tried to stress the need to redouble our commitment to our existing model of independent newsgathering, and his plea only earned him this spiteful rejoinder from a fast-talking Santa Monica power broker: “Past is prologue.”

Perhaps, but when all present trends are converging toward the thoughtless downscaling of editorial work into a bonus accessory in a client’s advertising account, the past had better make a deeper impression. The scrupulous separation of business and reporting mandates, and the pride of journalistic craft necessary to effectively police that separation, are no doubt old-media traditions, but they became old for a reason.

Mixology

And not surprisingly, when you contemptuously muscle these traditions aside, you get a media company that only plunges more deeply into its own self-inflicted identity crisis. Where Yahoo executives might be rewarding grown-up journalists for grown-up journalistic work, they instead corral them together to play-act bit parts for Yahoo-branded spectacles-on-demand. So it came to pass that, amid the blizzard of horrific news otherwise known as the 2014 election cycle, I came across an invitation to a Yahoo event called the Midterm Mixer, to be convened at the Capitol Lounge, a D.C. nightspot.

The event’s jaunty moniker perfectly captured the careless, slapdash worldview of the producers who confected it. Hosted by network news also-ran Katie Couric (who has recently signed on as Yahoo’s “global anchor”), the mixer promised little enough in the way of furtive ruling-class mating rituals; instead, it was a veritable Grand Guignol of misguided synergy. David Gregory, the recently deposed host of NBC’s Meet the Press, was to be on hand, presumably to make Couric’s descent into election night maître d’ duty appear dignified, at least by comparison.

There was to be, of course, the cable-mandated presentation of matched major-party mouthpieces: Leslie Sanchez for Team R and Jamal Simmons for Team D. For depth and context, there was a similarly yoked pair of institutional apparatchiks: longtime antitax and antigovernment activist Grover Norquist, the leader of Americans for Tax Reform, on the right; and on the left, think tank honcho Neera Tanden, of the White House–osculating Center for American Progress. Politico White House correspondent Mike Allen—the hack’s hack of D.C.’s bloated and braindead journalism scene—would also be in attendance, evidently to serve as a kind of Cheshire Cat mascot at this most Washington sort of (lowercase) tea party.

The 2014 midterms were in many ways a landmark ballot, forcing sustained and wrenching reappraisals of reigning assumptions about how our major parties approach the basic work of attracting (and, all too often, repelling) key blocs of voters. But none of this was deemed suitable fodder for the Yahoo barroom display. Indeed, all that the event managed to conjure in the way of actual journalism was the totemic whiff of hard liquor itself—and even that felt cheap and unearned. The real-time election-night coverage on Yahoo resembled nothing so much as a directionless piece of performance art in which the self-conscious players gradually succumb to their most disabling fear—that they are performing before a cavernously vacant civic house. Like much Yahoo-branded activity toward the end of my tenure there, the Midterm Mixer generated a great deal of social-media hype, and probably more than its share of pageviews. But none of the activity chronicled on the page was memorable, insightful, or remotely informative.

And yet, like the clumsily interred remains of Remake America, the vacant spectacle has soldiered bravely on. As I type these words, in mid-November, the Yahoo homepage features Katie Couric’s breathless video promo trailer for the mixer event—featuring a Twitter-sponsored photo booth and a performance by the Georgetown Chimes, an a cappella combo of painfully white undergrads clad in power suits—sandwiched between two other messy, though eloquent, specimens of content synergy in our time: David Pogue, informing us that Microsoft’s Taylorite new “fitness band” is simply “beautiful . . . on the inside,” and Bobbi Brown, divulging the secret behind “Smoky Eyes for Glasses.” The legend above reads “Only on Yahoo.” Thanks to the likes of Guy Vidra and Chris Hughes, we can no longer console ourselves with the hope that it shall remain ever thus.