Maer Roshan.

On or around April 5, a group of prominent New Yorkers—including Andre Balazs, Gwyneth Paltrow, Lindsay Lohan and Harvey Weinstein—received a curious group text.

It was from Courtney Love, and she was pissed. Maer Roshan, she said, was fucking unethical. He was not to be trusted. He’d secretly tape recorded her, she claimed, and sold her out to the Internet.

What had prompted Ms. Love’s fury was a rambling video that had been posted by Mr. Roshan’s recently launched website, The Fix, in which Ms. Love assailed Kelly Osbourne for calling her a crackhead on the E! Channel. “I’ve saved her life twice, physically,” Ms. Love fumed on camera. “Booze, Oxycontin and coke—foaming at the mouth … ”

A number of online outlets had immediately picked up the story. And since it was evident to any of the hundreds of thousands of viewers of the clip that it had clearly been recorded with Ms. Love’s full knowledge and consent, Mr. Roshan confronted her the next day. She replied via text. “I’m very sorryed,” she wrote. “Just Fuckkked upp. Hate the stuupid innternet. Want to hang out tonite?”

Did we mention this website is focused on sobriety?

I witnessed Mr. Roshan extinguishing any number of such flare-ups firsthand, back when I worked as executive editor of Radar, the energetic, endearingly scattershot magazine and website (I say without prejudice) that he launched to great fanfare in 2003 and then stuck with through one mercurial billionaire backer after another.

The new website marked a comeback for the editor, who’d watched helplessly as Radar’s backers sold the property out from under him in late 2008. The demise of the magazine had been brutal. At the end, he often seemed red-eyed and exhausted. And then we all packed up our boxes, and he disappeared. For a while, stories made the rounds among friends and colleagues (TV projects, big Web editing gigs), and then they didn’t. Anybody heard from Maer?

As it happens, The Fix’s subject matter was not chosen at random. Mr. Roshan had developed a serious drinking problem while struggling to launch and to then relaunch Radar and spent a good part of the past two years drying out in various rehabs, halfway houses and sober-living facilities.

A pricey treatment program “with trust-fund kids and rich celebrity people,” as he put it, didn’t do him much good. Eventually, he wound up at a rehab called Cri-Help, where the accommodations were spartan and many of the clients had arrived straight from jail. “It was in the Valley,” he noted meaningfully. “Need I say more?”

Mr. Roshan was standing in front of a crowded tea shop not far from his apartment off Union Square, smoking a cigarette. He was wearing a light gray shirt open to the third button, black pants and black woolen overcoat. He looked much better than when I’d seen him last—thinner, healthier, more bubbly—though a notably round pot belly persisted.

One of his bunkmates was a skinhead, “a swastikaed young gentleman,” he said, named Jared. “Of course, he was delighted to learn that his roommate was this gay Jew. And yet we ended up getting along really well! Except I really didn’t like his music.”

The experience doesn’t seem to have affected Mr. Roshan’s mischievous sense of humor, at least, not to judge by The Fix, a sobriety site as only he would conceive it. Along with rehab reviews, various resources for people seeking help, and hard-hitting pieces by the likes of Susan Cheever and Chris Byron, the site runs more unlikely stories, such as “AA’s Most Annoying Cliches” and “The Argument Against Abstinence.” And then there’s Ms. Love, listed among The Fix's “hand-picked pros,” who maintains she’s been sober for years, even while admitting to the occasional sip of rosé or bump of coke.

Whether The Fix—which can sometimes seem jaw-droppingly lighthearted—effectively promotes sobriety for its readers (or for its editors) isn’t entirely clear. Debates on the subject rage in the comment forums. But nobody who’s followed Mr. Roshan’s extraordinary whirl on the media thrill ride is surprised by The Fix’s nervy tone. Twenty years ago, as the 24-year-old editor of a short-lived gay weekly called QW, he outed right-wing icon Phyllis Schlafly’s son John. The story was picked up nationally and led to Mr. Roshan’s denunciation by the family-values crusader on Meet the Press. His 1997 New York magazine cover story “Trophy Boys,” co-written with Eric Konigsberg, about a cadre of attractive young “male courtesans … living in higher style than Andrew Cunanan ever imagined,” prompted angry letters from David Geffen and finance writer Andrew Tobias and seems to have been scrubbed from the magazine’s website (it lives on via Google Books). Another blockbuster feature, “Power Girls,” which Mr. Roshan assigned to a young party reporter named Vanessa Grigoriadis, went off like a media-gossip I.E.D., dismembering a number of the city’s hungriest young lifestyle flacks and scattering goody bags far and wide.

Working with Mr. Roshan taught her “that writing a story is about making jokes and gossiping with your editor and then putting it all in the piece,” Ms. Grigoriadis said. “You get so spoiled writing for Maer because he cares so much, he becomes a partner. For a long time I thought that’s what all editors were like.”

Later, as editorial director of Talk, he commissioned a fashion shoot featuring Barbara and Jenna Bush look-alikes on a booze-fueled bender, leading the White House to issue a fatwa barring staffers from having any further contact with the magazine. If the boss wants buzz, you give her buzz.

One night during Memorial Day weekend, in 2002, Mr. Roshan sat in a carrel at the Astor Place Kinko’s working on a business plan. It was 4 in the morning. The place was bathed in fluorescent light. Talk had folded, and AMI C.E.O. David Pecker had reached out to Mr. Roshan to ask if he had any ideas for a new magazine. He bluffed and said he did, then grabbed a few colleagues from Talk, including Christopher Tennant and Drew Lee, and cooked up what would become Radar. The name was just a placeholder. They knew it was dumb.

He was, at that point, a media darling. “We’d watched the circulation at Talk rise by something like 19 percent in a few months,” he recalled. “If you read the press from that time, it was like, ‘It’s gotten good!’ Then 9/11 happened and they closed it. I’m like, ‘What just happened there?’”

Mr. Pecker never pulled the trigger. Mr. Roshan spoke with Jann Wenner about editing Us, but then took himself out of the running. Having a magazine of his own seemed like more fun. “In retrospect, it’s actually kind of bad-ass,” he said, draped over a chair in the crowded cafe and sipping an iced green tea. “But I was like, If I can’t find the place I want to work, I’ll just need to start something else.”

The process was draining. “I spend so much time with people at work that it becomes like a family,” he said. “So when everyone dispersed I was feeling really weird, like, ‘Where’s all my peeps?’ They went on to other things, and I went on to do this thing.”

While New York Post gossip writer Neal Travis was breathlessly reporting on Roshan sightings at the Four Seasons Grill Room (“One of the hottest media topics right now is where Maer Roshan will land next”), Mr. Roshan was mostly just waiting around for wealthy acquaintances to reply to his entreaties for funding.

“It was a lonely time,” he said. “And I remember thinking at one point: This would be a lot easier with a glass of wine. Because this is just not fun.” He let out a sigh. “That’s kind of how it started.”Full disclosure: I’m biased. I worked closely with Mr. Roshan for years under sometimes stressful circumstances. He assigned and edited two of my best stories and taught me more than any editor I’ve ever worked with—even if, O.K., he was occasionally a little bleary or zonked out on doctor-prescribed Klonopin (which as a recent article in The Fix points out, is one of the more destructive medications available).

Mostly, he was a blast to work for—mirthful, brilliant and routinely exasperating. Despite his editing prowess (he is amazing with structure and narrative), he types with two fingers and often leaves caps-lock on by mistake. He has yet to master the technical nuances of website bookmarking, and typically checks his own sites by typing in the U.R.L. He cares little for food and seems happiest with a tuna melt. “Maer has lived off pizza his entire life,” marveled Mr. Tennant, who recalled Mr. Roshan at a business lunch at Masa “holding chopsticks in his hand like a 4-year-old.”

He tends to smoke only a few drags of a Marlboro Light before firing up another, sometimes without extinguishing the first. He can be the same way with stories. I once arrived on a movie set in Williamsburg to profile a hipster porn star only to find another Radar writer who’d been sent for the same purpose. (Radar 2.0 folded before either piece ran.) During features meetings, he could often be counted on to propose pieces that seemed oddly familiar, leaving it to Mr. Tennant to remind him the story had run in an earlier generation of the magazine. That said, they were almost always a good idea, both times around.

At times, I was one Mr. Roshan’s most effective enablers. When his hands would shake, or he’d disappear for a while, I helped maintain the illusion that everything was fine, sometimes blatantly misleading colleagues about his whereabouts. Not that I invented the lies, but I dutifully repeated them: family emergencies, medical emergencies, much-needed vacations. It seemed like part of the gig.

I also cursed his name on a number of occasions, watching more or less impotently as the magazine he’d bled for went down for the final time, despite an ASME nomination for general excellence not six months before. That it later resurfaced as a shady Octomom gossip portal overseen—in an injustice that seems almost cosmic—by AMI’s David Pecker somehow made the whole thing worse, especially when they stripped the old content from the site and adopted a pink and green color scheme.

For those last few months of Radar, I was plagued by bouts of insomnia, episodes my wife took to calling “nightmaers.”

Conflicted doesn’t begin to cover it.

Then again, lots of people seem to be conflicted about Mr. Roshan. To read through Radar’s old press is to step into media steam room so cloudy with schadenfreude, you have to squint to make out the hazy figures in the corner and what exactly they’re up to. Kurt Andersen wrote a strongly worded critique of the magazine in 2005, nailing it for, among other things, its many similarities to Spy (“like a tribute band”), and published the piece in New York, the magazine where he’d hired Mr. Roshan as a senior editor a few years before.

Then there was Gawker—the outlet that had most assiduously followed the magazine’s ups and downs (branding its blanket coverage “The Greatest American Magazine Re-Relaunch”) even as the site’s own mordant take on media and celebrity arguably made the whole idea of Radar seem superfluous. Radar was a classic Gawker story. Despite having been a fan, Gawker Media founder Nick Denton remarked in a GChat, “We quite quickly made it a target. Such a lurid cast of characters.” He was referring not to the editorial staff but to the rogues’ gallery of backers, including Mr. Zuckerman and financier and sex offender Jeffrey Epstein—news of whose proclivities are thought to have led Mr. Zuckerman to dump his share of the property—and subsequently supermarket tycoon Ron Burkle and his aide-de-camp Yusef Jackson (a beer distributor and son of the Rev. Jesse Jackson, who perched on a stability ball during meetings and employed the disconcerting email sign-off “God Bless”).

“Radar was the charge of the light brigade,” Mr. Denton added. “Glorious, but not good business. It was a throwback.”

Somewhat infamously, Team Radar sought revenge during the magazine’s 2005 launch party when somebody pushed a pie into Mr. Denton’s face—a throwback sort of stunt, to be sure, but one that made for a good photo op and a Drudge pickup. Not that it quashed the beef. At one point, Gawker writer Choire Sicha posted an item suggesting Radar wasn’t paying freelancers (we were), without mentioning that he himself had freelanced for and been paid by Radar not long before. “Don’t your readers deserve to know that?” I demanded over the phone, to which he replied that it could all be sorted out in the comments. Eventually, he did append an update: “Good news! We haven’t heard from any other contributors to the new Radar who’ve had trouble! Isn’t that lovely?”

That it had by then become easier for a freelance writer to fire off an anonymous complaint to Gawker than to return an assignment contract seemed indicative of the weirdly intimate love-hate relationship a certain group of journalists had developed with Mr. Roshan. Shortly thereafter, when Mr. Sicha wound up as a Radar colleague, it seemed not only farcical but somehow par for the course. It was always complicated with Radar.Mr. Roshan’s first serious dalliance with magazines occurred in the late 70’s, and it seems to have made a powerful impression. He was a Jewish kid growing up in prerevolutionary Tehran, the son of a Persian-Jewish father and an American mother. The Roshans subscribed to Time—but their issues inevitably arrived late and incomplete.

“I don’t know how they found the time to do this,” Mr. Roshan recalled, referring to the Shah’s regime, “but they would go in and cut out everything they didn’t like, so you’d get magazines with whole articles missing.” Tidy though it sounds, Mr. Roshan’s subsequent career can be seen on some level as an ongoing campaign to shovel copy, the more provocative the better, into those mysterious blank spaces.

This did not always please Radar’s various backers, who might have wished he held certain of their sacred cows in higher regard. During my tenure, Hillary Clinton was the most sacred of all (Bill was, at the time, a frequent flyer on Mr. Burkle’s 757, “Air Ron”). I recall one dramatic showdown over a fairly tame web roundup of Hillary’s “cronies.” The story ultimately ran, but at some cost to Mr. Roshan’s relationship with our funders.

“Some would say it’s a little reckless but he does what he believes in,” noted Mr. Tennant, who pointed out that Mr. Roshan had gleefully alienated the gay mafia with “Trophy Boys” just when he was set to become a made member. “He could have been sipping Cosmos at Calvin’s beach house!” Mr. Tennant said. “And it would probably more advantageous not to put Courtney in The Fix. But to his credit, Maer is always ready to absolutely piss someone off.”

“If I’d been more willing to compromise, I probably would have gotten a lot further,” Mr. Roshan conceded.

Another formative and cinematic memory: It’s the Fourth of July at the Community School in Tehran, an academy for the children of American expats. As Maer and his schoolmates look on awestruck, a helicopter buzzes into view and hovers over the school’s courtyard, whipping up a swirl of dust. The chopper’s door slides open. The children raise their eyes to the blue sky, and McDonalds hamburgers rain down.

Meanwhile, demonstrations against the Shah were gathering steam: fevered protest marches passing right outside the school’s gates, guys beating themselves with chains, tanks rumbling in the streets, people throwing rocks and lighting piles of garbage on fire.

In 1979, Mr. Roshan’s mother whisked him and his two younger brothers back to her parents’ house on Long Island while his father stayed behind to deal with the family’s property. The Shah’s puppet government soon fell, and Ayatollah Khomeini was swept into power. Mr. Roshan’s father escaped seven years later, but the once-colorful figure was diminished. He died of cancer within a year.

After arriving on Long Island, Mr. Roshan’s mother set up a flea market booth at Aqueduct racetrack, peddling $3 belts to make ends meet. Somehow she eventually earned enough to buy a house in Five Towns and to send Maer and his brothers to an Orthodox yeshiva. Though he wasn’t religious and already knew he was gay, he seems to have fit in well. His second year, he ran for vice president of his class, and despite having to deliver his Hebrew campaign speech phonetically, he won.

Before long, he was zipping into town on weekends with a female friend to hit the nightclubs he’d read about in New York and Interview. Their first such excursion was to Area. The high-schoolers took one look at the crowd outside and quickly determined that standing at the back of the line would never do, especially if they wanted to be home for curfew. Instead, they planted themselves at a distance from the scrum in front and pretended they didn’t want to go in at all. “The bouncers were like, ‘You,’” Mr. Roshan recalled incredulously.

Inside, the theme was Religion. A guy was hanging from a cross. There was a pool of fire on the dance floor.

Mr. Roshan attended N.Y.U. as a journalism and politics major and got to know club kids Lisa E. and James St. James. Dressing for a night out was a two-and-a-half-hour process and often involved the company of a posse of drag queens. Asked to describe his look at the time, he said merely, “I wouldn’t want those pictures to surface, that’s for sure.”

After a short stint in Key West, where Mr. Roshan covered the police beat for a local paper (making sure to boldface the names in the crime blotter), he became an editor at Interview. His first article to cause a stir was a freelance piece, an exclusive Q&A he landed with Liz Smith for Outweek, despite the fact that the magazine had excoriated her for months over her refusal to come out as a lesbian. “I was being attacked constantly!” Ms. Smith recalled. “But Maer was so convincing. I honestly don’t know how he did it.” The cover story, entitled “Liz Smith: ‘I Hate Outweek!’” ran in June 1991. “I was prepared to think of him as an adversarial reporter,” Ms. Smith said. “But he was so intelligent and nice and sweet. I’ve followed his career with a great deal of proprietary interest ever since.”

The story helped win Mr. Roshan the gig as editor-in-chief of QW, his first of many start-ups. The AIDS crisis was at its height, and major staff battles over politics were routine. “There was this contingent that was, like, ‘Magic Johnson is not our hero!’”Mr. Roshan recalled.)

Mr. Roshan was part of the generation that had been educated about safe sex, he said, “which didn’t make it any less scary. But I got to see the transformation of a community,” from one that was underground and marginalized to one that was aggressively visible—a dynamic he sees happening now for addicts, and that The Fix aims to capture and accelerate.

After QW’s owner died of AIDS, Gil Rogin, the legendary managing editor of Sports Illustrated and co-founder of Vibe, hatched a plan to bring a retooled version of the magazine to Time Inc., to be called Tribe. But after Mr. Roshan presented a prototype, and then another, to the company’s board, the project was shelved, in part, it was speculated, due to fear of a boycott by the Christian right, which had recently targeted Sassy.

Mr. Roshan was subsequently hired by Mr. Andersen at New York, eventually becoming deputy editor under Caroline Miller. He became known there for an uncanny ability to nail the city’s zeitgeist, and for a playful streak. “His stories were always brilliantly full of angles,” said Ms. Brown, who was then at The New Yorker. For instance, he spearheaded a singles issue with companion-wanted ads by Star Jones, Marcus Schenkenberg, Ann Coulter and Ed Koch on the cover. (“They all got a ton of responses but Star only got three letters!” he recalled. “Poor thing.”) For a package, Gay Life Now—a first for a mainstream magazine—Mr. Roshan invited just about every prominent homosexual in town to pose together on the cover, then wrote a provocative piece wondering why so many had demurred. He initiated a column with Mayor Koch and Senator Al D’Amato kibitzing about politics at the Four Seasons, and another, “Cindy Undercover,” in which gossip writer Cindy Adams would take a job as a bartender at Scores, or a waitress at Katz’s.

“He knew absolutely everybody,” Mr. Tennant recalled. “The phone would ring every five seconds. ‘Hey, it’s Candace [Bushnell], where’s Maer?’ ‘It’s Ed Koch, where’s Maer?’ It was like, ‘Please hold. Please hold … ’”

Mr. Roshan nabbed the first postscandal interview with Monica Lewinsky, by accident. “We were at a club, and she was like, ‘You look really familiar,’ and I’m like, ‘That’s funny, you look very familiar as well!’” He also wrangled a profile of Denise Rich and noted proudly, “I think I’m the only person who was simultaneously friends with Denise, Monica and Lucianne Goldberg.”

“God bless Maer,” offered Ms. Goldberg. “He’s smart and kind, and he doesn’t stab people in the back.” They remain friends, though they steer clear of political discussions, added Ms. Goldberg, who now runs a right-wing website, Lucianne.com. “What we do is laugh about life’s situation. He’s hilarious.”

A lot of people say that about Mr. Roshan.

“He’s the most fun ever,” Ms. Grigoriadis gushed. “We would just hang out in his office, laughing all day. There’s a whole new breed of editors now who just want to email back and forth. They don’t dish. But that’s not the way to get people to tell you stuff.”

Lisa DePaulo, who wrote the Lucianne Goldberg and Denise Rich profiles, called Mr. Roshan the most enthusiastic editor she’d ever worked with. “You can’t lose your erection when you’re working with him,” she said. “The best stories in the world are the ones where you have these amazing conversations before you write. That’s Maer. You cannot not be excited. It’s impossible to punt.”

Bigger jobs soon beckoned. In 2000, Jason Binn tried to hire him to run Gotham. Mr. Roshan agreed. But after he resigned from New York, his new boss presented him with a list of “friends” who he said should be treated gently in print. There were more than 30 names on it.Mr. Roshan quickly dashed back to his old job.

Tina Brown came calling a year later, after deciding to step back from editing Talk and concentrate on the books and conferences divisions. She saw Mr. Roshan as an ideal replacement. “He just knew how to spin the news, and he could go high or low,” Ms. Brown said. “He could do hard news but he also had a great sense of humor.”

After a bit of high-level negotiation (Ms. Brown would send a limo driver over with terms, which Mr. Roshan would review, mark up and hand to the driver for the return trip), he took the job. Ms. Brown granted him the right to tinker with the magazine as he saw fit, and he engineered a redesign, changing the trim size, adding new sections and hiring a new columnist, Tina Brown.

Which isn’t to say he had total control. “Our biggest fight was she wanted to have this cover line, ‘My Aching Vagina,’” he remembered with a laugh (the story was an excerpt from Susanna Kaysen’s memoir of genital pain). “And I was like, ‘That’s not happening.’” He adopted a voice I’d heard him use before when channeling Ms. Brown, a voice that sounds absolutely nothing like her: “‘I don’t know why! It’s a very important story! I’m sure if it was called ‘My Aching Penis’ you’d have no problem with it!’”

“That sounds like Maer’s fevered imagining,” Ms. Brown said.

In the end, they went with “Susanna Kaysen’s Private Parts.”

“But those disputes were very few and far between,” Mr. Roshan went on. “I really do love her, There’s nobody more fun or funnier to work with,” he said.

To those who don’t know him, Mr. Roshan’s penchant for such dish can sound snarky. But he relates these stories with deep affection. “He just has a great eye for the tragicomedy of New York,” Mr. Tennant said. “But it’s from a good place. He has a huge heart.”

Harvey Weinstein, despite having shut down Talk not long before, was impressed enough with Mr. Roshan to join an investment group to back the original test issues of Radar. "Maer has an unbelievable weather vane for what’s going on," Mr. Weinstein said. "He had this incredible energy, and his people really loved him. He always made sure people who worked for him and with him had fun."

Mr. Roshan has always had a soft spot for “damaged-wing birds,” as Mr. Tennant put it. And in the latter days of Radar, he was well on his way to becoming one of them himself.

“You’re going to tell the steak story, aren’t you,” he declared one afternoon last month as we walked down Broadway toward Union Square.

“Probably,” I replied. “It’s kind of a funny story.”

The steak story, on reflection, isn’t all that funny. Basically, sometime in 2008, Maer and I went out to lunch at the Palm on Second Avenue. He hadn’t been himself. His skin looked yellow. He’d had a break up with his boyfriend, Matt, who’d refused to see him anymore until he got sober, and he was having bouts of paranoia, raving that Matt was secretly draining his bank account, which nobody who knew either of them believed for a second. My goal was to try to persuade Maer to quit Radar—to become a figurehead, go get well, and allow me to take over the magazine. I was looking out for him, but also for myself. It was complicated.

He promised to think about the idea. And then he looked down and declared that his steak was … moving. “No, seriously,” he insisted. “My God, look at that.”

Entering Union Square Park, we grabbed an empty bench on the west side.

“Whatever,” he said. “Just don’t make it your lede. And you might note that hallucination was a side-effect of Klonopin, which my doctor prescribed.”

“Okay, but you’re actually not my editor on this,” I taunted.

“Thank God!” he said with a hearty laugh.

Mr. Roshan was going to be late for an interview with The New York Times, but first he had something to show me. He pulled an iPad out of his satchel. He wanted to give me a taste of his latest project, a tablet magazine called Punch, after the satirical British weekly. The project’s partners include Dany Levy, the creator of DailyCandy, David Bennahum, ceo of the American Independent News Network, and designer Luke Hayman, of Pentagram, who was responsible for the last redesign of Radar.

Whether Punch would be a monthly with a daily component or a series of individual apps was up in the air. But Mr. Roshan, who has taken quite a few meetings with investors over the years, was at it again. Most of the major publishers in town had seen it and were impressed. Mr. Roshan was hopeful. Hamburgers actually fall from the sky more often than people think.

“You’re going to love this,” he said excitedly, punching at the touch-screen and loading up a feature about drunk driving Hollywood celebrities. “Pick a star,” he prompted. The options were Lindsay Lohan, Mel Gibson, Britney Spears and Charlie Sheen. I chose Lindsay, and her face appeared in the rear view mirror. He selected a car for her; then he “picked her poison.”

“Now she drives drive home through LA and tries not to hit any pedestrians,” he explained.

Punch looked awesome—by far the best iPad magazine I’d seen, and probably what Radar was always supposed to be. Still, I wondered what the recovery community would think of the game.

He took a deep breath. “That will be interesting,” he said. “But you know, I never really wanted to be a poster child for alcoholism. The Fix is a project that needed to be done, but it’s not my life’s calling. I don’t really see myself on Oprah’s couch, do you?”

Mr. Roshan cracked up. Then he added, “Is this not the fucking coolest thing ever?” and he tapped the gas.

agell@observer.com