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After just six months as digital editor, Jellinek was at a friend’s bachelor party in Squaw Valley when Jerome Kern, then the interim CEO of Playboy Enterprises, called and said, “Hef wants to see you.” Kern told him the company was consolidating its print and digital operations and was moving the magazine’s editorial offices back to Chicago, and he offered Jellinek the editorial director’s job. Chris Napolitano, a 20-year Playboy veteran who then occupied the top chair, wanted to stay in New York. (He remains the magazine’s editor-at-large.)
“I think I was already eight beers in at that point,” recalls Jellinek, and the drunken racket of his friends was drowning out the conversation. “It was surreal. I’m on a cordless phone outside going, ‘You guys, shut the fuck up!’”
The next morning, Jellinek flew to Los Angeles to meet with Hefner for the first time. “It isn’t a done deal till you look the man in the eye and he thinks you have what it takes,” he says. Hefner was impressed.
Jellinek’s leapfrog jump to editorial director came as a shock to most Playboy staffers. “I think a lot of people at first were like, ‘This guy?’” recalls Baime. Among other things, Playboy had already bought into the lad-mag vibe before, via James Kaminsky, with mixed results at best. Would Jellinek simply be Kaminsky 2.0?
But soon after taking the job, Jellinek read 30 years’ worth of the magazine, front-to-back, to get a fuller understanding of Playboy’s look, feel, and voice during its prime. He also exercised good retail political skills—ingratiating himself with his colleagues over drinks and conveying his approachability. He likes to say that he welcomes and encourages input and ideas from anyone, even from the lowest rungs of the company. In a taped interview for Crain’s “40 Under 40,” for instance, he states: “I’ve found that by letting ideas bubble up from the bottom, come from anywhere—I don’t care if you’re the receptionist or work in the mailroom—if you’ve got a good idea, it’s going to go in the magazine, or it’s going to go on the website.”
Sounds good, but when I ask one Playboy staffer about that assertion, he snickers and says, “I’ve never seen an idea from the bottom, ever, anywhere, and I’m talking across the company.”
Minor griping aside, Jellinek has won over most of the close-knit staff. “People who are thrust into positions of power so quickly, like he was, tend to be disliked, whereas Jimmy’s not,” says Baime. “Let me put it this way: We have lots of fun. Lots of it.”
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On my second visit with Jellinek, I sit in on one of Playboy’s weekly editorial meetings. It’s the first week of January, and some 20 editors and assistant editors are gathered in a conference room to go over the March and April issues. Looking tanned from a recent family vacation in Mexico, Jellinek sits at the head of the table and runs through the monthly lineup: Is the cologne story turned in? Is there good art for the feature opener? As he ticks through the long to-do list, one can almost see Jellinek’s tan begin to fade. “There’s a lot of shit hanging out still,” he tells the group, as if to say, “Let’s tie up the loose ends, pronto.”
Though Jellinek’s place is at the head chair, Hugh Hefner looms in the room like an elephant wearing silk pajamas. “Has Hef seen it?” “Will Hef like it?” Jellinek regularly asks the others. At one point he warns the group that “Hef is in, like, typo mode”—meaning read your copy carefully, so as not to annoy the boss.
Afterward, I ask Jellinek if he ever feels hamstrung by Hefner’s penchant for micro-managing. “Hef is the editor in chief of the magazine 8,000 percent,” he says. “Like, everything I do, I do for him. I want to hit a home run for him every single time.”
What if you disagree with him?
“You don’t argue with Hef,” Jellinek says. “He’s the editor in chief, man, so his say is final.”
Separately, I raise the question of what Playboy staffers call the “Hef factor” with Mr. Playboy himself. “I suppose, quite frankly, that it’s a team operation,” Hefner tells me by phone from the L.A. mansion. The magazine, he continues, “has always been a very personal book for me. I’m not looking for someone to reinvent the wheel. What I’m looking for—and what I got from Jimmy—is a fresh take on classic Playboy.” In other words, don’t count on Hefner, who turns 84 in April, to step aside anytime soon.
Arthur Kretchmer, among others, acknowledges that Hefner can be stuck in his ways but says Hef has been loosening his grip gradually over the years: “There’s a lot of ingrained habits there. Hef will give Jimmy the freedom as they go along, as he believes in him.”
In the meantime, Jellinek has not been shy about messing with convention or sweeping away some of the magazine’s cobwebs. Marge Simpson, for example, was the first cartoon character ever to make Playboy’s cover. He all but scrapped the NFL preview coverage—shrinking it to less than a page—in favor of an oral history of the badass Oakland Raiders teams of the 1970s. He has also pushed for edgier interviews, such as the one with Seth MacFarlane, the creator of Family Guy, as well as for more graphic novelizations, including one based on Quentin Tarantino’s Inglourious Basterds.
Hefner and the corporate brass have so far liked what they have seen. “The magazine once again can say very legitimately, ‘You read it for the articles,’” says Hefner, laughing.
Last November, Scott Flanders, the CEO, promoted Jellinek to oversee all of Playboy’s ancillary entertainment businesses. In this role, Jellinek has a hand in developing shows for Playboy TV and its satellite radio station. For example, Jellinek helped drive a recent decision, along the Tiger Woods line, to nix a proposed TV reality show in which homely women from small-town America would receive Playboy-style makeovers to become Playmate material. Flanders recalls, “Jimmy immediately said, ‘Nope, we’re not doing that. Playboy is about beauty. We’re not going to associate Playboy with women that don’t meet our standards.’ Had he not been at that meeting, the result would’ve gone in a very different direction, because an idea like that—like the ‘Girls of Tiger’ idea—immediately sounds interesting.”
Some wonder, though, if Jellinek can juggle the magazine duties with his other tasks. “Editorial director is a debilitating job by itself—you have to put up with a lot of stress,” says Lee Froehlich, Playboy’s executive editor. “How’s this guy going to do two jobs? I keep thinking, like, he’s going to start crumbling under the pressure, but so far he’s been able to avoid it.”
“I like to be challenged,” Jellinek says. “If I’m going to fail, I’d rather fail spectacularly than succeed meekly.” Then, paraphrasing a line from Top Gun, he adds, “I’m not happy unless I’m going Mach four with my hair on fire.”