The thing is, have you ever actually tried to buy Playboy? I haven’t, at least not since I was about 12. It’s real embarrassing. First I tried grabbing it off one of those corner newsstands, but seemingly every time I started to ask for it, a colleague would walk by. Fine. I tried a magazine store. Which, again, should be a fairly easy operation–so long as you don’t mind looking like a lech. I did manage to eventually escape with a copy, brought it back to my office and tried to furtively read my friend’s piece without it appearing that I was ogling Nikki Ziering.

Therein lies the challenge for former Maxim editor James Kaminsky, Playboy’s new editorial director. The August issue, on stands now, is the first where Kaminsky has the mag’s top editorial spot to himself (besides Hef, of course); he had been sharing the post with Arthur Kretchmer, the man at the top of Playboy’s masthead since the late 1960s. Playboy is still the best-selling men’s magazine–with a circulation of more than 3 million, it more than quadruples titles like GQ and Esquire–but it’s being squeezed from both sides, with almost-nude (and arguably sexier) spreads appearing in the laddie magazines and hard-core, um, co-ed spreads appearing everywhere else. (Those hard-core spreads ain’t doing so well, either. Amazingly, Penthouse hasn’t had a new issue on stands since late April, according to a spokeswoman, although she said a new issue would be on sale later this month. For a supposedly monthly magazine to go more than two months without a new issue–and without anyone in the media firmament even really noticing–is as good a sign that Bob Guccione’s empire is on its last legs as any.) It used to be that men angling to look at sultry women had to turn to nudie titles, and the compulsion to see skin overwhelmed any embarrassment. But now, there are plenty of titles that show women almost naked, everything from Rolling Stone to Maxim to Entertainment Weekly.

Playboy’s not the only once-iconic magazine that’s struggling to get a toehold in today’s increasingly fractured media landscape. In a weird way, the country’s supermarket tabloids (The National Enquirer, The Star, The Globe, etc.) are facing the same challenge. The Enquirer used to brag that it was the best-read weekly newspaper in the country (whatever that means). Now, it’s entering its second decade of declining circulation; plenty of other outlets, including a whole host of glossy magazines, provide essentially the same content, just printed on nicer paper. There’s still a sizable audience for the supermarket tabs, but there’s a much bigger group of people who are actually interested in dishy gossip and tawdry tales but are sheepish about reading The Star on the subway.

Which brings us to Bonnie Fuller. Fuller jumped ship at US Weekly last week and fled to American Media, owner of virtually all of the tabloids in the country. During her 16-month tenure at US, Bonnie forced out virtually the entire editorial staff of the magazine–the only holdover is reality-TV maestro Ben Pappas, who has so internalized the lessons of “Survivor” he actually outlasted Bonnie on the island of Jann. But even in her short tenure, Bonnie did manage to make Us a hot title, at once trashier and more successful. It was referenced on “SNL,” held-up during morning news shows and made fun of on late-night TV.

Now she’s charged with doing the same thing with American Media’s titles. It’s a tall order. Steve Coz, the man who had been in charge of the tabs, has slowly been pushing them toward respectability for more than a decade–as far back as the O. J. trial, the Enquirer was getting props in The New York Times for its scoops. But the supermarket tabs have been losing circulation for over a decade; it’s hard to build an audience when you’re producing a product people are embarrassed to be seen reading on a plane.

The stakes are pretty high. Sure there’s her reported $3 million a year in salary and incentives, but it’s unclear what new ships Bonnie can jump to if she fails here. Her skill at moving magazines off of newsstands is second only to her incredibly poor political acumen; Bonnie hasn’t only left a string of magazines in her wake (US, Glamour, Cosmo, Marie Claire and YM) but a string of infuriated bosses and underlings. At US, Bonnie didn’t just get another job, she coyly delayed signing a new, three-year contract (reportedly over a couple grand in circulation bonuses) until she could land a better offer. At Conde Nast’s Glamour, she alienated the empire’s other editors and publicly sniffed around for other jobs until her bosses got sick of it and just sacked her. If Bonnie’s not able to remake The Star into next year’s hot title and the equally mercurial David Pecker finds some way to get out of her contract, where else could she go?

Unless Playboy’s numbers are still dropping a year from now.