When you've had all that fun with Donald Trump, what do you do now that The Donald has run out of cash and cachet? When New York's Downtown scene has lost its glitter, and no one cares for old jokes about table-hopping with Jay McInerney? When "Separated at Birth" is so widely copied that everyone forgets who invented it? When your magazine is struggling to stay on its nimble feet amid big shifts in the politico-economic winds?

Born in late 1986 when Wall Street was still soaring, Spy rose by satirizing New York's big-money movers and shakers, publicity hounds, and various self-promoters. When many of those same people fell to earth three or four years later, Spy's fortunes plummeted as well. After shooting up to 150,000 virtually by word of mouth, circulation grew stagnant. Ad pages plunged from an average of fifty or more an issue to about twenty this spring. Staff members were laid off, the publishing schedule was cut back from twelve issues to ten, and for a time the magazine seemed in danger of going under.

What went wrong? One obvious factor is the recession, which has been particularly brutal to small, independent, thinly capitalized publications. Another is the strain of trying to remain hip and funny month in and month out. A third might be called the zeitgeist factor, the fact that times change, attitudes shift, and what's caustically amusing one year may be merely caustic the next. "When the perception is that you're very, very cutting edge and smart and a step ahead everyone wants to read you and talk about you ad advertisers want to be in your pages," says disgruntled ex-Spy investor and publisher director Steven Schragis. "When perceptions turn around, you become something to stay away from."

Spy's finances have stabilized since last year's dizzying plunge. After spurning an offer from Conde Nast owner S. I. Newhouse in 1988, Spy sold out two years later for around $ 5 million to a group of investors that includes advertising mogul Charles Saatchi. Although the magazine is still losing money, the capital infusion gives it more time to try to get hot again.

For a time, the perception of Spy was that it was very hot indeed. Media mavens devoured its insider gossip about The New York Times, the television networks, and Hollywood. Spy's highly mannered use of nasty appositives ("short-fingered vulgarian" Donald Trump, Abe "I'm Writing as Bad as I can" Rosenthal, and so on) became a widely copied trademark.

It was its savage profiles, however, often filled with amazing inside dirt, that caused people to sit up and take notice -- for better or worse. One article portrayed the publisher of an upscale giveaway magazine on Manhattan's Upper East Side as a raving, obscenity-spewing "harridan" who is ashamed of her working-class Jewish roots. She even gets trashed in the article by her own mother for being a social-climber and a snob. Another piece detailed what it said was the bizarre, scatalogical humor of a certain fashion publisher. A third tracked the evolution of self-obsessed columnist Bob Greene's hairpiece from the bushy early seventies to the tidied-up mid-eighties.

All of which had people buzzing for a while, until a certain reaction ensued. "Did you know," asked a front-page story in the March 8, 1990, Wall Street Journal, "that a well-known executive . . . actually 'ordered a female employee to carry a wine bottle filled with his urine' to someone at a party. . . ? Do you care? It's in Spy."

"This was a story that was very honest about a guy who is very problematic and difficult," counters Spy co-founder Kurt Andersen. "All these are vigorously reported, factually unchallenged profiles of people whose behavior and beliefs are obnoxious. What are they saying? That we were mean for portraying [Avenue publisher] Judy Price's meanness? I just don't get it."

The thirty-six-year-old Andersen, who also writes about architecture for Time and contributes occasional essays to Rolling Stone, is known among some ex-staff members as the polite, well-educated half of Spy's top duo. Strolling through Spy's loft-like downtown offices (lots of brick, heavy wooden beams, and exposed aluminum ducts), wearing a pinstriped shirt and red paisley tie he is the picture of the member of the upper-crust Century Association that he, in fact, is. Co-editor E. Graydon Carter, on the other hand, is less polished, despite his severe Anglophilia (he wears hand-tailored Saville Row suits and writes a weekly column for the London Evening Standard). A 1989 investigation by New York magazine (a frequent Spy target) found that the Canadian-born Carter had embellished his resume by saying he had graduated from college (he had not) and had written speeches for Pierre Trudeau (Trudeau's speechwriter had never heard of him).

Admirers portray Carter as an enthusiastic cheerleader for his overworked, underpaid staff, someone who dresses up as Santa at Christmas parties and has a rip-roaring time bouncing employees on his knee. Critics see the forty-one-year-old editor as enthusiastically adolescent. Carter himself admits getting carried away and spitting drinks at staff members during a raucous monthly "closing" party. "He's highly conscious of being one of the oldest people on the editorial side, so he thinks he has to act in a juvenile way," a Spy veteran says. "Or maybe he's just juvenile."

Having helped define one decade, can Carter and Andersen adjust to a new one? Jokes about the lean and hungry nineties have already been creeping into Spy's pages -- including one in the March issue about jobless college graduates "forced to live with their parents and work in tolerably 'brainy' minimum-wage jobs: clerk in bookstore, . . . waiter in cafe that serves Celestial Seasonings teas, intern at satirical monthly magazine." The May issue includes a profile of Los Angeles Uber-cop" Daryl Gates that, despite the obligatory style-obsessed put-down of "his blue doublevent suit, powder-blue shirt, and matching powder-blue pocket square, blue foulard tie and very shiny black shoes," was surprisingly untrivial.

"1990 was kind of a boring year," says E. Graydon Carter, "but 1991 is shaping up to be more exciting. You've got a city on the verge of collapse, the Palm Beach story, the Kelley book, and a war. This is a lot of stuff crammed into five months of what was supposed to be a very boring decade."

Yes, but will it be a decade for Spy? Some have their doubts. "Spy and Trump were locked in a weird pas de deux," says journalism professor Abe Peck of Northwestern University's Medill School of Journalism, "and I think they both waltzed off the poop deck together."

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