Matthew Kenney’s restaurant career hasn’t been short on drama—accolades appearing alongside gossip-page sniping, awards followed by closures. He is, in many eyes, New York’s most profoundly enigmatic chef—a sometimes brilliant, resilient one whose story is filled with all the makings of a Hollywood movie: good looks, bad relationships, heartbreak and deceit. And lawsuits, lots of lawsuits.

Kenney arrived dramatically in 1993, when he opened Matthew’s on the Upper East Side. The next year, he was named one of Food & Wine’s “Ten Best New Chefs in America” and was nominated for Rising Star Chef from the James Beard Foundation. Then came Bar Anise, Mezze, Monzu, Canteen, Commune, Commissary and more. Along the way, Kenney built a reputation as an ingenious reinterpreter of Mediterranean, North African and Middle Eastern cuisines.

But with the celebrity-chef terrain came criticism that Kenney was undependable and egocentric—a perception that’s grown more widespread as a succession of his restaurants have closed against a backdrop of questionable financial dealings and other controversies. In the latest debacle, the vegetarian hot spot Heirloom, opened last November on the Lower East Side, has been shuttered amid acrimony and legal action.

“He was at the top of his career—and look where he is now,” says Karine Bakhoum, a publicist who took on Kenney, now 41, as a client when he was a little-known 26-year-old chef. Bakhoum was his PR mastermind for nine years and helped turn the handsome, dark-haired kitchen whiz into a name brand; she stopped working with him after a financial dispute, which was eventually settled. “He’s alienated everyone in his industry,” she adds.

If that’s true, it hasn’t slowed him down. Kenney has launched several projects since last October, focusing on his latest obsession: raw and vegan cuisine. Establishing numerous ventures under the Organic Umbrella company name, he has launched a classroom and restaurant called the Plant in Dumbo; unveiled four Blue/Green juice bars—three in the city and one in Darien, Connecticut; opened a café at Jivamukti Yoga’s new 13th Street studio; and—this just in—aligned with the owners of Crunch gyms to build another series of juice bars. But many current and former associates wonder how he continues to get such ample backing. “There are some people who are addicted to drugs, some to women, and some are addicted to restaurants,” says Boyd Willat, an inventor and Los Angeles real-estate developer who poured $4 million into Kenney’s New York eateries and earned “not a fucking nickel” back.

Kenney doesn’t dispute that claim. But the New Haven–born, Maine-raised chef says he’s hoping to leave his past troubles—and a string of frustrated investors—behind. “I’ve got a dozen businesses going on in my life,” Kenney says. “And only one of them is problematic: Heirloom.”

“I’ve got a dozen businesses going on in my life. And only one of them is problematic: Heirloom.”

Not three months before Heirloom opened, Kenney left Pure Food and Wine—a vegan raw-food restaurant that launched in June 2004 with funding from China Grill impresario Jeffrey Chodorow—in the wake of a messy split with his business partner and lover, Sarma Melngailis. The breakup of the attractive couple—who had posed together for many magazine shoots—hit the scandal sheets in July 2005, when Kenney showed up at a release party for Raw Food, Real World, the cookbook he and Melngailis cowrote, with his new 20-year-old girlfriend, Natasha Prakash, on his arm. Chodorow sided with Melngailis, and Kenney left Pure.

His real problematic period began around October 2001, when the old Matthew’s space became a second Commissary. “That takes us pretty close to when things started falling apart,” Kenney says. Within about 19 months, all of his restaurants had closed. He blames the September 11 attacks, saying his company was overextended prior to the tragedy and couldn’t remain viable in a depressed economy.

It was a period of utter chaos, according to Michael Glick, the former general manager of Commune. “He was getting liquor by buying it from liquor stores, because for over a year he was not paying the wholesalers’ bills,” Glick recalls. “Garbage was piling up because he wasn’t paying the garbage bill.” Glick

says that he, along with much of the Commune staff, went months without receiving full paychecks.

Kenney filed for personal bankruptcy in 2003. His filings show a debt to Glick of $17,000, an amount Glick maintains he has never been paid. Kenney say he’s surprised to hear that alcohol was purchased in the way Glick describes, but adds that he’s not sure which bills were paid and which weren’t, because other people wrote the checks. With so much going on, Kenney maintains, “I barely set foot in the accounting office.”

When the Commissary in New York folded in early 2003, Melngailis says she and other investors lost their money. Melngailis, 33, asserts that she’s out close to $500,000—the amount she says she put into Kenney’s ventures. “During the time I knew him,” she says, “I swung from my finances being quite positive to being quite negative.” Kenney says he doesn’t know how much she lost. “I’d like to see a breakdown,” he says. “Let’s look at the spreadsheet.”

When Kenney started making plans last fall for Heirloom, Chodorow sued, claiming Kenney was poaching staff—in violation of an earlier agreement to “preserve the assets” of Pure. Chodorow also charged that Kenney “concealed certain assets and liabilities,” that he owes “at least $1 million to the federal government as a result of his failure to pay taxes” and that he has attempted to “hide or conceal his assets.” Among the claims in his legal response, Kenney argued that he would still be involved with Pure if it weren’t for Melngailis’s frustration over his refusal to reconcile with her romantically.

Melngailis calls that charge “outrageous.” Chodorow declined to comment for this article. Kenney says Chodorow’s allegations are “preposterous.” And so it goes.

The suit hasn’t been settled yet, and there’s more: Heirloom has spawned its share of legal headaches, largely because of its owners’ contradictory strategies for increasing business. One investor, James Duffy, says the concept doesn’t attract enough customers. “A vegetarian restaurant did not work, so can we put some meat on the menu?” he asks. “I don’t see why we can’t.”

Kenney, who says he adheres to a mostly raw vegetarian diet—and starts each day with a glass of lukewarm lemon water—would have none of it. He filed suit, claiming that Duffy and the other investors, Edward Sheehan and Gerard McEntee, were ruining the value of the restaurant and that they had been “utilizing the premises as their personal clubhouse and drinking establishment.” Kenney (who was on salary) says the three investors didn’t receive money from him, but that he developed Heirloom’s concept and opened and operated the restaurant. This past Easter Sunday, according to court papers, investors informed the staff that the business would close temporarily.

Despite this latest trauma, Crunch’s COO, David Fowler, trusts that Kenney can move forward. Fowler says the chef was up-front about his past: “After 9/11, he wasn’t well capitalized. But his experience is there and his drive is there and his passion is there.”

For his part, Kenney says he attracts controversy because of the scale of his projects: “To create in this city, you’re leaving yourself open to business, and business is tough. It’s not like I’ve done little $50,000 places on side streets in the East Village, where no one’s going to pay attention. I’ve done two- and three-million-dollar projects.” Asked why drama clings to him, Kenney says he wonders the same thing. “I’m not claiming to be a victim. I don’t understand it myself,” he says. “If you figure out the answer, let me know.”