"Some big players," noted dapper Capitale owner Seth Greenberg, as he peered around the room at the competition on hand.

Smith & Wollensky founder Alan Stillman and Boathouse owner Dean Poll also attended, alongside representatives of Giuseppe Cipriani, Donald Trump and Danny Meyer's Union Square Hospitality Group, among others.

Michael Desiderio, the restaurant's current chief operating officer, was there on behalf of the late Warner LeRoy's family, which has operated the historic 25,000-square-foot eatery since 1974. The famous venue annually ranks among the top-grossing independently run restaruants in the country, earning more than $37 million in 2007. It is also a very costly and massive operation, with up to 500 employees, many of whom are unionized, which some operators view as an impediment.

The LeRoys' current license agreement with the Parks Department expires on Dec. 31, and the city is expecting big things from whomever is awarded the next 20-year contract, including substantial renovations to the building and a much larger chunk of the profits.

The LeRoys have vowed to outbid any competitor for the space. "Based on the amount of people who've walked through [the restaurant] and the amount of people who've shown up [to Thursday's meeting] I see somewhere between five to six bids," said Mr. Desiderio, who summed up the field of potential proposers thusly: "Some of it is just gawking and some of them will do their due diligence and weed out whether it makes sense as a business."

Mr. Desiderio pointed to Mr. Meyer and Mr. Stillman as particularly strong contenders. "I think these guys are all great restaurateurs and I think they're going to do their best to set forth a bid."

"I'd hate to lose a beauty contest," said Mr. Greenberg. "But we think it's worth it. … We're deep into this and I'm very excited."

Bids are due on May 1. Officials hope to award the new contract in July.

The first letter to Mr. Tierney, chairman of the Landmarks Preservation Commission, came in September from Peter Ward, president of the New York Hotel and Motel Trades Council, a union with Rainbow Room employees that has strong connections to elected officials. Then came a letter from Richard Parsons, the Time Warner chairman, who wrote there was “no more romantic space than the Rainbow Room” in New York. Then the Historic Districts Council sent a letter of approval; a similar letter from the Municipal Art Society is forthcoming; and on Tuesday night, Manhattan’s Community Board 5 was expected to take up the issue.

The sudden stream of support is no coincidence. Behind the push is the Cipriani family, led by Arrigo Cipriani and his son Giuseppe, the upscale restaurateurs who have run the famed Art Deco restaurant and banquet hall since 1999. In August, the Ciprianis—operators of four local upscale banquet halls and convicted of state tax evasion last year—petitioned the LPC to grant the Rainbow Room landmark status.

Now the family is leaning on elected officials, business executives and other big names to back its application.

The uncommon move is a not-so-subtle jab at the Rainbow Room’s landlord, Tishman Speyer, the powerful and politically connected real estate firm led by Jerry and Rob Speyer. As interior landmark designation would restrict changes or alterations to the restaurant and banquet hall, it would likely weaken the Speyers’ hand in future lease negotiations with Cipriani or any other potential tenant. It would also effectively guarantee that the Rainbow Room, or something very similar, remain the space’s use in perpetuity.

Tishman Speyer has not yet taken a position on the landmarking, though landlords typically resist such moves, as they can curb their ability to charge higher rents. Further, the Speyers and Ciprianis have been engaged in a series of spats over the Rainbow Room, as the restaurateurs have filed multiple lawsuits and the rents in the existing lease are currently being determined via arbitration.

In making the rounds for support of the landmarking, representatives of the Cipriani family have said the impetus is twofold. First, the representatives say, the Cipriani family values landmarks and wants to see the Rainbow Room’s historic look protected, like that of most of the family’s other city venues.

Second, and probably more relevant, Cipriani’s lease expires in 2013, and the family says it is worried that Tishman Speyer will try to convert the 56,000-square-foot venue to office space, which could potentially be rented at higher rates.

Kevin Finnegan, a Cipriani attorney, said that the office-space conversion was indeed a worry, but denied that financials were the major impetus behind the company’s desire to landmark the venue.

“I’d hate to have anyone get the sense that this is a primary motivation of the Ciprianis,” Mr. Finnegan said. “They pay a premium for space—they are in wonderful spaces all over the city. … They would be under constraints just like a landlord would be in terms of changes or alterations, so it’s a mixed bag in terms of the economics.”

The legitimacy of the Ciprianis’ office space-conversion fear is unclear. Tishman Speyer has denied such a move is under consideration, and preservationists and others contacted by Cipriani expressed skepticism about the concept.

WHATEVER THEIR REASON, the Ciprianis’ public stance so far makes clear that they want to position themselves to renew their lease in 2013—the firm addressed the lease expiration and potential office space-conversion issue in its application to the LPC—and to renew on favorable terms. Landmark status for the Rainbow Room, which could apply to items like furniture and lighting fixtures depending on the terms of a designation, has the potential to both decrease the market value of the space and deter potential tenants who would want to make alterations.

To realize its goal of a landmarked Rainbow Room, Cipriani has enlisted a posse of consultants and lawyers to round up the support of elected officials, executives and the community; to do its own historic research; and to craft an application to the LPC. The team consists of the lobbying firm of Capalino + Company, which is highly experienced in land use; Mary B. Dierickx, a historic preservation consultant who made the 75-page application to the LPC; and Mr. Finnegan, an attorney at Levy Ratner.

The consultants have led Rainbow Room tours and met with preservation groups including the Municipal Art Society and aides to, among others, Manhattan Borough President Scott Stringer and Council Speaker Christine Quinn, who represents the area. The goal seems to be to get the groups and officials to lean on the LPC to act on the application, a subjective decision that mostly rests in the hands of Mr. Tierney, the commission’s chairman, and his staff.

(Elected officials often pressure the LPC, sometimes with success, and Assemblyman Dick Gottfried and State Senator Liz Krueger last week wrote a letter in support of landmarking.)

A commission spokeswoman, Lisi de Bourbon, said LPC staff is looking at changes made to the Rainbow Room, and then it will make a recommendation on landmarking.

THIS IS NOT to say that many of those pledging support needed much of a push. A number of the elected officials and preservationists involved voiced strong support for landmarking the Rainbow Room, or at least the main section of it on the 65th floor of 30 Rock.

“It seems to me that the public would be upset by the loss of the Rainbow Room even if most of us don’t go out dancing,” said Peg Breen, president of the New York Landmarks Conservancy. “Certainly, the Rainbow Room, we think, is deserving of landmark status.”

It appears the biggest potential obstacle would be Tishman Speyer itself, which is the controlling owner of Rockefeller Center. It is uncommon for the LPC to landmark a property over an owner’s objections, and in this case, the owner is one of the best-known landlords in the city, with holdings that include Stuyvesant Town and the MetLife tower.

The Speyers are also one of New York’s most politically connected developers, and Rob Speyer personally raised $25,750 for Ms. Quinn last year when she was considering a run for mayor, according to campaign filings.

In a statement, Virginia Lam, a spokeswoman for Tishman Speyer, said of Rockefeller Center that “we feel our track record demonstrates that we have worked hard to respect this great and iconic landmark.”

As to the LPC’s examination: “We look forward to its findings.”

Since the Cipriani lease on the Rainbow Room started in 1999, the tenant has had a number of acrimonious quarrels with the Speyers. In 2003, Cipriani sued the landlord to remove new metal detectors that had been installed to search the Rainbow Room’s guests, claiming that the building owners sought to “maliciously damage the reputation and business of the Rainbow Room.”

The two parties have also been engaged in a lengthy dispute over the rent in a five-year lease extension, which began in February. Tishman Speyer, Cipriani claimed in court papers, wants more than $8.7 million a year for the space, compared with the $4 million base rent charged in the 1999 lease.

Seemingly connected to the lease negotiations, which are in arbitration, is a Cipriani lawsuit filed in August. The Rainbow Room managers said in a lawsuit that Tishman Speyer claimed Cipriani was in default of its lease on account of a long-faulty fire alarm system (a lawyer for Cipriani, David Rozenholc, said it has now been rectified, though each party wants the other to pay for the work).

Mr. Rozenholc says these squabbles seem to have no connection to the landmarking, though they do raise the question as to whether Tishman Speyer would be eager to sign a new lease with a seemingly intractable tenant.

As for the timetable of any landmarking, the LPC did not offer one on its decisions. With an eye on its 2013 lease expiration, Cipriani, the company said in its application to the LPC, believes “an expeditious evaluation of these important spaces is necessary.”

—With additional reporting by Chris Shott and Adam Rose

ebrown@observer.com

According to the New York Post, fellow SLA commissioners Noreen Healey and Jeanique Greene "sprung a surprise resolution to strip Boyle - the sole board member to vote against the Ciprianis - of all powers previously delegated to him to conduct authority business. Instead, the resolution required approval of the full three-member board for any actions."

Mr. Boyle, a former Syracuse cop appointed by former Republican Governor George Pataki, told the Post last week that current Democratic Governor David Paterson's administration had tried to "intimidate" him into accepting a $500,000 settlement in lieu of yanking liquor licenses at nine Cipriani eateries, including the Rainbow Room at Rockefeller Center.

Ms. Greene and Ms. Healey, both Democratic appointees, were each recently granted use of a state-owned Ford Taurus, courtesy of the Paterson administration; previously, Mr. Boyle was the only board member with state car privileges.

Mr. Boyle told the Albany Times Union "he won't be pushed out of his post, which pays $120,800 a year, until his term expires in February."

Apparently, new State Liquor Authority (S.L.A.) commissioner Jeanique Green is a big Post reader.

This morning, Ms. Green cast the deciding vote to accept a $500,000 penalty in lieu of yanking the licenses, thus allowing the Cipriani empire to stay in business.

While "it's very difficult to overlook" Cipriani's recent tax violations, Ms. Green explained that she was concerned about "the impact of our decision on the individuals who are working there."

"This is unfortunate," remarked SLA Chairman Daniel Boyle, who had streadfastedly opposed showing any leniency to the wealthy banquet behemoth.

"They can't buy their way through the system," Mr. Boyle had said earlier, adding that the liquor board was "not the Department of Labor" and "to disregard these charges is unbelievable."

Believe it. The bellinis are safe. 

After losing his valuable lease in a legal fight at the Toy Center, the dapper restaurateur now faces life without bellinis, if archnemesis Mr. Boyle has his way and puts all seven Cipriani establishments effectively out of business by stripping their liquor licenses.

How ironic, writes Mr. Stein, if "a clan that has catered to the haute monde for almost 80 years could suddenly be brought down by a normal, middle-class guy in a regular, old courtroom next month."

The article also notes how Mr. Cipriani's residential project on Wall Street hasn't exactly panned out, either:

Michael Desiderio, chief operating officer of Tavern on the Green, and Joe Cozza, vice president of sales and marketing at Cipriani USA--both of whom are facing significant challenges these days in keeping their illustrious New York institutions afloat.

Tavern, for one, faces a potential bidding war to keep its sprawling 27,000-square-feet digs at Central Park. Cipriani, meanwhile, is struggling to hold onto its liquor licenses after CEO Giuseppe Cipriani pleaded guilty to tax charges last year.

I asked the friendly Mr. Desiderio, in light of the upcoming bidding process: Was the restaurant proposing any changes to its image?

No major changes--just some improvements, he said, waxing nostalgic about Tavern's historic place in New Yorker's imaginations. "There’ll be requests for enhancing the décor and building, and additional economics, I think that’s part of it.”

I pressed the issue: Does the city want to hang on to the same old Tavern on the Green?

Mr. Desiderio said he couldn’t speak for them but that they “are committed to maintaining the work and the image of the city of New York and the Conservancy. Both the city and the restaurant are committed to running a first-class dining experience.”

Later, I caught up with Mr. Cozza of Cipriani. "It’s wonderful to show the industry what is happening to Wall Street," he said of the evening's festivities. "We are thrilled to be part of the revitalization of a community. With Cipriani’s, now it’s a residential and social space. It’s the same experience as Grand Central or Times Square. Where we used to have prostitution, we have wax museums.”

But, what about the future? How is Cipriani dealing with the possibility of losing its liquor licenses?

"We're handling business as usual and moving forward," he said, before abruptly stomping off.

This seemed to be the catering empire's mantra for the evening.

"Did you really ask that?" said a shocked Florence Mauro, also of Cipriani. "It’s a non-issue."

Dapper restaurateur Giuseppe Cipriani (ranked No. 97) had offered up $500,000 to settle his dispute with the State Liquor Authority (S.L.A.). The state agency intends to yank liquor licenses from his various posh eateries and swank banquet halls around town following his conviction last year on tax violations.

S.L.A. commissioner Noreen Healey voted to accept the settlement offer, but S.L.A. Chairman Daniel Boyle (ranked No. 21) instead chose to flex his regulatory muscle and voted to terminate all of Mr. Cipriani's licenses -- plus, impose a monetary penalty.

The split vote means that the case next goes before an administrative law judge.

When police arrived, the old terrazzo floor was cluttered with carpets, flower arrangements, candelabras, lighting equipment and tables and chairs for more than 130 guests, all leading up to a canopy in the rotunda.

Exchanging vows in the marble-walled lobby of the nearly century-old Italian Renaissance-style building, with its bronze doors and brass trim, might seem elegant and romantic.

Landlord L&L Holding Company considers it trespassing.

But the bride and the groom (court documents don’t give their names) were merely the victims and not the perpetrators that prompted the property owner’s angry call to authorities.

That swagger belonged to the Cipriani family, which runs a big banquet hall of the same name on the Toy Center’s ground floor.

Giuseppe Cipriani, the svelte, smirking, Rolls Royce-riding, 41-year-old Italian impresario who heads the family’s U.S. operations, has tangled for the past three years with L&L—and the Toy Center’s previous two landlords—over his outfit’s routine occupation of the lobby.

Late Friday afternoon, L&L decided it had had enough and served Mr. Cipriani with a notice of termination, effective Aug. 8. First thing Monday morning, Mr. Cipriani fought back with a $20 million lawsuit to block the eviction. A hearing is scheduled for Aug. 30.

THE TOY CENTER SAGA, now four separate case files thick, is just one of many legal melees in which this scion of Venetian aristocracy, heir to the legendary Harry’s Bar legacy, has entangled himself.

The most recent was his July 31 appearance at Manhattan Supreme Court, alongside his elderly father, Arrigo, for tax violations. True to form, Mr. Cipriani smiled for the cameras after copping a lenient plea with Manhattan District Attorney Robert Morgenthau. Mr. Cipriani et père were back on the streets, and back to running one of the city’s most revered restaurant empires, in no time.

Mr. Cipriani’s company, Cipriani USA, operates several high-end restaurants and banquet halls across Manhattan; it currently pays about $36,000 per month for the 22,000-square-foot private-events space inside the Toy Center. The company has insisted that it has every right to expand operations into the lobby on weekends and after 5 p.m. on weekdays. And it contends the lobby usage was never an issue until its first landlord decided to put the building up for sale.

L&L, which bought the building for nearly $500 million this past April, disputes that assertion, pointing to prior “contentious proceedings” between Mr. Cipriani and both previous owners.

The latest landlord has accused the banquet behemoth of brazenly breaking not only its lease but also city code by continuing to clutter the lobby with tables, chairs, and other free-standing structures, and also blocking off entrances during events—“despite having no permits to do so,” according to court papers.

Mr. Cipriani has blamed the permit problems on L&L, which, he argues, has refused to sign the necessary paperwork. But according to the Buildings Department, the reason for disapproval stems from “concerns about egress”—not signatures.

Meanwhile, Mr. Cipriani and company have accused L&L of waging a nasty campaign to “unreasonably, maliciously and intentionally interfere” with the catering business and to destroy the culinary outfit’s reputation as a “first-class provider of hospitality services.”

The alleged smear campaign not only has included repeated calls to the cops and to regulators, but also shoddy renovation work in the lobby that has purportedly appalled and even chased away potential customers.

On June 22, building management opened a two-foot hole in the dome of the rotunda and poked nine smaller holes in the ceiling, as part of a purported asbestos-removal program. The holes in the ceiling were covered up with panels that don’t match, and the dome was covered with an “unsightly” white plastic sheet, court papers show.

“The sponsors of the wedding last Friday were very upset at the condition of the lobby, particularly the condition of the dome,” complained Cipriani attorney Steven Wagner in a July 5 letter to L&L lawyer Jodi Kleinick.

It’s the same don’t-upset-the-happy-couple defense that Team Cipriani has employed since the lobby debacle first started three landlords ago. “It would be disastrous,” pleaded Mr. Cipriani’s former catering director, Wendy Gordon, in a 2006 affidavit, “to tell the bride and groom four days before their wedding ceremony that they can’t have their ceremony in the lobby of the building.”

And it’s not the first time that Mr. Cipriani has put his high standards of hospitality ahead of supposed safety measures. In 2003, he sued Rockefeller Center to prevent the installation of metal detectors at the entrance to the renowned Rainbow Room, which Cipriani USA also operates, citing party planners’ concerns about long lines to get through security.

According to L&L’s lawyers, the prior court record only strengthens their contention that Mr. Cipriani brazenly flouts the law.

“[I]f the City says you’re using the premises in the lobby unlawfully, what will your client do?” a judge asked Mr. Cipriani’s attorney, Mr. Wagner, according to a transcript of a January 2007 hearing.

“They’ll stop,” Mr. Wagner said—a promise that L&L claims Mr. Cipriani has not kept. (Although the city has declined to approve a permanent assembly permit for the Toy Center lobby, it has issued a temporary permit through the end of August.)

YET EVEN BREAKING THE LAW sometimes isn’t enough to stop a culinary juggernaut like Mr. Cipriani.

Consider last week’s guilty plea to a single charge of defrauding the city and state to the tune of $10 million in unpaid taxes, allegedly concealed through bogus licensing fees due to the company’s international parent, Cipriani SA, and sheltered in a secretive Luxembourg bank

In exchange, prosecutors agreed not to charge Mr. Cipriani with the far more serious crime of insurance fraud, allegedly “committed acting in concert” with former Cipriani vice president, Dennis Pappas, a reputed ex-mob associate who once managed several Cipriani locations and is now in prison.

Prosecutors came down far harder last December on the proprietors of the Park Avenue Country Club sports bar, two of whom pleaded guilty to five felonies after defrauding the city and state of the comparatively meager sum of $1.8 million.

The Park Avenue Country Club closed months ago, but Cipriani USA should easily withstand the financial hit. According to Fortune, the company raked in roughly $140 million in 2006 alone, with plans under way on a reported $300 million hotel renovation in South Beach and another $70 million hotel revamp near Beverly Hills.

Mr. Cipriani’s endurance in the highly competitive Manhattan restaurant racket may have come as a surprise, given the level of opposition over the years. He survived a legal dust-up with ever-litigious building titan Donald Trump, who, Mr. Cipriani claimed in 2005, conspired with union leaders to nix a proposed Cipriani restaurant inside Mr. Trump’s swank Park Avenue condo tower.

He survived Eliot Spitzer, who, as attorney general, accused Cipriani of gender discrimination for not hiring enough female waiters.

He even survived the seemingly never-ending picket lines of Local 6, the hotel and restaurant employees union he sued during his 1999 attempt to bar its members from working at the Rainbow Room.

At the time, some industry experts believed the labor dispute might be Mr. Cipriani’s undoing.

“I think these guys have made mistakes every step of the way,” Tim Zagat, publisher of the Zagat restaurant surveys, then told The New York Times. “With a track record like that, you wouldn’t want to bet on them for the future. And having two competing catering halls of this kind is not a harbinger of success.”

Mr. Cipriani now operates a total of five catering halls in Manhattan—and, for now, one big lobby.

- Max Abelson

"Starting at the bottom of the pile with Donald means on top of the world with the rest," said the 35-year-old native of Milan, dressed in a black Gucci suit, his shiny black hair slicked back over his ears, his Italian accent on the attack, over lunch at downtown Cipriani, where he dines twice a day. "I want to learn from Donald." Thus began Mr. Zampolli's happy transition from mogul to apprentice.

Although it's a pretty good gig for an apprentice. Mr. Zampolli will have two primary roles under one title-director of international development-in the Trump organization. In Manhattan, he'll be selling luxury condominiums at Trump Park Avenue, the newly renovated former Delmonico Hotel on 59th Street. In the past few months, he's gotten a few signed contracts, including one for a $15 million pad that has not yet closed.

Second, using his international contacts, he's expected to find wealthy buyers for exotic projects like Villa Trump, a $40 million development of private residences and golf courses in the hills outside São Paolo, Brazil. But Mr. Zampolli didn't venture into real estate to lose sleep over variances, tax codes or accommodating low-income buyers; he's after tycoon status.

"It's all about business," Mr. Zampolli emphasized. "[W]hat I want to do is work in real estate. Make it happen. Make it big!"

Mr. Zampolli is driven to the posh downtown eatery in his dark blue Maybach ("the one the rappers have"), the high-end Mercedes-Benz priced in the six figures. He is promptly escorted to the far back table, a prime seat to ogle the wealthy midday clientele. Waiters attend to his every momentary fancy-whether it's a generous helping of thinly sliced prosciutto or a plate of ripe raspberries for desert. He knocks back a second espresso in one gulp.

"I take care of the big, big money people that want to buy the expensive $9 million to $30 million penthouse that we have at Trump Park Avenue." Recently, he courted some prospective Middle Eastern buyers who sought not one but two penthouses, with hopes of combining them into what "looked like a royal palace on Park Avenue." He keeps his other car, a stretch limousine, in the garage, opting for the luxury sports car to entertain prospective buyers. "The clients are very impressed when you show them a $30 million penthouse and send them a Maybach to pick them up."

The luxury car is only one of the outward symbols of wealth that he tries to project. Mr. Zampolli's meticulously decked out in the designer suit, an embroidered custom-made dress shirt (initials "PZ" in black thread) and gold "Trump" cufflinks.

"See what he gave me," he said, extending his arm forward. More than just a favorite accoutrement, it was Mr. Zampolli's welcome-to-the-organization gift from "the Donald."

"I've known Paolo for a long time," said Mr. Trump over the phone. "He's got a great imagination. And in real estate, if you don't have an imagination, it's not going to work."

While a million would-be Trumps anxiously send out résumés for their shot on The Apprentice, it was Mr. Trump's idea for the model mogul to get into real estate, according to Mr. Zampolli. In November 2003, the idea was first broached while the jet-setting pair flew in from Palm Beach. A week later, the topic came up again at (no surprise) Cipriani, during a late dinner with Melania Knauss-the future Mrs. Trump-and superstar magician David Copperfield.

"[W]e had dinner together after the Victoria's Secret show with David Copperfield. And we talked about it over dinner, and I said, 'Yes, I want to do it.' Then, three months later, I started to get the classes, the license, the school at N.Y.U. where I took the test."

They're an odd pair-the affectionate smooth talker from Milan and the germophobic developer from Queens. And over the years, Mr. Zampolli has proven to be more than just a buddy with whom Mr. Trump can enjoy the finer things-the pricey dinners, private planes, runway shows and after-hours clubs befitting the well-rounded mogul. If not for him, there would have been no beautiful Slovenian bride for Mr. Trump.

"I brought Melania [Knauss] to the states," said Mr. Zampolli, who discovered her in 1996. Two years later, the future newlyweds first met at a fashion party at the Kit Kat Club. "One night, he met Melania at one of my parties," he said. "But, you know, it was very casual."

Casual or not, this chance encounter had great repercussions, and Mr. Zampolli later accompanied the bride and groom by private jet down to Palm Beach for the spectacular ceremony. "It was the wedding of the century. Melania looked so beautiful, so gorgeous."

"In Italy," Mr. Zampolli added, "they say that when you introduce two people that get married, you are going to go straight to heaven."

And does he believe this?

"Why not?" he said, before bursting into a hearty belly laugh.

Sure, he is more experienced with models' measurements than square footage, but Mr. Zampolli is eager to follow in his friend's footsteps-just not his schedule.

While Mr. Trump gets up at the crack of dawn to pore through The Financial Times, Mr. Zampolli is sound asleep. "I can't get up at 5 o'clock. I can get up at 8 o'clock. I'm not a 5-o'clock-in-the-morning person. I told Donald this. I say, 'We're complementary-I go out later than you, and I wake up later.'"

They may seem to be a good fit for each other, but recently, Mr. Zampolli's two worlds clashed. Besides Mr. Trump, the only other person for whom he reserves so much affection is his favorite restaurateur, Giuseppe Cipriani. "I [am] very close friend to Giuseppe. [We] always had dinner together," he said between bites of seared tuna tartare, safely snug within his cream-colored sanctuary on West Broadway. "I feel at home here." And now, the real-estate apprentice is caught in the middle of a legal battle between these two friends-the one who signs his paychecks and the one who fills his stomach.

On March 23rd, Mr. Cipriani sued Mr. Trump for $5 million over a deal that fell apart at Trump Park Avenue. According to the complaint, Mr. Cipriani signed a contract to buy a ground-floor space in the luxury condominium building with the intention of opening a new restaurant. The main disagreement involved obtaining proper union approval for the restaurant. Each side now blames the other for the mess. Not only will there be no Cipriani restaurant, but the two sides are battling over a deposit paid and never returned.

"Funds were advanced in good faith, and we believe our client is entitled to the return of those funds," said John D'Ercole, a lawyer representing Mr. Cipriani.

Not surprisingly, Mr. Trump sees the situation differently, and has no intention of giving back the money that Mr. Cipriani put in escrow.

"It's very simple. I made a deal subject to Cipriani being able to get union approval, subject to various things. Cipriani was unable to fulfill his obligations under the contract, and we terminated Cipriani," said Mr. Trump.

Although Mr. Trump admitted that the powerful pair might one day be friends again, he has no intention of paying back the money.

"Look, I like him a lot. But he was unable to fulfill his obligations under our deal, and he lost his $1 million deposit," he said. "He sues a lot of people. He doesn't win, but he sues a lot of people."

Mr. Zampolli has tried to stay neutral.

"Well, they had some contract disagreements," he said over the phone after the court papers were filed. "Even though they are friends, both of them are of very strong-minded."

Changing His Image

And Mr. Zampolli, who's notorious to the city's gossip columnists for his incessant self-marketing, has got a bigger challenge on his hands: how to turn around the reputation that he himself has created. He contradicts the media perception that he's had countless girlfriends ("I'm at No. 8"), and that he desires boldface-name status for partying ("I don't do anything that should make me go in Page Six"). He eagerly discusses his family life, e-mailing his mother daily in Milan, and says that if he has children, he never wants to "tell them I'm a model agent."

A former competitor who's seen him grow in business for over 15 years believes that Mr. Zampolli can be successful, but should be more mindful of his image.

"I've known Paolo from before the beginning," said John Casablancas, founder of Elite Model Management.

"I think he's going to have to project a more serious image about himself," said Mr. Casablancas. "He likes to make fun of himself. He likes when people don't take him seriously, and that's all right. He just has to mature his image a little more."

That lighter side just may be one of Mr. Zampolli's advantages. His flair for catering to the whims of high-end buyers seems to have appealed to his new boss, who regularly favors street smarts over freshly minted Harvard M.B.A.'s when judging new recruits on The Apprentice. But will his experience wining and dining clients in the fashion world be enough to convince the world's wealthiest to move into a Trump villa or penthouse? That remains to be seen.

"If you have connections, it is very helpful, especially if you are going to work for a celebrity type like Donald Trump," said Jacky Teplitzky, executive vice president, Prudential Douglas Elliman. However, she recommends caution. "People coming into the real-estate profession should get educated about all segments of the market."

While he can never be criticized for having low self-esteem, even Mr. Zampolli is well aware that the career change may be a bumpy ride.

"[T]o get a girl from the middle of Brazil that doesn't speak English [and] put her on the cover of Vogue is very different than building skyscrapers in Manhattan."