Ciao, Paolo! Donald’s Matchmaker Goes From Pin-Ups to Penthouses

Paolo Zampolli, a boldface name familiar to any casual reader of Page Six, did some soul-searching last fall. The founder of ID Models, who’s better known for enjoying bottle service at Lotus than for his business acumen, had just lost a public auction to buy Elite Model Management last August, and he was starting to realize that he needed to make a change. In the months that followed, he looked at his life and plotted his next move. In early December, he called an old friend about a business proposal made to him over dinner a year earlier. While on the phone in his Varick Street office, Mr. Zampolli finally heard the magic words from Donald Trump: “You’re hired!”

“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.”