The hotel room was boring.

So Alex Goldberg did what he normally does when he’s bored, which is often: He sneaked out. It was last year, and he was vacationing with his mom and sister at the Ritz-Carlton in Miami. But Alex wanted to go where the action was. He shuffled out of the lobby of the Ritz and cruised down Collins Avenue along the row of Art Deco hotels. There was a party going on at the Delano. Alex marched through the crowd in cargo shorts, belly out in a baggy T-shirt, sneaker laces dragging. He found a spot on the edge of the pool and plunged his toes into the water.

“What are you doing here?” asked a woman in a bathing suit. “Where are your parents?”

“Taking a nap at the Ritz. I just wanted to check this place out.” She didn’t believe him. “C’mon. I know you. I did a casting with you in New York.” Alex shook his head. “No, you didn’t.”

“I did too. Your name is Josh something. You’re 11. What’s the name of the movie you were in?”

“I’m not in any movie. And I’m 12.”

Alex borrowed a video camera from the woman’s friend and disappeared into the crowd to interview people. He found his first victim in the shallow end. She was a blonde in a blue bikini, clumsily moving to the music.

“Are you a professional dancer?” Alex asked sarcastically.

She looked curiously at the four-foot-nine-inch-tall boy. “Are you making a movie for school or something?” she asked. “Is this … educational?”

Alex was grinning. Her friends started getting ideas. “Show him some ass, girl,” said one. Shake it a little. And she did. She turned around. Jiggle jiggle jiggle.

Next up: Jamie Foxx. The actor was near the bar, giving a woman a massage, and saw the crowd now gathered around Alex. Foxx offered to buy him a drink. What do you want, little boy? “A piña colada,” Alex said. The crowd laughed, and he got one, virgin.

Alex’s adventure ended hours later, at Nobu, where the pool crowd had migrated to feast on junket sushi. He had been chatting up Venus and Serena Williams at a nearby table, and mugging for cameras with a cigar hanging from his lips while eating a bowl of ice cream. Then the faces at his table went blank. Alex looked up and saw what they saw. His mother.

Busted.

If you catch him leaving school or going to basketball practice, Alex can seem like any other New York kid. He has long shaggy hair and big round cheeks, and looks young for his age (he turned 14 last month). He’s student-council president at his private school on the East Side. According to his Facebook profile, he likes “Golf, Tennis, Baseball, basketball, Soccer, Knicks, Waterskiing” and musicians like Akon, “Weird Al” Yankovic, and Black Sabbath. He likes to skateboard. He likes cool clothes. He talks a lot on his cell phone. He worries about girls he likes and whether they like him back.

But Alex isn’t like other boys his age. He’s had free rein over the streets of Nolita since before he can remember, and he quickly learned the rules of that playground, turning his relationships with the neighborhood’s shop owners into access to free gourmet meals and designer clothes and trendy sneakers, then turning those freebies into even better stuff (like courtside Knicks tickets), and leveraging those perks into even more valuable things, like connections to athletes, rappers, nightclub owners, and so on. On any given day after school, you can find him strutting down Elizabeth or Mulberry or Mott, past the foundations of his barter operation. He’s worked at Supreme, the clothing store and skate shop on Lafayette. He’s helped the chefs at Peasant. On Sunday mornings, he likes to get to DiPalo’s early, before the noon rush, and stretch the mozzarella with Louie, the cheese store’s owner, and kibitz with Violanda, his 80-year-old mother. He helps out at Papabubble, a designer candy store that opened recently on Broome Street, and hawks peanuts at Vinny’s Nut House on Mulberry and Grand. “He’s like a man trapped in a baby’s body—that’s how I always describe him,” says Vinny Peanuts.

After school for the last couple of years, Alex clocked in at his favorite job of all: at NikeID, the design-your-own-shoe mecca. He scored this gig by accident. He was hanging out on the sidewalk in Nolita, smoking a cigarette in big dramatic puffs, when a striking woman in her twenties passed by.

“You know,” said Vashtie Kola, “you smoking a cigarette is not cool.”

“It’s a fake,” he said. “Don’t worry, my babysitter is right over there.”

Alex was 9 then. Kola didn’t believe him. She noticed Alex was clutching a green bottle.

“Is that a Heineken?”

“No. It’s a Pellegrino, duh.”

Then she laughed, and Alex was in with her. “What comes out of his mouth just doesn’t match what he looks like,” she says. “It’s as if he’s been living on his own for years.” He took her to the store where he bought the gag cigarette, and she bought one, too. They strolled up Elizabeth puffing on their fake butts.

Kola worked at NikeID at the time, and she introduced him to the sneakerheads there. They can be an exclusive bunch, but Alex talked his way in. “He’s a hustler,” says Kola. “A natural-born hustler.” Before long, he was a part of the crew.

As in most of his jobs, he didn’t work for cash—child-labor laws wouldn’t allow it. He worked for the connection, which was worth far more. With steady access to NikeID, Alex turned himself into a valuable commodity, especially with the Knicks. He started supplying players and officials in the front office with shoes—a gift for sneaking him into games.

He now sits courtside, and eats dinner in the green room with the players’ families and friends. “It’s like he assumes that he’s supposed to be here, and so everyone else thinks he’s supposed to be here, too, and it’s like now he really is here,” says Adia Revell, a former college player who knows him from the Garden. Alex’s favorite Knick is center Eddy Curry. “This is my little guy right here, my second assistant,” Curry said about Alex at a recent game. “He tells me about my rebounding and positioning. He’s the funniest kid I ever met.” Nate Robinson, the team’s dunk specialist, is also a fan. He likes Alex’s shoes. “I saw the sneakers he was wearing and said, ‘Now, those are some sneakers I would want to see on my feet.’ ”

For networking purposes, Alex always carries his own business cards. He had 500 printed last year. “ALEX GOLDBERG,” it reads. “CALL FOR KICKS, TICKETS AND CLOTHES.”

The Goldbergs live on the top floor of a rent-stabilized building on Broome Street. The loft is airy and neat, with tall ceilings and skylights. Alex’s father, Richard, gut-renovated the place himself when he first moved in, in the early seventies. He now works as a wine consultant and has just uncorked a bottle of Côte du Rhône. He pours a glass for Alex’s mother, Robin, dressed in skinny jeans and a designer blouse, as they sit down to talk about their son.

Alex is “a phenomenon,” says Robin. “A self-made man.” She’s constantly surprised by how many people he knows. In California, a man recognized Alex from the salad line at Peasant. In the Hamptons, people ask, “Is that cool little kid your son?” Her trainer at the gym knows Alex; he bought shoes from him at NikeID. Occasionally, she even thinks about asking his help to get into places. “It’s cool,” she says. “He’s master of a universe that he’s created for himself.”

Richard credits Nolita for Alex’s development. “Look around,” he says. “Look at what and who Alex has at his disposal.” This is why Robin has worked to help keep the corporate intruders out of their neighborhood, at least as much as possible. Peasant will show him how to cook a goose; Starbucks won’t. “It’s hard to imagine Alex growing up the way he has anywhere else,” she says.

Robin worries, of course. She worries about “maintaining his childhood.” She worries that he’ll develop an inflated ego. And she worries that all the attention he receives for playing grown-up could lead to problems with other kids. While Alex does have friends his own age, like Julian Schnabel’s twin boys, Cy and Olmo, he can be a bit of a schoolyard bully. And earlier this year, Alex was temporarily suspended from school for calling his teacher a “dick” under his breath. His teacher needn’t have taken the comment personally. Alex curses at everyone, even his parents. “Like, he’ll be in the middle of the restaurant and say, ‘Fuck you, Dad.’ I mean, it’s crazy,” says Frank DeCarlo, the Peasant owner.

Richard and Robin try to discipline Alex about his language, but overall they’re lenient. In Miami, instead of grounding him for sneaking out, Robin let him hang out with the Delano crew all weekend. (At one point, Alex found himself chatting up three topless women on the beach. “He was literally surrounded by six grade-A Miami titties,” says Fernando Gil, a former “Page Six” reporter who met him there. “He was like a kid in a candy shop.”)

The Goldbergs don’t consider themselves a traditional family, and they’re proud of Alex’s precociousness and ingenuity. Richard is impressed when he goes to Knicks games with Alex and watches his son chat up Jay-Z and Beyoncé. He feels the same way when Alex calls from the golf course near his camp in Maine, asking him to send Cuban cigars by FedEx so he might bribe his counselors. Richard was never like that as a kid. He never had that uninhibited ability to create these kinds of opportunities. “All you really have to do is let him loose,” he says.

This is about when Alex shuffles in. “C’mon,” he says. “Let’s go to my room.”

Alex’s room is an adolescent Shangri-la: Xbox, flat-screen TV, PlayStation, digital cable, a loft bed, guitar, bass, amp, goldfish, his own artwork, flags, Knicks ticket stubs, and his treasure: at least 60 pairs of Nike sneakers. He sits in a butterfly chair, one leg slung over the edge, the untied laces of his shoes dangling loose like jungle vines. His hair hangs so low over his eyes it’s hard for him to see, so he fires off short pfffs of air, up and fast, to get it out of the way. What, I ask, does he want to do when he gets older?

“I want to own Nike,” he says.

Almost as soon as he’s said it, he’s bored again. “Let’s get out of here,” he says with a pfff. “I want a coffee.”

It’s almost ten. He needs to get to bed. Robin says no. Alex doesn’t do no. Robin raises her voice.

“Alex!”

“Robin!”

She folds. Alex is already at the elevator.

The street is the one place where Alex does not get bored. He darts between the old Italian-meat-market crowd and the Chinese vendors hawking pashminas and the tourists puttering around what’s left of Little Italy. How, I ask Alex, has his neighborhood changed?

“I don’t know,” he says, cutting across the street. “I don’t remember anything.”

He keeps on moving, calling out to strangers we pass, never stopping for a response. “Hey, what’s my fortune?” he asks a gypsy. “Hey, can I sit on your bike?” he asks a Hells Angels type. When we make it to his coffee spot, Ferrara, on Grand, he orders a decaf cappuccino. “They make the best coffee here,” he says. “The best.”

Alex is something of a gourmand. “That’s a good olive right there,” he’ll say. Or: “That’s a good burger right there.” Or, as he dunked a hunk of bread into the garlicky wine broth pooled at the bottom of a bowl of linguine alle vongole one afternoon: “That’s the shit right there!” The greatest insult is when, at a restaurant where he is not known, the maître d’ reaches for the kids’ menu.

“He’s really advanced, as far as food goes,” says DeCarlo. In the Peasant kitchen, Alex is always asking questions. Like: “Where you’d get that guinea fowl?” Or: “Those are nice razor clams, I saw them on the beach last week.” And: “Oh, you’re using pig’s liver; I had calf’s liver last night.”

He’s not a bad cook, either. Violanda, at DiPalo’s, remembers one morning when she was making an omelette with asparagus and Romano cheese.

“Why don’t you use Parmesan?” Alex asked.

Violanda explained that she had learned the recipe from her mother, and that Romano is the cheese of Sicily, the region where they lived. Parmesan is from the North.

But Alex thought the dish could be improved upon. “Parmesan is a little more delicate,” he told her. “It wouldn’t take away from the asparagus.”

Then he got an idea. “Viola, I’m going to make you breakfast this morning,” he said. He came back an hour later with an asparagus omelette, just like she’d made, only with Parmesan cheese. “I’m telling you, that dish looked gorgeous,” says Violanda, who now uses Parmesan in her omelettes. “I said, ‘I can’t believe, Alex, you can do such a thing like this!’ So beautiful. And he was so proud to do it for me. I kissed him and said, ‘You are something unbelievable.’”

Over our cappuccinos, I ask Alex what he thinks the difference is between himself and his friends. He takes a steamy sip, leaving a foamy cappuccino mustache behind. “I’m more mature,” he says. “Isn’t this coffee the best?” Then he’s out the door and heading up the street to a Chinese shop. He pops out a few minutes later, wearing a pair of white sunglasses. Wait, how did he get those sunglasses? He doesn’t have his wallet with him. When I ask about them, Alex knows what I’m getting at. He walks back to the elderly shopkeeper, waits until she’s not looking, and drops the shades on the ground behind her. Then he taps the woman on the back. “Excuse me, ma’am, I think you dropped these.” The lady turns around and takes the sunglasses. Alex is grinning. “What a good boy,” she says.

Alex doesn’t always get away with things. In fact, he’s annoyed a few of the adults in his life with his antics. At the San Gennaro Festival, Vinny Peanuts got mad at him for squeezing customers for tips while selling torrone. In only a few hours, Alex had amassed more than $150 in gratuities, all in singles.

“Alex,” Vinny said. “You can’t keep asking the customers for tips. It makes them feel uncomfortable.”

“You’re just jealous,” Alex snapped back.

Vinny threatened to send him home, but Alex called his bluff. “Send me home then. You make more with me here, and you know it.”

“Some kid,” was all Vinny could say.

Alex also ran into problems at the NikeID store, especially when his juvenile sense of humor highlighted the yawning age difference between him and everyone else in the store. One day, a client with a large nose came in to design his own sneakers. As everyone sat around the computer, Alex typed in a suggestion for words that could appear on the side of the shoe: big nose. Alex cracked up. His colleagues didn’t.

Occasionally, he was sent home from NikeID. The primary force behind these banishments was “Super” D.J. Clark Kent, the hip-hop producer who famously discovered Jay-Z and can often be found hanging around the store. “All of this can’t possibly be good,” says Kent about Alex working there. “The reason Alex is bored is because people let him do whatever he wants. Someone has to be the grown-up around here and tell this kid to go home and do his homework.” One afternoon in Soho, Alex spotted Kent on the street and left his friends to rush right over. He wanted to hang. Kent didn’t. “I said to him, ‘Alex, we’re not friends. We cool. But we’re not friends. You’re 13. I’m 40.’ He’s just completely out of his mind. He thinks we’re the same age.”

Alex never told his parents about getting sent home from NikeID. “Alex would never want us to see all the humiliations he must go through,” Robin says. She’s appalled by Kent’s comments—“Who is he to tell me how to raise my son? He doesn’t really know Alex”—and suspects there’s more to his sending Alex home. “Alex is competition for D.J. Clark Kent,” Robin says. “All the attention Alex gets, that’s attention D.J. Clark Kent isn’t getting.”

The attention Alex gets also bugs his 16-year-old sister, Zoe. “It’s annoying. That’s all I can really say about it … it’s just really annoying,” Zoe says. “I’m his older sister, and when I walk around the neighborhood people know me as ‘Oh, aren’t you that cool little kid’s sister?’ That’s really who they think I am: sister of the mayor of Nolita.”

“I said to him, ‘Alex, we’re not friends. We cool. But we’re not friends. You’re 13. I’m 40.’ ”

Her frustration with Alex is partly personal. “He won’t hang out with me anymore,” she says. On weekend mornings, Zoe and Alex used to go for breakfast together, then he got too busy. “It was never that great anyway,” she says. “It’s not like we got to have bonding time. He’d leave the table and talk to everybody in the restaurant.” (It wasn’t entirely horrible: “We’d always get a cup of free coffee or pancakes on the house.”)

But his big sister also wants to protect Alex as he weaves through the world. If you can’t choose between being a kid and being an adult, Zoe explains, you can be left stranded between the two. And what happens if all the attention dries up? Who will Alex be?

For now, Alex doesn’t seem too interested in Zoe’s concerns. He’s busy building his empire of connections. One night late this summer, we drove to a concert in East Hampton. James Taylor was playing. Alex had never heard of him, but it was a chance to meet A-listers and Alex didn’t want to miss it.

He was in fine form. First, he bumped into David Blaine, the magician, who was biting quarters with his hind teeth. Alex didn’t need an introduction; they had friends in common. Blaine made a card disappear for Alex. “So, what do you think of that?” he asked. Alex shrugged, unimpressed, and the crowd cracked up.

He moved on and stumbled upon Paul McCartney. “Hey, what’s your name, young man?” McCartney said. But Alex wasn’t interested in talking to a Beatle. “Aren’t there any professional athletes here?”

He looked around. A tall man passed. Finally, a ballplayer! Alex introduced himself. “This kid is mad cool,” said C.J. Miles, shooting guard for the Utah Jazz, within minutes of making Alex’s acquaintance. “He knows some of the same people we know from around the league.”

“C.J.,” Alex asked, “do you have your own plane?”

“Man, I don’t even have a house. You know how NBA politics are. I’m going to Europe,” Miles joked.

“You should go to Israel,” said Alex. “They bless basketballs there. Baruch ata Adonai, Elohenu melech ha’olam, boray peri ha swish. Swish! Swish!”

Miles and his friends slapped their knees. “Yo, this is the funniest kid ever.”

An entourage began to form. Miles, his friends, their friends. They followed Alex as he chatted up a group of models and the party promoter who brought them, and then back to the gourmet buffet, and then over to the espresso bar.

“You are so cute,” said the espresso girl, as Alex ordered his third decaf cappuccino. “Oh, I just want to marry him.” When she looked back over at Alex, she blushed. “That little shit, he’s blowing me kisses.”

Alex and his newfound posse were the last to leave the party. When he finally made his way to the parking lot, he was trailing two (stolen) potted plants—daffodils for his mom, fresh basil for the next morning’s omelette—four gift bags full of swag, and one NBA player and six of his friends. On the way out, he saw David Blaine drive by in his Bentley. “Hey, David,” Alex shouted. “Don’t bend my quarter!”

It was too early to call it quits, and Dune, the nightclub, was suggested as a next stop. “I don’t know if Al can get in,” one person said. Alex was offended. “If I can get into Bungalow 8, I can get into Doooone.”

By the time we arrived at the club, the line at the door was twenty deep. The beefy bouncer looked at Alex and shook his head. No way. Alex found a back door and knocked. Nothing. He found another door and knocked again, putting his ear close to listen. Nothing. Finally, Alex conceded defeat. “That club sucked anyway,” he said as he got back in the car. It was 1:30 in the morning. He rolled down the windows and turned up the music, as if ready for more. Then he fell dead asleep. Curled up in the passenger seat, he looked, for the first time that night, like a kid.