The trouble began in August 2021, according to the claims in an unusual lawsuit filed in July, when Theodore Weintraub was 17 and attempted something of an American rite of passage: buying alcohol with a fake ID.

He tried, and failed, many times. But instead of going into a bodega or Midtown dive bar, he repeatedly chose the bar in one of Manhattan’s most exclusive hotels, attached to a restaurant run by the celebrity chef Jean-Georges Vongerichten, where a cheeseburger with fries costs $60.

Bartenders don’t see too many teenagers flashing fake IDs at establishments with a $14,500 bottle of wine on the menu, so Mr. Weintraub stood out. Again and again, staff members refused his increasingly aggressive attempts to buy a drink, the lawsuit said, until finally, in 2021, the hotel banned him entirely.

What happened next was at first annoying and then disruptive and eventually led to a series of events so bizarre and disturbing that the hotel, The Mark on East 77th Street on the Upper East Side, sued Mr. Weintraub, now 19, for defamation.

According to court papers filed late last month, Mr. Weintraub returned to The Mark earlier this summer, two years after his banishment, on a quest for revenge. It is unclear why he waited for two years to return, and he declined requests for comment.

Mr. Weintraub and another man, referred to as John Doe in the legal filings, became fixtures outside the hotel, the suit contends, chanting and holding protest signs saying “The Mark Denies the Holocaust,” “The Mark Spreads Disease” and “The Mark Supports Epstein,” in reference to Jeffrey Epstein, the convicted sex offender.

According to the lawsuit, first reported by Patch.com, they physically accosted hotel guests until, finally, a video shows, a sidewalk brawl erupted in July between the protesters and fans of the rap star Drake, who was staying at the hotel.

The Mark is near Mr. Weintraub’s home. But beyond its proximity, it is unclear why he would decide to try to buy alcohol there, or why he would keep trying after he was repeatedly refused service. The hotel’s account in court papers suggest that he harbored a grudge for years until it finally boiled over.

Approached by The New York Post last week, Mr. Weintraub was taciturn.

“I can’t comment now,” he said. “The truth will come out.”

Only a few weeks after Mr. Weintraub was banned in 2021, he was back at the hotel — this time with his unsuspecting parents.

Mr. Weintraub’s family had made a dinner reservation at the restaurant, but they were stopped from taking their seats by security, who informed them their son was not allowed on the property, according to the lawsuit.

This appeared to be news to Mr. Weintraub’s parents. The teenager first asked the hotel to forgive him, the lawsuit said, but soon flew into a rage, screaming that the hotel was antisemitic and that its employees spat in people’s food.

The young man’s father, Dr. Philip J. Weintraub, a cardiologist, calmed him down and told hotel staff that “he understood the ban,” according to court papers.

Dr. Weintraub — an art collector who made tabloid headlines himself in 2021 over an insurance dispute that centered on the theft of $1.5 million worth of art from his roughly $7 million collection — handed hotel staff members his business card and told them to call him directly if his son caused any further trouble. He did not respond to requests for comment.

That appeared to have been the end of the dispute until earlier this summer, when staff members said they ran into Mr. Weintraub again on the sidewalk near the hotel, where he screamed at them, according to court papers.

Soon, Mr. Weintraub and another man began their protests. By July, they were also screaming insults at hotel staff, including repeatedly calling one doorman a pedophile and yelling that “his mother is a prostitute.” The lawsuit charges that they also physically confronted guests.

On several occasions, the hotel called 911. So did Mr. Weintraub and the other protester.

Crystal, a hotel employee who spoke on the condition that she be identified only by her first name because The Mark told its employees not to speak to the news media, said she had seen Mr. Weintraub and another man sit in a black SUV — a Cadillac Escalade, according to the court papers — outside the hotel and give instructions to the protester.

She said she wished Mr. Weintraub would spend his time and money on other pursuits.

Things reached a fever pitch when Drake stayed at the hotel last month. In one video posted online by The Hollywood Fix, a celebrity gossip site, a man can be heard chanting “The Mark helped Epstein!” as Drake and his entourage leave the hotel.

The lawsuit said that a melee erupted outside the hotel when Mr. Weintraub and his fellow protester tried to keep a celebrity, who was unnamed in court documents but whom the video shows to be Drake, from re-entering the hotel. That resulted in the other protester “being punched in the face by fans” of the celebrity, according to the suit.

The celebrity, who is Jewish, later complained to hotel management that he was disturbed to hear someone screaming about Holocaust denial as he tried to come and go from the hotel, the lawsuit said.

Edward, the superintendent of a nearby commercial building who asked to be identified only by his first name for fear of losing his job, said he had seen Mr. Weintraub and his protest companion “get in arguments with Drake’s bodyguards a couple times.”

But the superintendent also said he viewed Mr. Weintraub’s crusade as more of a New York City oddity than a genuine menace.

“As far as crazy things we’ve seen, this rates a 2,” he said. “We see a lot around here.”

The hotel’s managers were more accustomed to hosting celebrities and the super rich — The Mark once charged $75,000 per night for its penthouse suite — than seeing street fights on its sidewalk. By the end of July, they were fed up.

Late last month, the hotel filed the lawsuit against Mr. Weintraub for defamation, and on Thursday it filed for a restraining order that would prevent him or anyone acting on his behalf from picketing outside the hotel.

The request for a restraining order also addressed some of the specific claims made by Mr. Weintraub: It would prevent him from publicly claiming The Mark denied the Holocaust, supported Jeffrey Epstein, supported sexual assault or was a known source of infectious disease.

In an affidavit, Etienne Haro, the hotel’s general manager, took particular umbrage at Mr. Weintraub’s charges of Holocaust denial and collusion with Mr. Epstein, who Mr. Haro said had never even stayed at The Mark. (He lived six blocks away before he was sent to prison, where he died by suicide in 2019.)

“The notion that we deny the Holocaust is a spurious attempt to damage our reputation and relationships,” wrote Mr. Haro, who said the hotel’s prestigious reputation “can be damaged, as here, by a single person loudly complaining about our business integrity.”

Employees of the hotel declined to comment.

Alex Weisenberger, 40, who works on the block in the art industry and uses they/them pronouns, said they had seen Mr. Weintraub protesting outside the hotel and assumed it was a prank. Mx. Weisenberger said others in the neighborhood seemed unfazed.

“I just saw him walking back and forth in from of The Mark, chanting, ‘The Mark has Rats,’” said Mx. Weisenberger.

“It was weird, but people didn’t really seem bothered,” they added. “Obviously the hotel staff huddled to talk about what to do. But there were people sitting outside eating at tables, and they just kept eating.”

Wesley Parnell contributed reporting.