Charles Stravalle, a New York State Liquor Authority investigator and retired police captain, knows when he’s being followed. And the black Chevrolet had been on his tail all day.

Even when he got home to Queens, after some 100 miles on the road, the Chevrolet’s driver remained camped out in front of his house with a camera.

Mr. Stravalle called the police, who later pulled over the private detective on the Long Island Expressway, according to an account Mr. Stravalle gave to the New York Department of State, which regulates members of the profession.

In court papers filed this week, MSG Entertainment acknowledged it had hired a private eye, which it called “a common and lawful practice.” Officials later said they did so to tail Mr. Stravalle.

James Dolan, the head of the company, has made headlines for using facial recognition technology to identify and bar lawyers working for firms suing his company. That prompted the State Liquor Authority to assign Mr. Stravalle to help investigate whether the ban broke state beverage laws that require establishments to admit the general public.

Mr. Dolan’s legal team hit back by investigating the investigator, setting up the Queens encounter worthy of a pulp novel.

It is the latest episode in an increasingly pitched battle between Mr. Dolan, who is a billionaire’s son, and a part-time civil servant working a $33-an-hour job. Mr. Dolan has mocked authority officials as corrupt hacks looking to deprive Knicks fans of beer.

Mr. Dolan, whose company owns Madison Square Garden, as well as the Knicks and Rangers and numerous venues around the city, has rarely shied from petty battles, whether with fans who have criticized his stewardship of the Knicks, or with the basketball team’s former forward Charles Oakley, a critic whom Mr. Dolan once had ejected from the arena.

This latest dispute comes at a critical time for Mr. Dolan. State Liquor Authority violations against Lavo, a nightspot belonging to MSG Entertainment’s Tao Group, come as Mr. Dolan is trying to sell that subsidiary to help finance the construction of MSG Sphere, a $2.2 billion entertainment venue in Las Vegas.

Madison Square Garden’s license to operate a sports arena in New York City expires in July, and Mr. Dolan is looking for city officials to renew it permanently — a matter of intense debate. At the same time, the New York State Senate is trying to revoke the Garden’s $43 million-a-year property tax exemption.

Amid the rising government pressure, the State Liquor Authority has emerged as a focal point for Mr. Dolan’s ire. But the cloak-and-dagger antics in Queens are an escalation in the feud. And they are sowing alarm among state officials.

The morning after Mr. Stravalle reported the tail to the police, an authority official sent a warning about the private eye to State Senator Brad Hoylman-Sigal of Manhattan, who is championing the drive to end the tax break.

“Seems prudent to keep an eye out when you’re out,” the official texted, according to a copy shared with The New York Times. “He was cited for possession of a weapon, a knife in excess of the permissible length.”

“It’s intimidation tactics, full stop,” Mr. Hoylman-Sigal said in a subsequent interview. “And it’s objectionable on its face.”

“James Dolan is using the money he receives as a tax break to hire private investigators to intimidate public officials,” he added.

Mr. Dolan’s team portrays its private eye, and itself, as victims of a brazen act of government overreach.

In a petition filed with the State Supreme Court in Manhattan seeking to have state sanctions overturned, MSG Entertainment claims that the liquor authority “in record time” asked the Department of State, which licenses private detectives, to “threaten” the investigator.

Department officials, at the behest of the authority, said they would revoke his license if he didn’t disclose “confidential information about his client, details about the work he had done and the reasons for his investigation,” according to the petition filed this week.

A State Department spokeswoman called the questioning routine but declined to comment further.

Mr. Dolan described the State Liquor Authority as “gangster-like.”

“MSG didn’t start this,” said Jim Walden, the company’s co-counsel. “What is happening at the S.L.A. is just improper. It is a bureaucracy out of control.”

Company officials insist the private investigator was hired to see whether Mr. Stravalle, who also holds a private investigator’s license, was engaged in any outside work that might have constituted a conflict of interest with his Garden investigation.

Bill Crowley, a spokesman for the State Liquor Authority, said that agency policy prohibits employees from “performing any services for, or have any interest direct or indirect in, any business involved in the manufacture, sale, transportation or storage of alcoholic beverages.”

The State Liquor Authority, as well as New York City’s Police and Health Departments, began looking at Lavo after a slashing there in February, the authority said.

Mr. Stravalle found more than 30 violations at the trendy Manhattan nightclub, ranging from unsanctioned fireworks to a meat slicer “encrusted with old food.” The club also failed to grant access to a video of the attack.

Mr. Dolan’s petition accused Mr. Stravalle of waging a “harassment campaign” against his company and of being “combative and antagonistic” when interviewing him.

The petition also disparaged Mr. Stravalle’s record with the Police Department from 20 years ago, claiming that “questions were raised about crime statistics reported in the precinct where he had been the commanding officer.”

Mr. Stravalle declined to comment for this article.

Chelsea Binns, who has worked as a private investigator in New York and is an assistant professor at John Jay College of Criminal Justice in Manhattan, said she knows of no state limitations on using private eyes to tail state officials — though she personally would not do so without consulting a lawyer.

“Anyone can just whip out their camera and start filming,” Ms. Binns said. “And it can make anyone uneasy, but that’s the times we live in, unfortunately. The difference between an everyday citizen doing it and a P.I., is the P.I. is actually licensed to do it.”

Mr. Dolan first started using facial recognition technology to enforce the lawyer ban last year at the Garden, as well as at the Beacon Theater and Radio City Music Hall, which are also owned by MSG Entertainment. In the petition, the company estimated that the ban affected “less than 1 percent of all lawyers in New York.”

The State Liquor Authority began looking into the Garden in November.

Mr. Dolan responded during a television interview in January. He threatened to stop selling beer at a coming Knicks or Rangers game as a show of contempt for the authority. And he taunted its chief executive, Sharif Kabir, by holding up a flier bearing his photo and contact information so thirsty fans might “tell him to stick to his knitting.”

The next month, the authority charged MSG Entertainment with three more violations, this time in connection with the lawyer ban at the Garden, the Beacon and Radio City, as well as a fourth for an unapproved change to its corporate structure, said an agency spokesman, Josh Heller.

The charges will now go to a hearing and the authority’s board may determine disciplinary actions, which could include fines, cancellation, suspension or revocation of liquor licenses.

If Mr. Dolan decided to cooperate, it “would in all likelihood prevent any chance of the licenses being suspended, canceled or revoked,” Mr. Heller said.

Of course, that would involve giving up the lawyer ban, which Mr. Dolan does not seem willing to do.

In Mr. Dolan’s corner is Randy Mastro, a pit bull of a lawyer who served as a chief of staff and deputy mayor to Mayor Rudolph W. Giuliani in the 1990s. Mr. Dolan also recently hired as a consultant Hope Hicks, who once served as President Donald J. Trump’s communications director in the White House.

Mr. Stravalle, however, is no pushover. Raised in Queens, he retired as a captain from the Police Department in 2005 after an accomplished career and two master’s degrees. He worked in leadership positions and on some of the most challenging details after starting on patrol in housing projects and crack-ravaged neighborhoods in the 1980s.

He is known in the industry as a tough but fair investigator who knows the beverage code thoroughly, said Robert W. Romano, a Manhattan-based lawyer who represents dozens of clients in dealings with the State Liquor Authority.

“He’s more thorough than any investigator I’ve ever seen,” he said. “He’s tough on everybody.”

Kirsten Noyes and William K. Rashbaum contributed reporting.

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