Before a Fatal Helicopter Crash, 2 Midair Breakdowns and Unpaid Bills

As federal investigators began the long job of examining what caused a sightseeing helicopter to crash into the Hudson River on Thursday, killing all six people on board, details began to emerge about the small company that made the doomed flight — and its operator’s checkered history.

Public records and interviews with pilots and other members of the helicopter industry showed that the company, which has operated as New York Helicopter Charter, had long been seen as an also-ran in the competitive business of taking tourists for aerial views of landmarks in and around New York City.

Its fleet was smaller and older than those of the biggest operators in the metropolitan area, where a single helicopter can earn up to $5,000 an hour.

Its owner and chief executive, Michael Roth, had developed a reputation for being slow to pay and quick to sue. After a sightseeing flight in 2013 ended in an emergency landing in the Hudson, Mr. Roth sued a company that had performed maintenance on its aircraft, saying it was to blame for the near disaster.

He accused the operator of one heliport in Manhattan of “ripping us off” and later sued the operator of another heliport to regain access there after being accused of failing to make good on past debts. He has also sued lenders over loan agreements, one of which he called “criminally usurious” in a court filing.

“He’s had disputes with everybody,” said John Kjekstad, a longtime sightseeing tour operator who said he has known Mr. Roth for 40 years. “That’s him.”

Even before the Covid pandemic wiped out tourism in New York, Mr. Roth’s company had fallen into tough financial straits. His company filed for bankruptcy in 2019 and had one its helicopters repossessed late last year, just eight months into its lease. Court records show that Mr. Roth reconstituted the business as New York Helicopter Tours after it failed under its former name.

Reached by phone on Friday, Mr. Roth said: “I can’t talk to you. Have a nice day.”

Mr. Roth has said he has been in the charter helicopter business for 30 years, dating to the 1990s, when there was less competition, and regulation, and a generally easier acceptance of helicopters as a mode of a travel in a crowded, urban area. He started New York Helicopter Charter in August 1998, state records show.

His company earned about $5 million a year from the 1990s well into the 2000s, financial records show. There were no reports of crashes or other distressing incidents involving the firm in those years.

The first public signs of trouble came in the 2010s, when aircraft operated by New York Helicopter Charter were involved in two incidents in the span of two years.

In 2013, a pilot ferrying a family of four Swedish tourists over the Hudson River heard a loud popping sound and began to lose power. As they descended toward the water, the pilot inflated pontoons that held the helicopter upright and he and the passengers escaped uninjured.

In 2015, another of its helicopters was lifting off from a base in New Jersey when the pilot began to lose control before he could set the aircraft back down. An investigative report of the incident described it as a “hard landing.” The pilot was not hurt.

By then, the airspace over the metropolitan area had become more crowded, prompting residents and their elected officials to press for limitations on the aerial sightseeing industry. Local officials urged the Federal Aviation Administration to curtail the flights or ban them altogether, citing excessive noise and fears of deadly collisions.

By Mr. Roth’s telling, New York Helicopter Charter was dealt a serious blow by a decision city officials made in January 2017 to reduce helicopter traffic. In court papers, Mr. Roth said that decision forced the company to cut the number of takeoffs and landings in half. At the same time, its landing fees at the Lower Manhattan heliport substantially increased, Mr. Roth said in court papers.

More recently, the company and its owner appear to have struggled financially, consistently failing to pay bills, according to records of lawsuits filed to collect debts and judgments from government agencies.

In October 2019, New York Helicopter Charter filed in Manhattan federal court for the Chapter 11 bankruptcy proceeding, which, in an effort for the business to become viable, can allow debtors to organize their financial affairs while continuing to operate.

As part of the case, Mr. Roth testified that the changes in city rules had a “substantial” effect on his business. The company, which cut its payroll from 30 employees to 13, planned to return to profitability by expanding operations in New Jersey and through a Miami affiliate, he added.

At the time, the company’s revenues appeared to be steadily declining. Its income had ranged from $4.6 million to $5.8 million a year since the 1990s, but it dropped to $3.9 million in 2018, and just $2.1 million in the first 10 months of 2019, according to filings in the bankruptcy.

The bankruptcy ended in 2022, leaving many creditors unpaid, but the financial problems continued. In 2024, Mr. Roth resolved two New York state tax liens totaling more than $70,000, and his company paid a $45,000 judgment from the New York State Workers’ Compensation Board, records show. But another workers’ compensation judgment, for $21,500, appears to have gone unpaid. Records indicate that a federal tax lien in his own name for more than $225,000 is also still outstanding.

A New Jersey media company that produced brochures for Mr. Roth’s new firm, New York Helicopter Tours LLC, sued that company last year over $35,000 in unpaid bills; an arbitrator awarded the media company $14,700.

At the time, the company was relying in part on a model of helicopter, the Bell 206, that has fallen out of favor with many tour operators, said Jack Cress, a former Marine Corps helicopter pilot who has worked as a helicopter crash investigator for 50 years. Originally produced for the United States military in the early 1960s, the 206 is smaller than its modern equivalents and can seat fewer paying passengers, Mr. Cress said.

He added that civilian tour operators often fly heavier payloads than does the military, and they also fly more often — placing the aircraft under more stress while exposing them to the waters of the Hudson River, which can force salt into the internal systems and cause corrosion.

Still, after emerging from bankruptcy, New York Helicopter appeared to be recovering. It added to its fleet by leasing a Bell 407 helicopter from PHI MRO Services, based in Lafayette, La.

In a July announcement of the transaction, Mr. Roth said, “This new helicopter will allow us to expand our capabilities and continue to provide world-class tours and charters to the New York area.”

He added that his company looked forward to a “long and continued relationship” with PHI MRO, and to making more additions to its fleet.

Five months later, PHI repossessed the helicopter, saying in a subsequent lawsuit that New York Helicopter had failed to make lease payments or to return the aircraft as Mr. Roth had said he would do. While disputing PHI’s bill, Mr. Roth sent an email that accused the company of failing to provide necessary parts. In all capital letters, Mr. Roth added a request to advise “WHERE YOU WOULD LIKE US TO DROP OFF HELICOPTER ASAP.”

PHI did not wait long for that delivery. On Dec. 13, the company “peaceably and without objection” took back its helicopter, it said in a court filing. Calls to PHI’s offices in Louisiana were not returned on Friday. Its lawsuit, seeking $1.5 million in damages from New York Helicopter, is still pending.

Mr. Kjekstad said the repossession of the Bell 407 was a definite setback for Mr. Roth’s business.

“The 407 is a better helicopter for what we do in our business,” he said.

One of Mr. Roth’s remaining helicopters was a Bell 206 L-4, built in 2004 and owned by a firm in Louisiana.

It was this helicopter that Agustín Escobar boarded on Thursday with his wife, Mercè Camprubí Montal, and their three children — Agustín, 10, Mercè, 8, and Víctor, 4 — for a tour over Manhattan. Mr. Escobar was the chief executive for rail infrastructure for the technology company Siemens, and his family was on vacation to celebrate Ms. Camprubí’s birthday.

At the controls was Seankese Johnson, 36, a U.S. Navy veteran who had started flying for New York Helicopter only this year.

Mr. Johnson and his passengers took off and looped around the Statue of Liberty, then cruised up the Hudson to the George Washington Bridge.

They had made it most of the way back to the heliport when the aircraft broke apart and dove into the water, killing everyone onboard.

Bianca Pallaro and William K. Rashbaum contributed reporting. Susan C. Beachy and Sheelagh McNeill contributed research.