Jet travel, yacht adventures, and more. How Steward’s CEO used corporate funds as the company crumbled.

Steward Health Care CEO Ralph de la Torre and his top deputy jetted last summer to Jamaica for an escape from the scorching heat in Dallas. Among the worries they left behind: the unpaid bills that were piling up at headquarters.

They stepped off the company’s private plane and onto de la Torre’s personal yacht, bound for a weeklong cruise through the Caribbean. They followed that trip with a few days back in the office. And then de la Torre headed to the Virgin Islands on another break.

And then another — and another. Jamaica, Antigua, St. Kitts, Bermuda, Turks and Caicos. In all, the CEO spent 34 days in the tropics — plus a long weekend in the French Riviera — last summer as his health care company teetered on the brink of bankruptcy, according to a new Globe Spotlight Team analysis of public flight records, yacht records, internal company documents, and interviews with people close to the matter.

Nearly half of the 582 flights flown in 2022 and 2023 were to or from destinations more than 100 miles away from any official Steward location, such as hospitals or corporate offices. Passengers included de la Torre’s fishing friends, a luxury yacht salesman, and high-profile horse trainers.

De la Torre flew to Massachusetts — the birthplace of his company and then home of eight of its hospitals — just seven times in two years, records show. Each trip lasted a day or less.

In many, if not all, instances, the private jet excursions were paid for by Steward, records show, the funds pulled directly from the coffers of one of the nation’s largest — and most troubled — for-profit, private hospital chains.

De la Torre’s personal spokesperson, in a statement to the Globe, confirmed that the executive was paid for such travel and noted that de la Torre views the benefit as supplemental to his pay.

“For safety reasons, Dr. de la Torre elected to use the plane as part of his compensation rather than receive a substantially higher salary,” Rebecca Kral said.

By the time de la Torre returned to the office last September, unpaid vendors had repossessed medical supplies across the hospital chain, putting lives at risk. A recent Spotlight investigation found at least 15 cases in recent years in which Steward patients died after failing to receive professionally accepted standards of care due to equipment issues or staffing shortages.

The use of the company’s jets raises a host of legal questions about corporate disclosures and possible tax avoidance.

“When you’re at the point where the company jet is at the disposal of third parties who are not employees or there’s no business purpose for the flight, it is going to get very tricky for the accountants to classify that as a legitimate expense,” said David Yermack, a finance professor at New York University and author of two papers on executive jet use.

In February, the IRS announced a crackdown on large corporations and high-income taxpayers who use business jets for personal reasons. Federal tax code allows a corporation to deduct money spent maintaining a corporate jet — but only if that plane is used for business use.

A Steward spokesperson responded to a list of questions from the Globe by saying the company has no comment.

Last week, de la Torre failed to appear before a Senate committee investigating the implosion of his health care chain. The committee voted Thursday to hold the executive in contempt of Congress, referring him for civil and criminal charges over his refusal to testify.

The Spotlight Team previously reported that de la Torre often used Steward’s bank accounts as his own; to purchase and renovate an 8 million euro apartment in Madrid; to donate millions of dollars to his children’s prep school; and more. Some of these transactions are now under scrutiny by a federal grand jury in Boston, people close to the matter have told the Globe.

This new Globe analysis rounds out a globetrotting portrait of how de la Torre and other executives spent their time — and the company’s money — in the months and years before it went under.

De la Torre almost exclusively used the company’s Bombardier Global 6000, the more lavish of the two models.

Another jet — the slim Dassault Falcon 2000 – was used mostly to fly other Steward executives throughout the United States and Acosta to Costa Rica, records show. The one exception: the summer of 2022, when both jets were used to ferry guests to de la Torre and Acosta’s wedding on the Amalfi Coast.

In the released statement, de la Torre’s spokesperson said the executive’s contract “incorporates the personal use of corporate jets.” She did not address questions about specific flights or travel by de la Torre’s and Acosta’s friends and associates. Nor did she respond to questions about de la Torre’s awareness of Steward’s financial woes amid his non-business travel.

The spokesperson noted that the locations in which Steward hospitals operate or seek to operate carry significant security risks and threats of “terrorism, high levels of violence, and kidnapping of high-net worth individuals.”

“A third-party private security consulting firm strongly recommended that he and his family use private transportation, including private air travel, for safety reasons given ‘the threat profile the head of a major health care system inherently faces.’”

The statement continued: “To be clear, his use of the corporate plane not only counted as compensation but was also taxed appropriately. Further, as we have said before, it is highly inaccurate to say or imply that the costs of the plane were born solely by Steward Health Care. Two other entities, including Steward International contributed significantly to these costs.”

Steward’s global entity, Steward International, was registered first as a company in Delaware in 2017, with de la Torre and Callum listed as managers. The Globe has previously reported that Steward executives regularly mixed funds among the entities, and that the companies are not as separate as executives claim.

A super midsize jet such as the Falcon costs roughly $1,900 an hour to operate, according to experts contacted by the Globe. The Bombardier runs closer to $2,700 an hour. At those hourly rates, roughly half a million dollars were spent flying Steward jets to and from Costa Rica from 2022 to 2023.

“One has to wonder,” said Bernard Black, a professor at Northwestern University with expertise in corporate governance. “Did the board know about all this and really think it was a good use of company funds? And how much time did this guy spend doing work?”

Khadija Sharife of the Organized Crime and Corruption Reporting Project contributed to this report.