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A few days after Hurricane Maria leveled Puerto Rico, John A. Paulson, the billionaire hedge fund manager, boarded his company's 23-seat Bombardier jet and flew to San Juan.
Mr. Paulson wanted to check personally on several resorts and a large office building that he and his firm own, two people familiar with the trip said. He traveled when commercial air traffic to the devastated island was limited and most private jets landing in San Juan were required to bring badly needed emergency supplies.
Mr. Paulson's quick trip is an indication of just how much big investors have riding on the future of the Caribbean island.
Mr. Paulson and his firm, Paulson & Company, have invested hundreds of millions of dollars there as he, along with many of the best-known names on Wall Street, bet big on taking advantage of a long period of depressed prices for luxury properties and other real estate. Their wagers are looking increasingly unlucky, especially after the storm.
Moody's Analytics, an economic forecasting firm, estimates that the hurricane could cost Puerto Rico up to $95 billion in damage and lost economic output. It could take months, even years, for parts of the island and its 3.4 million residents to recover from the storm, which destroyed much of its electrical grid and left millions without running water or reliable mobile phone service.
Mr. Paulson, who served as an economic adviser to Donald J. Trump during the presidential campaign, has been particularly outspoken in his support of the island as an investment opportunity. Other companies that went to Puerto Rico in search of bargains included the Blackstone Group, the Och-Ziff Capital Management Group, the D. E. Shaw Group, Fundamental Advisors, Goldman Sachs, Lone Star Funds and Monarch Alternative Capital. The main attractions have been hotels, condominiums, office buildings and distressed real estate loans.
Few tears will be shed for financial losses borne by wealthy investors who gambled on Puerto Rico, especially those like Mr. Paulson, who made billions off the 2008 collapse of the United States housing market.
But the interests of these investors and the Puerto Rican economy might be aligned. Tourism supports more than 60,000 jobs in Puerto Rico. Luring deep-pocketed investors from the mainland has the potential to hasten the island's recovery.
At the moment, though, those investors are staring at hard-to-quantify red ink.
"We sustained a lot of damage, and we're facing very significant losses," said Brian Tenenbaum, regional director for the Morgan Reed Group, which owns or operates several office buildings, commercial buildings and residential complexes on the island.
Samuel Kirschner, chief operating officer with CPG Real Estate, which has been investing in commercial and residential properties in Puerto Rico for nearly 18 years, has struggled to get his properties open because of damage from the storm. After chartering a private plane from Fort Lauderdale, Fla., with canned goods, diapers and batteries, CPG managed to partly open an outdoor shopping plaza in San Juan. The idea was to give residents a place to drink, eat and cool down.
"We're going to lose a lot of money opening it now," Mr. Kirschner said.
The Puerto Rico Tourism Company lists at least seven hotels closed with no clear reopening date. About two dozen expect to begin taking reservations before the end of October. Some resorts are said to have suffered little structural damage but severe damage to their beaches and grounds. Tourists might balk at returning to the island anytime soon.
"The turnaround was set back years," said David Tawil of Maglan Capital, whose firm used to hold Puerto Rican debt.
Even before Hurricane Maria, Puerto Rico's economy was ailing, with 45 percent of the population living in poverty. In May, Puerto Rico effectively filed the largest-ever federal bankruptcy proceeding by a local government, and much of Wall Street's attention has focused on the creditors who hold some of Puerto Rico's $74 billion in public debt.
On Tuesday, the bondholders, including big investment firms such as OppenheimerFunds, the Baupost Group and Tilden Park Capital Management, got a jolt when President Trump said some of Puerto Rico's debt might have to be wiped out — a comment that sent the price of those already distressed bonds plunging. Prices stabilized after the White House clarified that the administration was not planning to interfere with the bankruptcy process.
The pool of bond investors — many of which bought Puerto Rico's debt at deeply distressed prices — is different from those that plunged into real estate. But both camps are now betting that insurance payouts and aid from Washington will speed the commonwealth's recovery and increase the value of their investments.
"I think a lot of money will be spent fixing Puerto Rico, and that should be better for everyone," said Marc Lasry, a founder of the Avenue Capital Group, a hedge fund that owns some of Puerto Rico's debt.
Some investors are calling for an ambitious federal rescue package — an initiative that would help both the island and the investors' bottom lines.
"The electrical grid has had catastrophic damage, and Congress is going to need a major relief bill," said Adam Greenfader, who runs AG&T, a company that owns a number of lower-income housing complexes on the island. "Many people will leave if things don't get turned around quick enough."
As for Mr. Paulson, two of his resorts — Condado Vanderbilt Hotel and La Concha Renaissance San Juan Resort — suffered minimal damage and are housing federal relief workers and hotel employees whose homes were damaged. Federal workers are being charged a negotiated rate, while employees are staying at no cost. A third resort, St. Regis Bahia Beach Resort, is currently closed.
In a statement, Paulson & Company said, "We look forward to welcoming guests as early as the winter season."
Mr. Paulson's firm, which once managed $36 billion, has shrunk to just under $10 billion after a series of bad trades in recent years. This year, several of his funds have suffered further losses. Mr. Paulson has trumpeted his wager on Puerto Rico as a crucial part of his long-term investment strategy.
Mr. Paulson, speaking at an investment conference last year, compared Puerto Rico to Miami in the 1980s, when Miami had many abandoned buildings and vacant lots.
He predicted: "Looking back five years from now, this will look like an extraordinary opportunity."