Eduardo Elsztain thought he could succeed where dealmakers like Jared Kushner, Patrick Drahi and Matthew Bronfman didn’t: In Israel, the land of his business dreams.

The Argentine businessman has achieved plenty elsewhere. Back in 1990, it took him just an hour to persuade George Soros to give him $10 million to invest. He parlayed that and other investments into a holding company that by 1997 had made about $360 million in acquisitions. Then he and Soros picked up 25 percent of Argentina’s largest state-run mortgage bank in a privatization that ultimately gave them management control.

But in the Jewish state, he has spent five years and almost $700 million trying to turn around IDB Development Corp., Israel’s largest conglomerate. There’s no telling whether he’ll pull it off. He needs to sell a key asset to help repay $1.5 billion to debtholders in the next three years—while fighting regulators’ demands.

“Most people told me ‘Beware: you’re going to Israel and you will lose money.’ I heard it 1,000 times,” Elsztain, 57, said over a kosher breakfast at Bloomberg headquarters in New York in April, adding that he’s seen worse conditions in Argentina. “We are committed to this investment.”

If Elsztain succeeds, he’ll be turning recent history on its head. About 10 wealthy foreign Jews have foundered in Israel in the past few years, either paying too much for assets, or getting into conflict with regulators and partners, or walking away from deals.

An investor group headed by Bronfman, of Seagram liquor fame, sold out after 10 difficult years as majority shareholder of Israel Discount Bank. French billionaire Drahi helped start a mobile-phone price war that has dragged down the entire industry. And the presidential son-in-law’s Kushner’s Funding LLC walked away from talks to buy one of Israel’s biggest insurance companies in 2014 after Jared Kushner got a closer look at the country’s regulatory environment.

Representatives for Kushner Companies, Drahi’s Altice SA and Bronfman all declined to comment.

Such investors often don’t understand that without the help of local partners, their success at home doesn’t travel smoothly to Israel, said Rafael Gozlan, chief economist at Israel Brokerage & Investments Ltd., an institutional investor and IDB bondholder.

That’s increasingly true. The Jewish state has fallen 23 spots in the World Bank’s Ease of Doing Business Index in the last six years, to 52nd of 190 countries. One reason: Prime Minister Benjamin Netanyahu’s coalition has pumped out a host of consumer-protection laws since 2011, when Israelis protested against the rising cost of living and widening inequality. The consequence has been more regulations on business.

“You have to learn the rules of the game,” Gozlan said. “Maybe in Israel you need that more.”

Elsztain says regulators remain just a temporary roadblock for IDB—which he calls a “gift from heaven.”

Meanwhile, he’ll have to sell IDB’s $470 million stake in Clal Insurance Enterprises Holdings Ltd. to comply with a law to reduce business concentration. Israeli regulators thwarted his previous attempts to sell to Chinese investors, then ordered IDB to unload blocks of the shares on the local stock exchange every four months. Elsztain said would lead to a 40 percent loss in the value of his investment. He wants two more years to find a buyer.

Elsztain’s complaints “remind me of when J.P. Morgan argued against selling his stakes in his monster conglomerates—I don’t think anyone would say that the U.S. was over-regulated,” said Dror Strum, Israel’s former antitrust commissioner. “Many people are really complaining about regulation that would prohibit them from doing things they’d be prohibited in other countries as well.”

Israel’s finance ministry, which oversees the sale of Clal, didn’t respond to a request for comment.

Elsztain, who had been investing in Argentine real estate, was taking a year off in New York in 1990 when a contact arranged a meeting with Soros. Over the course of an hour, Elsztain described the investment opportunities in Argentina. When Soros asked him how much money he was willing to manage, Elsztain said $10 million. “OK,” Soros replied.

“That’s how we worked,” Elsztain said. “He gave me the freedom to invest all over the world.” A Soros spokesman confirmed the story.

From his real estate empire in Argentina to the iconic Lipstick building in New York, a mining company in Australia and now IDB in Israel, Elsztain’s interests span the globe through his holding company, Inversiones Financieras Del Sur SA (IFISA). His net worth is approaching $600 million, according to Bloomberg calculations. A spokesman declined to comment.

Cultivating ties with top politicians has been one of his hallmarks. In 2012, former Argentine President Cristina Fernandez de Kirchner secured the biggest state-backed mortgage program for Banco Hipotecario SA, which is majority owned by the government and which Elsztain manages. A week after sitting with Bloomberg in New York, Elsztain gathered some of Argentina’s wealthiest people at Llao Llao, his five-star resort in Patagonia, to receive a two-day briefing from the interior minister and others about President Mauricio Macri’s planned tax reforms, according to four people present at the meetings.

Elsztain became interested in orthodox Judaism after his first visit to Israel at the age of 20; his time in New York deepened his faith. He built a backyard connection between his house and an adjacent synagogue in Buenos Aires for ease of entry. Business was part of the package: He invested in some Israeli companies in the 1990s. By 2012, he wanted more.

The opportunity was textbook Elsztain: IDB was drowning in debt when he took it over in the wake of the financial crisis. But it still controlled major assets, such as the country’s biggest supermarket chain and mobile operator.

First came trouble with his partner, Mordechai Ben-Moshe. Elsztain bought him out for 152 million shekels ($43 million) in 2015 after they squabbled over strategy.

Elsztain, through a spokesman, attributes the “deteriorated” situation of some of IDB’s operating units as well as pressure from bondholders as the reason for the split with Ben-Moshe. Through his spokesman, Ben-Moshe declined to comment.

Then came trouble with the government over the Clal stake. IDB agreed to a timetable for the forced sale, but Elsztain has since irked regulators by telling them he doesn’t want to divest the holding, according to three people close to the matter. IDB threatened to sue its government-appointed trustee last year to delay the stock-divestiture process.

Through his spokesman, Elsztain denied there is any bad blood with the ministry. JPMorgan Chase & Co. is advising IDB on the sale.

“Babysitting a company in crisis” is how Elsztain describes his time at IDB until now. Things are looking up, he says.

Clal shares have jumped about 20 percent this year on the expectation that rising interest rates will improve the returns of the insurer’s investments. Shufersal Ltd., the supermarket chain, boosted 2016 profit to the highest levels in five years.

IDB bought some time by selling five percent of Clal last month to an investor, who has agreed to sell back the shares to Elsztain when a buyer is found for the entire stake. The company said it has filed an appeal to Israel’s high court challenging a recent ruling in favor of the forced sale’s timeline. The next bloc offering is slated for early September.

“Is the company out of the woods yet? No,” said Yaniv Pagot, head of strategy at Ayalon Group, an institutional investor in Ramat Gan, Israel. It holds IDB bonds. “Elsztain has put in real money, and a lot of it. He’s not a magician, but without him there wouldn’t be an IDB.”

—With assistance from Gabrielle Coppola and Hannah Dormido.

This article was provided by Bloomberg News.