Sheldon Adelson spent more on Jewish causes and pro-Israel politicians than anyone in his generation. Liberal Jews never forgave him for it.

Modern Jewish history is in no small measure a tale of philanthropy. The image of the wealthy Jew who spends some of his riches on his people has its origins in the pre-Enlightenment era, when prosperous Jewish merchants were called upon to ransom their co-religionists or to buy favor for endangered tribe members from hostile rulers. As Jews began to play a more integral role in the economic and political sectors of societies in which they had previously been marginalized, they helped husband great achievements in science and culture. So deeply engrained in Jewish culture is the concept of tzedekah—the positive obligation to do justice via charity—that philanthropy has come to be expected from those Jews with the means to help others. Such givers were integral to the beginnings and triumph of Zionism, were critical in the rescue of endangered communities in the 20th century, and were the founders of the communal and fraternal institutions that served and perpetuated Jewish life in America.

They were fawned over and celebrated—the Rothschild family, Moses Montefiore, Felix Warburg, Jacob Schiff, and dozens if not hundreds of prosperous local families across the Jewish world. But they also engendered envy and resentment from other Jews for taking on the roles of intercessors for Jewish communities. And those who choose today to do what they can for their fellow Jews by interceding directly with governments and trying to affect policy now find themselves criticized or even reviled by their fellow Jews in a manner that their predecessors were not.

Such a person was Sheldon Adelson. The billionaire casino owner who died on January 11 at the age of 87 was in many ways a throwback to the magnates of the 19th century. His rags-to-riches story would have inspired unstinted admiration in earlier eras when the idea of a boy from the lowest economic stratum working his way to great wealth with a combination of smarts, pluck, and good luck was seen as a symbol of all that is great about America. But Adelson’s passing was instead greeted with a torrent of abuse from liberals in both the United States and Israel.

Sheldon Adelson gave more to Jewish causes than any other philanthropist in the first decades of the century. But rather than being chiefly remembered for this, media reactions to his death focused more on the money he had spent on aiding the campaigns of Republican candidates he saw as friends of Israel. And these responses were punctuated with tongue-clunking about how Adelson used the access he had acquired with his wealth to lobby not just Congress but presidents and prime ministers with an unabashed zeal for bending them to his will on issues related to Israel’s security.

Unlike most billionaires, he eschewed fashionable causes such as those associated with the environment and global warming. Short, stout, and looking every bit the product of a working-class background, Adelson had little interest in playing the role of a cool and fashionable member of the elite. And while he lavished donations on a host of medical institutions, he was most interested in funding Jewish life and Israel. Adelson was a traditional Zionist who believed in Jewish rights to the land and wanted them to be respected by its American ally.

And so, in addition to many mainstream non-political Jewish causes, he also gave to those institutions associated with nationalist and right-wing Jews. Vilified by an Israeli media establishment that leaned as hard to the left as its American counterparts, he responded by founding a free newspaper—Israel Hayom—that not only broke the liberal monopoly in that field but became the most widely read in the country.

For all this, he was hated in a way that parallels the obsession the right has with George Soros, the billionaire Jewish financier who, to advance left-wing causes, including those that are fervently opposed to Jewish interests and Israel, has spent even more on politics than Adelson did. Still, the position that Adelson occupied was unique. While his dedication to Jewish projects endorsed by a broad community consensus—such as the Birthright Israel program that has sent hundreds of thousands of young American Jews on free trips to the Holy Land—was unmatched by more centrist donors, long before his death he had become the symbol of conservative political donors who were determined to get their way. And he became the most prominent example of what Israel’s foes see as the sinister way the Jews have bought influence in Washington.

In that way, mainstream outlets like the New York Times considered Adelson’s death a political event more than anything else as they speculated whether his heirs or anyone else would play the same role he had in funding a particular type of Republican who is devoted to Israel.

But lost amid the politics is something more basic. Unlike virtually any of his contemporaries, Adelson was willing to push himself into the corridors of power and speak up for his beliefs when others would have pulled back. He clearly saw himself as someone placed in a position—thanks to his good fortune in business—to do something other than fitting in and playing along. In doing so, he may have earned criticism, but he also accomplished as much if not more for the Jewish people—whether grateful or not—than any of the other great philanthropists in his people’s history.

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ADELSON was born in Boston in 1933, the son of an immigrant cab driver from Lithuania and a mother who had immigrated from England. The family lived in a two-room flat where the children slept on the floor. He would later recall fighting Irish Catholic kids in Dorchester on the way to school, at a time when anti-Semitism was still very much an element in American life. But the young Sheldon’s priority was to work at getting ahead. Rather than merely holding after-school jobs, his journey as an entrepreneur began at 12 when he acquired a license to sell newspapers. At 16, he borrowed money from his uncle to start a candy-vending-machine business.

After a brief stint at City College in New York and service in the U.S. Army, his career as a serial entrepreneur began in earnest. He made a living selling toiletry kits, windshield de-icers, and magazine ads. Eventually he moved up to more lucrative concerns like selling condos and brokering mortgages and arranging chartered tours. By the time he was 40, he had become a millionaire, though along the way he had already made and lost his fortune twice.

His financial breakthrough came in 1979 when he and four partners created the Las Vegas COMDEX computer trade show. With computers beginning to dominate American commerce, the timing was perfect, and the profits from what became the most popular technology exhibition rolled in. By the time he sold his controlling share in the 1990s, it would net him half a billion dollars.

But long before then he had shifted his focus to revolutionizing the casino business. In 1989, he purchased the Sands Hotel and Casino, best known as the hangout for Frank Sinatra and his Rat Pack. Putting to use his previous experience in promoting trade shows, he added a convention center, an idea that transformed the Sands from merely a legendary gambling den into a thriving big business.

Not satisfied with that innovation, he and his second wife were inspired by a honeymoon trip to Venice to come up with the concept of combining gambling with more traditional family-oriented tourism—in this case, a Disneyland version of the Italian city. He spent $1.5 billion to build the Venetian, which opened in 1999. The idea not only paid off but led him to venture abroad to create, after difficult negotiations, similar but far larger versions of the same idea in Macao, China, and then Singapore.

His casinos turned Adelson into a multibillionaire. The exact amount of his vast wealth would fluctuate as economic cycles went up and down. But by the time he died, Forbes estimated he was among the country’s wealthiest people and worth $29.8 billion.

During the course of his last three decades, he was involved in struggles with unions over the building of his casinos and then with those investigating the manner by which he acquired the right to build in notoriously corrupt China. But attempts to bring him down by treating his business tactics as fodder for scandal failed. More important, by the 2000s, his attention had already been diverted to the causes that would consume his last years and animate so much of the coverage devoted to him: support for Israel and those politicians he hoped he could rely on to back the Jewish state.

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IN ADDITION to embodying the entrepreneurial spirit that had created so many other Jewish business success stories, Adelson also possessed the mindset of the postwar American Jew whose ethnic and religious identity revolved around the horrors of the Holocaust and support for Israel. Indeed, he was fond of recalling that on his first trip there, Adelson wore his late father’s shoes, fulfilling that poor man’s unfulfilled dream of someday visiting the Holy Land.

But it was Adelson’s 1991 marriage to Miriam Farbstein, an Israeli physician who specialized in treating victims of addiction, that focussed him on Zionist activism and politics. From that point on, the Jewish state would become a consuming interest into which he would not merely pour wealth but do so in a manner that would substantially alter the course of both Israeli and American politics.

The list of Israeli and Jewish institutions and causes to which he contributed is endless. His largesse in the form of an estimated $140 million donation enabled the Birthright project to expand to the point where it became a near-universal right of passage for young Jews. He would also become the principal funder for the Yad Vashem World Holocaust Remembrance Center and fund hospitals and schools throughout the country.

But Adelson wasn’t content to merely give. A supporter of Israel’s right-wing parties and an opponent of American pressure on the Jewish state to make concessions its people believed were dangerous to its security, he became one of the leading donors to Republican candidates as the GOP completed its transformation into a lockstep pro-Israel coalition.

Just as Adelson’s contributions to philanthropic causes were on an epic scale, with him giving hundreds of millions to various institutions, his involvement in politics was similarly grand. His donations to pro-Israel candidates and conservative Republicans were both generous and strategic. Over time, he eventually rejected the approach of AIPAC—whose most generous donor he was for years. The pro-Israel lobby has adhered to a rigorously bipartisan approach because its goal is to maintain support for the Jewish state among a broad cross-section of American officeholders. But that meant providing support for liberal Democrats who would betray the interests of the pro-Israel community on issues like their support for the dangerous Iran nuclear deal. Adelson believed in a more direct approach to politics. He backed those he considered faithful friends to the cause he cared about, and he would cut off those who weren’t. Over time, that led him to eschew the AIPAC model and give his backing to the more conservative-oriented Israel American Council.

His embrace of Republicans whom he considered sufficiently supportive of Israel was open-handed. But he was not shy about using the access that gave him to express his views about the U.S.-Israel relationship in ways that surprised some politicians.

He gave millions to help stage President George W. Bush’s second inauguration. But he then bluntly confronted Bush in a White House meeting in 2008 when he believed that Secretary of State Condoleezza Rice was wrongly pressuring Israel to make territorial concessions. Bush’s reply was equally telling when he told Adelson that he could not be more pro-Israel than its then–Prime Minister Ehud Olmert, who was eager to cut a deal with the Palestinians before he left office.

But while Adelson was prohibited from having the same impact on Israeli politics by campaign finance laws, he was still able to help his friend Benjamin Netanyahu, who would return to the prime minister’s office the following year. Adelson’s financing of Israel Hayom was widely resented in the Israel media not just because it broke the left-wing chokehold on the press, but because his willingness to absorb huge losses meant that the right-wing paper could still be broadly distributed. Though he would eventually break with Netanyahu over the prime minister’s willingness to sacrifice his relationship with Adelson in return for favors from other publishers, Adelson’s willingness to keep funding Israel Hayom remained a powerful weapon that empowered the center-right majority of the Israeli electorate to prevail over an opposition that had the aid of the rest of the press.

Adelson’s willingness to give historic amounts to candidates he preferred put him in the crosshairs of such newspapers as the Times, which accused him of trying to buy the presidency by giving up to $100 million to Newt Gingrich’s doomed 2012 Republican primary campaign. But while Adelson’s money could be effective, Gingrich’s failure also proved that no one, not even a billionaire with deep pockets, could actually buy the presidency.

Nevertheless, it was Adelson’s willingness to step in and back Donald Trump’s campaign in 2016 when most major Republican donors wanted no part of him after he secured the GOP nomination that proved especially fateful. He spent hundreds of millions on various candidates over the years, but no donation was more significant than his backing for Trump. It’s unlikely that his stepping into the breach during the 2016 general-election campaign made the difference in Trump’s victory, which had more to do with Hillary Clinton’s failures and his fellow billionaire’s populist appeal. But his support did win Adelson access, and he used it as he always had, to bluntly advocate for pro-Israel policies.

Trump’s tilt toward Israel happened for a variety of reasons, including the sentiments of the many Jews in his inner circle, the support of evangelicals, and the 45th president’s hostility to the foreign-policy establishment. But the importance of Adelson’s single-minded advocacy for the moving of the U.S. Embassy from Tel Aviv to Jerusalem, as well as other moves that benefited Israel, should not be discounted. Though credit for it does not belong to him alone, it was in no small measure a tribute to Adelson’s willingness to use his influence for what he—and most Israelis and pro-Israel American Jews—believed was the right thing. In the year before he died, Adelson purchased the property that served as the ambassador’s residence in Herzliya at a price of $67 million—a record for the sale of a private residence in that country—so as to make it even more difficult for a future president to reverse Trump’s move. Adelson spared no expense for anything that he considered to be in the best interest of the Jewish people.

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HIS SPENDING on Republicans and settlement projects—such as the funding of a medical school at Ariel University, which is located in a West Bank settlement—earned him the particular abuse of left-wing Jews and liberal pundits. In an era when most large-scale Jewish donors had adopted the mindset of most non-Orthodox Jews and were concentrating on liberal boutique causes rather than traditional Zionist ones, Adelson was the exception that proved decisive. If anti-Zionists and leftists reviled him at his death, it was primarily a sign of their resentment at the way he embodied the old paradigm of solidarity with Israel and its security that had largely gone out of fashion.

That is why Adelson’s legacy can’t entirely be measured in the amount of dollars he funneled into Jewish causes or in the number of pro-Israel candidates he helped elect. At a time when Jewish institutions in the United States were imperiled by demographic change, he stepped in to fund programs such as Birthright to help keep a shrinking community alive. In politics, his devotion to the concept that Israel should be allowed to decide its own fate rather than be dictated to by the United States paid off in measures that allowed that concept to prevail.

In the end, like the wealthy Jews who had interceded for their communities in perilous times in the past, Adelson had the courage of his convictions. In the 21st century, that made him unpopular with those who despised the conservatives he backed, the role money played in politics, the use of donations to promote Israel, and even the impact of American philanthropy on Israeli society. But more than any other member of his generation, Sheldon Adelson was true to the obligations that Judaism places on both the uses of wealth and on the requirement for solidarity with other Jews. Though lacking the style and grace of many of the grandees, the great thinkers and leaders of the past, Sheldon Adelson has earned an honored place in the annals of Jewish history.

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