Late on a Thursday evening in February 2017, Japanese Prime Minister Shinzo Abe’s plane landed at Andrews Air Force Base in Maryland for his first visit with President Donald Trump. A few hours earlier, the casino magnate Sheldon Adelson’s Boeing 737, which is so large it can seat 149 people, touched down at Reagan National Airport after a flight from Las Vegas. Adelson dined that night at the White House with Trump, Jared Kushner and Secretary of State Rex Tillerson. Adelson and his wife, Miriam, were among Trump’s biggest benefactors, writing checks for $20 million in the campaign and pitching in an additional $5 million for the inaugural festivities. Adelson was in town to see the Japanese prime minister about a much greater sum of money. Japan, after years of acrimonious public debate, has legalized casinos. For more than a decade, Adelson and his company, Las Vegas Sands, have sought to build a multibillion-dollar casino resort there. He has called expanding to the country, one of the world’s last major untapped markets, the “holy grail.” Nearly every major casino company in the world is competing to secure one of a limited number of licenses to enter a market worth up to $25 billion per year. “This opportunity won’t come along again, potentially ever,” said Kahlil Philander, an academic who studies the industry. The morning after his White House dinner, Adelson attended a breakfast in Washington with Abe and a small group of American CEOs, including two others from the casino industry. Adelson and the other executives raised the casino issue with Abe, according to an attendee. Adelson had a potent ally in his quest: the new president of the United States. Following the business breakfast, Abe had a meeting with Trump before boarding Air Force One for a weekend at Mar-a-Lago. The two heads of state dined with Patriots owner Bob Kraft and golfed at Trump National Jupiter Golf Club with the South African golfer Ernie Els. During a meeting at Mar-a-Lago that weekend, Trump raised Adelson’s casino bid to Abe, according to two people briefed on the meeting. The Japanese side was surprised. “It was totally brought up out of the blue,” according to one of the people briefed on the exchange. “They were a little incredulous that he would be so brazen.” After Trump told Abe he should strongly consider Las Vegas Sands for a license, “Abe didn’t really respond, and said thank you for the information,” this person said. Trump also mentioned at least one other casino operator. Accounts differ on whether it was MGM or Wynn Resorts, then run by Trump donor and then-Republican National Committee finance chairman Steve Wynn. The Japanese newspaper Nikkei reported the president also mentioned MGM and Abe instructed an aide who was present to jot down the names of both companies. Questioned about the meeting, Abe said in remarks before the Japanese legislature in July that Trump had not passed on requests from casino companies but did not deny that the topic had come up. The president raising a top donor’s personal business interests directly with a foreign head of state would violate longstanding norms. “That should be nowhere near the agenda of senior officials,” said Brian Harding, a Japan expert at the Center for Strategic and International Studies. “U.S.-Japan relations is about the security of the Asia-Pacific, China and economic issues.” Adelson has told his shareholders to expect good news. On a recent earnings call, Adelson cited unnamed insiders as saying Sands’ efforts to win a place in the Japanese market will pay off. “The estimates by people who know, say they know, whom we believe they know, say that we're in the No. 1 pole position,” he said. After decades as a major Republican donor, Adelson is known as an ideological figure, motivated by his desire to influence U.S. policy to help Israel. “I’m a one-issue person. That issue is Israel,” he said last year. On that issue — Israel — Trump has delivered. The administration has slashed funding for aid to Palestinian refugees and scrapped the Iran nuclear deal. Attending the recent opening of the U.S. embassy in Jerusalem, Adelson seemed to almost weep with joy, according to an attendee. But his reputation as an Israel advocate has obscured a through-line in his career: He has used his political access to push his financial self-interest. Not only has Trump touted Sands’ interests in Japan, but his administration also installed an executive from the casino industry in a top position in the U.S. embassy in Tokyo. Adelson’s influence reverberates through this administration. Cabinet-level officials jump when he calls. One who displeased him was replaced. He has helped a friend’s company get a research deal with the Environmental Protection Agency. And Adelson has already received a windfall from Trump’s new tax law, which particularly favored companies like Las Vegas Sands. The company estimated the benefit of the law at $1.2 billion. Adelson’s influence is not absolute: His company’s casinos in Macau are vulnerable in Trump’s trade war with China, which controls the former Portuguese colony near Hong Kong. If the Chinese government chose to retaliate by targeting Macau, where Sands has several large properties, it could hurt Adelson’s bottom line. So far, there’s no evidence that has happened. The White House declined to comment on Adelson. The Japanese Embassy in Washington declined to comment. Sands spokesman Ron Reese declined to answer detailed questions but said in a statement: “The gaming industry has long sought the opportunity to enter the Japan market. Gaming companies have spent significant resources there on that effort and Las Vegas Sands is no exception.” Reese added: “If our company has any advantage it would be because of our significant Asian operating experience and our unique convention-based business model. Any suggestion we are favored for some other reason is not based on the reality of the process in Japan or the integrity of the officials involved in it.” With a fortune estimated at $35 billion, Adelson is the 21st-richest person in the world, according to Forbes. In August, when he celebrated his 85th birthday in Las Vegas, the party stretched over four days. Adelson covered guests’ expenses. A 92-year-old Tony Bennett and the Israeli winner of Eurovision performed for the festivities. He is slowing down physically; stricken by neuropathy, he uses a motorized scooter to get around and often stands up with the help of a bodyguard. He fell and broke three ribs while on a ferry from Macau to Hong Kong last November. Yet Adelson has spent the Trump era hustling to expand his gambling empire. With Trump occupying the White House, Adelson has found the greatest political ally he’s ever had. “I would put Adelson at the very top of the list of both access and influence in the Trump administration,” said Craig Holman of the watchdog group Public Citizen. “I’ve never seen anything like it before, and I’ve been studying money in politics for 40 years.” ***** Adelson grew up poor in Boston, the son of a cabdriver with a sixth-grade education. According to his wife, Adelson was beaten up as a kid for being Jewish. A serial entrepreneur who has started or acquired more than 50 different businesses, he had already made and lost his first fortune by the late 1960s, when he was in his mid-30s. It took him until the mid-1990s to become extraordinarily rich. In 1995, he sold the pioneering computer trade show Comdex to the Japanese conglomerate SoftBank for $800 million. He entered the gambling business in earnest when his Venetian casino resort opened in 1999 in Las Vegas. With its gondola rides on faux canals, it was inspired by his honeymoon to Venice with Miriam, who is 12 years younger than Adelson. It’s been said that Trump is a poor person’s idea of a rich person. Adelson could be thought of as Trump’s idea of a rich person. A family friend recalls Sheldon and Miriam’s two sons, who are now in college, getting picked up from school in stretch Hummer limousines and his home being so large it was stocked with Segway transporters to get around. A Las Vegas TV station found a few years ago that, amid a drought, Adelson’s palatial home a short drive from the Vegas Strip had used nearly 8 million gallons of water in a year, enough for 55 average homes. Adelson will rattle off his precise wealth based on the fluctuation of Las Vegas Sands’ share price, said his friend the New York investor Michael Steinhardt. “He’s very sensitive to his net worth,” Steinhardt said. Trump entered the casino business several years before Adelson. In the early 1990s, both eyed Eilat in southern Israel as a potential casino site. Neither built there. Adelson “didn’t have a whole lot of respect for Trump when Trump was operating casinos. He was dismissive of Trump,” recalled one former Las Vegas Sands official. In an interview in the late ’90s, Adelson lumped Trump with Wynn: “Both of these gentlemen have very big egos,” Adelson said. “Well, the world doesn't really care about their egos.” Today, in his rare public appearances, Adelson has a grandfatherly affect. He likes to refer to himself as “Self” (“I said to myself, ‘Self …’”). He makes Borscht Belt jokes about his short stature: “A friend of mine says, ‘You’re the tallest guy in the world.’ I said, ‘How do you figure that?’ He says, ‘When you stand on your wallet.’” By the early 2000s, Adelson’s Las Vegas Sands had surpassed Trump’s casino operations. While Trump was getting bogged down in Atlantic City, Adelson’s properties thrived. When Macau opened up a local gambling monopoly, Adelson bested a crowded field that included Trump to win a license. Today, Macau accounts for more than half of Las Vegas Sands’ roughly $13 bill