Over the past decade, Jared Kushner’s family company has spent billions of dollars buying real estate. His personal stock investments have soared. His net worth has quintupled to almost $324 million. And yet, for several years running, Mr. Kushner — President Trump’s son-in-law and a senior White House adviser — appears to have paid almost no federal income taxes, according to confidential financial documents reviewed by The New York Times.

Even after they ascended to top White House positions, Ivanka Trump and Jared Kushner continued to benefit from an extraordinary number of  investment deals carried out by the companies they once ran, ethics  filings released Monday evening showed.

Joshua Harris, a founder of Apollo Global Management, was advising Trump administration officials on infrastructure policy. During that period,  he met on multiple occasions with Jared Kushner, President Trump’s son-in-law and senior adviser, said three people familiar with the meetings. Among other things, the two men discussed a possible White House job for Mr. Harris. The  job never materialized, but in November, Apollo lent $184 million to  Mr. Kushner’s family real estate firm, Kushner Companies.

Last May, Jared Kushner accompanied President Trump, his father-in-law, on the pair’s first diplomatic trip to Israel, part of Mr. Kushner’s White House assignment to achieve peace in the Middle East. Shortly before, his family real estate company received a roughly $30 million investment from Menora Mivtachim, an insurer that is one of Israel’s largest financial institutions, according to a Menora executive.

Even hours after the Senate vote, tax experts were scratching their heads over precisely what had made it into the final version of the bill and the impact of some significant  provisions. Still, it was clear that many changes expanded tax benefits for the wealthiest taxpayers, while other attempts to close loopholes fell by the wayside. The bill would add $1 trillion to deficits over the coming decade.

President Trump’s son-in-law, a top adviser, had help building a real estate empire from a member of one of Israel’s wealthiest families the Raz Steinmetz. Raz's uncle, and the family’s most prominent figure, is the billionaire Beny Steinmetz, who is under scrutiny by law enforcement authorities in four countries. In the United States, federal prosecutors are investigating whether representatives of his firm bribed government officials in Guinea to secure a multibillion dollar mining concession. In Israel, Mr. Steinmetz was detained in December and questioned in a bribery and money laundering investigation. In Switzerland and Guinea, prosecutors have conducted similar inquiries.