NEW YORK — Early last year, a private equity billionaire started paying regular visits to the White House.

Joshua Harris, a founder of Apollo Global Management, was advising the Trump administration on infrastructure policy. 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 Harris.

The job never materialized, but in November, Apollo lent $184 million to Kushner’s family real estate firm, Kushner Cos., to refinance the mortgage on a Chicago skyscraper.

It was triple the size of the average property loan made by Apollo’s real estate lending arm, securities filings show. And it was one of the largest loans Kushner Cos. received last year.

An even larger loan came from Citigroup, which lent the firm and one of its partners $325 million to help finance a group of office buildings in Brooklyn. That loan was made in spring 2017, soon after Kushner met in the White House with Citigroup’s CEO, Michael L. Corbat, according to people briefed on the meeting. The two men talked about financial and trade policy and did not discuss Kushner’s family business, one person said.

There is little precedent for a top White House official meeting with executives of companies as they contemplate sizable loans to his business, say government ethics experts.

“This is exactly why senior government officials, for as long back as I have any experience, don’t maintain any active outside business interests,’’ said Don Fox, acting director of the Office of Government Ethics in the Obama administration. “The appearance of conflicts of interest is simply too great.’’

The White House referred questions to Kushner’s lawyer, Abbe Lowell, who did not dispute the meetings between Kushner and the executives took place. Peter Mirijanian, a spokesman for Lowell, said in a statement that Kushner “has met with hundreds of business people.’’ He said Kushner “has taken no part of any business, loans or projects with or for’’ Kushner Cos. since joining the White House and has followed ethics advice.

Kushner’s White House tenure has been dogged by questions about conflicts of interest between his government work and family business. He steers US policy in the Middle East, for example, but his family company continues to do deals with Israeli investors.

Kushner recently lost his top-secret security clearance amid worries from some US officials that foreign governments might try to gain influence with the White House by doing business with Kushner. And investigators for the special counsel looking into Russian interference in the 2016 election have asked questions about Kushner’s interactions with potential overseas investors, said a person familiar with the matter.

Kushner resigned as CEO of Kushner Cos. when he joined the White House, and he sold a small portion of his stake in the company to a trust controlled by his mother. But he retained the vast majority of his interest in Kushner Cos.