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The Trump family's web of business and political interests is coming under intense scrutiny, with the spotlight firmly on Jared Kushner, President Donald Trump's son-in-law and White House senior adviser.
Apollo's $184 million loan in November was aimed at refinancing the mortgage on a Chicago skyscraper, while Citigroup's $325 million amount in the spring of 2017 was directed at financing office buildings in Brooklyn, the Times said.
Kushner met with Apollo founder Joshua Harris in the White House multiple times last year and even discussed the possibility of a White House job for Harris, sources told the newspaper.
An Apollo spokesman told CNBC that Harris wasn't involved in the company's decision to extend the Chicago loan, adding that the matter went through the firm's standard approval process.
Ethics experts have long frowned on the idea of senior administration officials with active corporate activities because of potential conflicts of interests.
A spokesman for Kushner's lawyer told the Times that he "has taken no part of any business, loans or projects with or for" Kushner Companies since joining the White House.
Still, the Times' report is the latest in a series of worrying claims about the Trump family profiting from the presidency, which has sparked concern both inside and outside the White House.
Kushner's relations with foreign government officials is a key reason why he's been unable to obtain permanent security clearance, the Washington Post reported on Tuesday. The 37 year-old's top-secret government security clearance was recently downgraded.
His business dealings also make him prone to manipulation by foreign governments, the Post added, noting that officials in at least four countries had privately discussed how to benefit from Kushner's lack of government experience.
Special counsel Robert Mueller's team, who is looking into Russian meddling in the 2016 U.S. election, have asked questions about Kushner's interactions with potential foreign investors, the Times said.
The White House did not respond to CNBC's request for comment.
Citigroup provided this statement to CNBC:
"The loan we closed last March was to a joint venture of which Kushner Companies is a less than 50% partner. While Kushner Companies has been a Citi client for years, we dealt exclusively with RFR Realty, the other partner in the joint venture, on this loan. Our CEO was not involved in the transaction and never discussed it with Jared Kushner."