Apollo Global Management and Citigroup gave large loans to Jared Kushner’s family business last year after top executives from both companies reportedly had meetings at the White House.

One of Apollo’s founders, Joshua Harris, met with Kushner on multiple occasions while he was advising officials on infrastructure policy last year, the New York Times reports.

The private equity firm lent $184M to Kushner Cos. last year, which the firm used to refinance a mortgage on a Chicago skyscraper, 225 West Randolph. Kushner tried to sell the building in 2014 for $315M, seven years after it paid $275.7M for it.

The real estate company also received a $325M loan from Citigroup last spring, soon after Citigroup CEO Michael Corbat met with Kushner to discuss financial and trade policy. That loan was used to help finance the Brooklyn Dumbo Heights office complex in which Kushner owns a stake.

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

Kushner’s lawyer, Abbe Lowell, did not dispute the meetings took place, and a spokesperson for Lowell said that Kushner has met with “hundreds of business people,” and that he has taken “no part in any business, loans or projects” for Kushner Cos. during his time at the White House.

Spokespeople for Apollo and Citigroup denied that the meetings had anything to do with the loans, worth more than $500M combined. Citigroup has been a lender on deals with Kushner Cos. in the years before its former CEO was working in the White House.

“Stories like these attempt to make insinuating connections that do not exist to disparage the financial institutions and companies involved,” Kushner Cos. spokesperson Christine Taylor told the Times.

Kushner's family business has been a frequent point of ethics controversy while he has served as senior adviser to his father-in-law, President Donald Trump. His family business used his White House position to advertise a New Jersey project to potential investors in China and his dealings with lenders, including attempts to secure funding for his embattled Manhattan skyscraper, 666 Fifth Ave., have been highly scrutinized.