This pattern does not necessarily indicate any illegal behavior. But experts told WNYC that if someone was trying to launder money, this would be a typical way to do it, turning ill-gotten gains into legitimate cash by moving it through the various transactions. Once the mortgage was taken out, the money would be “clean” for the individual, with the property as collateral and the original source and purchaser forgotten. Manafort denied any wrongdoing and said it was common to buy real estate with limited liability companies, as he did.

Despite the large cash flows, Manafort found himself in danger of foreclosure on a townhouse in Brooklyn and properties in California, The Wall Street Journal reports. He was saved by a $16 million bailout, spread between November and January, from a bank owned by a Trump adviser. Manafort has received other loans from Trump friends before, highlighting the closeness of his ties to Trump. Nonetheless, the White House has argued of late that Manafort was a mere short-term volunteer for the campaign.

Manafort was also investigated for money laundering on Cyprus, NBC News reports. The island is a common outlet for money from Russia. Starting in 2007, Manafort opened at least 15 bank accounts and incorporated at least 10 companies. The large amounts of money flowing into Manafort’s Cypriot assets, including from Deripaska, raised concerns about money laundering at the bank, which opened an investigation. Manafort then closed his accounts there. NBC reports that the manner in which the accounts were being used was curious:

Banking sources said that in October 2009, one of the 15 Manafort-associated bank accounts in Cyprus received a payment of a million dollars and left the account on the same day. Experts said the way the multiple accounts and companies were used suggests they were set up to deliberately make it difficult for auditors to track the movement of funds.

The vast amounts of cash accord with what is known about Manafort’s work. According to the AP scoop, he was to receive $10 million annually from Deripaska. In 2016, The New York Times reported that documents turned up in Ukraine showed that Manafort was to receive almost $13 million in off-the-books cash payments from the political party of Viktor Yanukovych, the Kremlin client for whom Manafort worked as a consigliere. Yanukovych was deposed during a revolution in 2014.

Deripaska and Manafort eventually ended up at legal odds over a business transaction for a telecom company that ran through the Cayman Islands.

Manafort has always cut a somewhat sinister figure: He is fond of dark suits with wide pinstripes, giving him an old New York gangster look, and he has worked for a variety of unsavory clients—not just Yanukovych and reportedly Putin, but also Ferdinand Marco and Mobutu Sese Seko. Yet simply appearing sinister and actually breaking the law are two rather different matters.