Igor Fruman, an associate of Rudy Giuliani, pleaded guilty on Friday to solicitation of a contribution by a foreign national. He could receive a sentence of up to five years.

The federal charge stems from a case accusing Fruman, 56, of funneling foreign money to US campaign coffers.

These aren’t the first charges Fruman faced. He and Lev Parnas, another Giuliani associate, were indicted in October 2019 for conspiracy to violate the ban on foreign donations to federal and state elections, making false statements, and falsifying records to the Federal Election Commission. Both men, who were close with Giuliani when he was former President Trump’s lawyer, pled not guilty.

On Friday, when Fruman entered his guilty plea, he told the judge he was in contact with a potential investor who was a foreign national. He sent the individual a list of possible donations to politicians in states legalizing marijuana — as Fruman was trying to launch a cannabis business.

“I deeply regret my actions and apologize to the court,” Fruman said.

His sentencing is set for January 21.

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Giuliani associate Igor Fruman pleads guilty to solicitation of a contribution by a foreign national