Paul Manafort, the second of Donald Trump’s presidential campaign managers, is in serious legal jeopardy. The Washington Post reported on Wednesday that during his five-month control of the Trump campaign, Manafort offered a Kremlin-linked Russian oligarch multiple “private briefings” on the status of the U.S. election.

Less than two weeks before Trump clinched the GOP nomination, Manafort wrote an email to an intermediary of aluminum magnate Oleg Deripaska to ask if the Basic Element founder would like to be regularly updated on the progress of the campaign.

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“If he needs private briefings we can accommodate,” Manafort wrote on July 7, 2016. Deripaska is reportedly among the 2-3 oligarchs Russian President Vladimir Putin turns to on a regular basis.

Little more than a year later, Manafort’s Virginia residence was raided by the FBI in the predawn hours. CNN reported earlier this week that the FBI also secured a secretive order from the Foreign Intelligence Surveillance Act (FISA) court to wiretap Manafort's phone in Trump Tower both during and after the election.

In another email shortly after his appointment as Trump’s second campaign manager, the Post reported, Manafort asked, “How do we use to get whole?” While the Post reports that the "notes appear to be written in deliberately vague terms," several emails were sent after Manafort attended a Trump Tower meeting with Donald Trump Jr. to entertain a Russian offer to help the Trump campaign.

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Perhaps even more puzzling than a seasoned political operative’s decision to offer campaign secrets to a close ally of Putin in writing is the excuse provided to the Post by Manafort’s spokesperson.

“It’s no secret Mr. Manafort was owed money by past clients,” Jason Maloni said, dismissing the email exchanges as an “innocuous” effort to collect past debts.

But in a 2015 court complaint filed in Virginia, Deripaska claimed Manafort owed him $19 million related to a failed investment in a Ukrainian cable television business. Both Manafort and Deripaska have confirmed that the Russian businessman paid Manafort as an investment consultant. Manafort was a lobbyist for Ukrainian President Viktor Yanukovych through early 2014, and has long been a big investor in the former Soviet republic.

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Manafort used his Trump campaign email account to correspond with a Ukranian associate who has previously been reported to have suspected ties to Russian intelligence, Politico reported Wednesday. His emails have been turned over to special counsel Robert Mueller and congressional investigators. Manafort, who has been the subject of an FBI investigation for three years, has denied ever "knowingly" communicating with Russian intelligence operatives during the election.