Donald Trump’s top lawyer John Dowd (pictured) suggested pardons for former advisors Michael Flynn and Paul Manafort over the Russia inquiry.

Dowd raised the possibility in discussions last year, said three people with knowledge of the discussions. They took place before Manafort was indicted in October over money laundering, over his business with pro-Russian entities in Ukraine, and Flynn pleaded guilty in December to lying to investigators over his contacts with Russian Ambassador Sergey Kislyak.

The timing raises issues over possible obstruction of justice in the inquiry of Special Counsel Robert Mueller. Analysts say a pardon offer could be seen as trying to block any cooperation of Manafort and Flynn with the investigation.

Flynn is cooperating with Mueller’s team, but Manafort is holding out and pledging to fight in court.

Dowd’s conversation with Flynn’s lawyer Robert Kelner took place sometime after Dowd took over last summer as Trump’s personal lawyer. Dowd also spoke with Manafort’s attorney Reginald Brown.yer.

It is unclear whether Dowd discussed the pardons with Trump before his conversations with Kelner and Brown.

Dowd, who resigned last week as Trump’s attorney, issued a denial on Wednesday: “There were no discussions. Period. As far as I know, no discussions.”

Another Trump lawyer, Jay Sekulow, and White House lawyer Ty Cobb said they have never discussed pardons. However, “two people briefed on the interviews” said current and former administration officials have told Mueller’s team of conversations with Trump about potential pardons.

In one meeting last year with lawyers from the White House Counsel’s office, Trump asked about the extent of his pardon power. In other meetings with senior advisors, Trump raised the prospect of pardoning Flynn.