President Donald Trump's former lead defense lawyer, John Dowd, last year raised the prospect that Trump would pardon Michael Flynn and Paul Manafort, The New York Times reported Wednesday.

Flynn, the former national security adviser, pleaded guilty in December to lying to federal investigators. Meanwhile, Manafort, the former Trump campaign chairman, has pleaded not guilty to dozens of charges against him as part of the special counsel Robert Mueller's Russia investigation.

Legal experts say that if Dowd did broach the subject of pardons for both men, it may have been improper but most likely would not constitute obstruction of justice.

John Dowd, the former lead defense attorney in charge of managing President Donald Trump's communications with the special counsel Robert Mueller, suggested the possibility of pardons for two of the most critical figures in the Russia investigation at the height of the inquiry, The New York Times reported Wednesday.

Citing three people with knowledge of the discussions, The Times reported that Dowd last year spoke to lawyers representing Michael Flynn, the former national security adviser, and Paul Manafort, the former Trump campaign chairman, as Mueller's investigation was closing in on both men.

Flynn pleaded guilty in December to one count of lying to federal investigators about his contacts with Russians and is now believed to be cooperating with Mueller. Manafort has pleaded not guilty to several charges.

According to The Times, Dowd broached the subject of a possible pardon with Flynn's lawyer, Robert Kelner, last summer, and with Manafort's, Reginald Brown at the time, shortly before Manafort's indictment in October.

Manafort has since been charged with dozens of other financial crimes; most of the charges relate to his pro-Russia lobbying work in Ukraine.

Dowd resigned from representing Trump last week.

Michael Flynn. Chip Somodevilla/Getty Images

Flynn and Manafort were closely tied to Trump in the White House and during the campaign, respectively.

The president has long said publicly and privately that he believes the case against his former national security adviser is thin and that Flynn was unjustly targeted in what Trump has characterized as a politically motivated "witch hunt."

Trump fired Flynn in February 2017. The White House initially said it was because he misled Vice President Mike Pence about conversations he had during the presidential transition period in 2016 with Sergey Kislyak, then Russia's ambassador to the US. But on December 2, one day after Flynn's guilty plea was announced, Trump tweeted that he had to fire Flynn because he "lied to the Vice President and the FBI."

James Comey, the former FBI director, testified last year that Trump had asked him multiple times to drop the bureau's investigation into Flynn. Legal experts said that if Trump knew Flynn had misled investigators when he asked that of Comey, as his December tweet appeared to indicate, it would significantly bolster the obstruction-of-justice case Mueller has been building against the president since last year.

Dowd later claimed responsibility for the tweet.

Meanwhile, Manafort's status as Trump's campaign chairman in 2016 is also likely to be of interest to investigators, as he was spearheading the campaign at several pivotal moments in the race, including:

The campaign's move to gut an amendment to the GOP platform that called for increased US aid to Ukraine.

Top campaign operatives' meeting with two Russian lobbyists offering dirt on the 2016 Democratic presidential nominee, Hillary Clinton.

A breach of the Democratic National Committee that is widely believed to have been carried out by Russian hackers.

Dowd, Trump's defense attorney Jay Sekulow, and the White House lawyer Ty Cobb all told The Times that there had been no discussions of possible pardons for Manafort and Flynn at any point during the investigation.

Dowd did not respond to an additional request for comment.

In response to reporters' questions about the Times report, the White House press secretary, Sarah Huckabee Sanders, pointed back to Cobb's statement, adding, "There is no discussion or consideration of this at that at this time."

Inappropriate, but not illegal?

Legal experts said that if such a discussion did occur, it would not be appropriate, but it may not rise to the level of obstruction of justice.

"The president's power to pardon is absolute and not subject to review even if he does it for political reasons," said Jeffrey Cramer, a former federal prosecutor who spent 12 years at the Department of Justice.

"A president pardoning defendants if they don't plead guilty — and 'cooperate' is the unspoken word here — would be a new use of the pardon power," he said.

Dowd's reported message to the defendants "puts us, yet again, in uncharted waters," Cramer added. "Dangling a pardon if they keep their mouths shut would certainly be of interest to Mueller. Nobody can say it is criminal. Only a partisan hack would argue it's proper."

Andrew Wright, an associate in the White House counsel's office under President Barack Obama, highlighted that Dowd, Cobb, and Sekulow had all denied that Dowd broached the possibility of pardons for Flynn or Manafort.

"I hope they're right," he said. "Floating the possibility of a pardon to a witness considering cooperation with a grand-jury investigation would be bad if Dowd represented another nonpresidential witness."

Wright added, however, that Dowd represented Trump in his personal capacity, as opposed to Cobb, who represents the White House.

"Last time I checked, the pardon power is official, not personal," Wright said. "That kind of act could twist up not only the client, but also the lawyer, in a criminal obstruction probe."