President Trump’s lawyer told attorneys representing Paul Manafort and Michael Flynn last year that the president might be willing to pardon his former aides if they faced criminal charges stemming from an investigation into Russia’s election interference, according to three people familiar with the discussions.

The president’s lead lawyer at the time, John Dowd, was described as floating the idea of a pardon for Manafort, Trump’s former campaign chairman, and Flynn, the former national security adviser, at a vulnerable moment for the two men. Both Flynn and Manafort had contacts with Russians while advising Trump and were under investigation by Special Counsel Robert Mueller’s team, but neither had been charged at that point.

Mueller indicted Manafort on charges of tax fraud and money laundering in late October. Flynn pleaded guilty in December to lying to investigators and agreed to cooperate with the Mueller probe.

Dowd insisted Wednesday that he did not raise the idea of pardons with lawyers representing the two men.

“I had no such discussions with them,” Dowd said in a phone interview. “We never talked about pardons. There was no reason to talk about pardons. No, ma’am.”

A spokesman, Jason Maloni, and a former lawyer, Reginald Brown, for Manafort declined to comment. Robert Kelner, an attorney for Flynn, also declined to comment. The outreach from Dowd was first reported by the New York Times.

The allegation that Dowd offered two key witnesses in the Russia investigation a legal safety net comes amid Mueller’s increasing focus on whether the president obstructed justice by seeking to blunt or shut down the inquiry.

Legal experts said prosecutors could view floating the idea of a presidential pardon to people under investigation as a criminal effort to obstruct justice. Raising such a possibility could be considered an incentive for witnesses not to cooperate with investigators.

“I’ve only been asked about pardons by the press, and have routinely responded on the record that no pardons are under discussion or under consideration at the White House,” Ty Cobb, the White House lawyer working on the Russia investigation, said in a statement.

Trump, however, did express a keen interest last spring and summer in his power to pardon, according to people familiar with the situation. While interviewing lawyers as possible candidates to represent him in the probe, aides said, Trump asked his team whether he could pardon his advisers, his family members and even himself.

One person familiar with the outreach to Manafort’s team said Dowd over the summer relayed to the former campaign chief’s lawyers that a pardon was a possibility. A person familiar with the Flynn discussions said Dowd called Kelner sometime last year to tell him Trump believed there was no merit to the case against Flynn and the “president would consider a pardon.”

White House aides and Trump’s legal advisers privately expressed concern Wednesday about the situation and said Dowd may have mentioned pardons off the cuff and failed to recognize the intense sensitivity of the subject at that moment.

“I hope he didn’t do it,” said one Trump aide. “It would be just awful – a terrible end to his good career.”

What specifically Dowd offered – and whether Trump approved the idea – could now become part of Mueller’s investigation of Russian interference with the 2016 election and whether there was any coordination with the Trump campaign. His inquiry has focused on several potential pillars of obstruction, including Trump’s decision to fire FBI Director James Comey in May 2017 and his campaign to pressure Attorney General Jeff Sessions to quit. Trump was angry that Sessions had recused himself from the probe, which led to the appointment of a special counsel, and hoped a new attorney general would remove the need for Mueller.

Legal experts are split about whether the president can commit obstruction of justice while exercising powers that are constitutionally afforded to him, such as the pardon power.

“It’s an open question about which there’s been a great deal of debate,” said Paul Rosenzweig, a lawyer who served on the team of Independent Counsel Ken Starr that investigated President Clinton.

But, he added, “given the openness of both the legal and factual questions, it would be irresponsible of Mueller not to add this to his inquiry.”

“The full truth is that it’s stone-cold stupidity on his part if he actually did it,” Rosenzweig added.

The possibility of a pardon raises new questions about why Manafort has repeatedly refused to cooperate with Mueller’s team. He faces a raft of serious felony charges and, if convicted, faces decades in prison. Manafort has pleaded not guilty and has told associates he believes he can win in court.

Manafort has been under intense pressure from the special counsel’s office.

In July, FBI agents raided his condominium in Alexandria, Virginia, rousting Manafort and his wife from bed with a search a warrant – a tactic rarely employed in white-collar criminal cases. Mueller’s prosecutors also required one of Manafort’s lawyers to testify before the grand jury, also a step rarely taken. And they have now indicted him on money laundering, conspiracy, and bank and tax fraud charges related to political consulting work he conducted in Ukraine before joining Trump’s campaign.

On Tuesday, prosecutors filed new documents in court revealing that the FBI has assessed that a longtime Manafort business associate had ties to Russian intelligence during the 2016 campaign. The documents did not name the associate, but the description offered by prosecutors matched Konstantin Kilimnik, a Russian national who had worked as Manafort’s translator and office manager in Kiev.

Manafort has acknowledged having extensive contact with Kilimnik during the five months he served as Trump’s campaign chairman in 2016, including holding two in-person meetings with him. Emails that have been read to The Washington Post also show that Manafort asked Kilimnik to offer “private briefings” about the campaign to Oleg Deripaska, a Russian business magnate who is close to the Kremlin. Deripaska’s spokeswoman has said he was never offered such briefings.

The new information underscores why Mueller has been so focused on obtaining Manafort’s cooperation. Manafort’s deputy, Rick Gates, who was also in contact with Kilimnik while working for Trump, has already agreed to plead guilty.

Flynn’s family and advocates have indicated publicly that they are hoping Trump will pardon Flynn.

Just after Christmas, Joseph Flynn tweeted at the president to urge him to pardon his brother Michael.

“About time you pardoned General Flynn who has taken the biggest fall for all of you given the illegitimacy of this confessed crime in the wake of all this corruption,” he wrote.

Joseph Flynn deleted the tweet and later issued a new one with a more collegial tone: “Mr. President, I personally believe that a pardon is due to General Flynn, given the apparent and obvious illegitimacy of the manner in which the so called ‘crimes’ he plead guilty to were extracted from him. I ask for quick action on this. Thank you and keep up the good work!”

In December, after Flynn pleaded guilty, Trump was asked by reporters if he would be willing to pardon Flynn, and Trump replied he wasn’t ready to discuss it – “yet.”

“We’ll see what happens,” he told reporters before a speech he was giving at the FBI’s National Academy. “Let’s see, I can say this: When you look at what’s gone on with the FBI and the Justice Department, people are very, very angry.”