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When former Trump national security adviser Michael Flynn stands before a federal judge on Tuesday to receive his sentence after pleading guilty to lying to federal agents about his telephone contacts with the Russian ambassador, one unanswered question will loom over the courtroom.

Why did he lie?

As a retired lieutenant general in the US Army, a decorated military intelligence officer with 33 years of service to his country, and a former director of the Defense Intelligence Agency, General Flynn well knew that any telephone contacts with Russia鈥檚 ambassador in Washington would likely be recorded 鈥� and perhaps monitored 鈥� by US intelligence officials.

He also knew that he could be prosecuted for making false statements to federal agents.

Nonetheless, when two FBI counterintelligence agents showed up at the White House on Jan. 24, 2017 鈥� four days into the new Trump administration 鈥� Flynn was less than fully truthful.聽

Nearly two weeks earlier, a Washington Post columnist had quoted 鈥渁 senior government official鈥� as saying that Flynn had had repeated telephone contacts with Russian Ambassador Sergey Kislyak on the same day that then-President Barack Obama announced an escalation of US sanctions against Russia in retaliation for Russia鈥檚 interference in the 2016 presidential election.

The Logan Act prohibits private individuals from engaging in policy negotiations with foreign countries. But it has never been enforced.

The agents wanted to talk to Flynn about his contacts with Russia during the final month of the Obama administration. Flynn agreed to talk.

What Flynn didn鈥檛 know is that the two agents had already reviewed transcripts of the conversations he had with Mr. Kislyak, according to court documents, and were testing Flynn to see how much he would reveal, and whether he would be truthful.聽

鈥淚f Flynn said he did not remember something [the agents] knew he said, they would use the exact words Flynn used ... to try to refresh his recollection,鈥� a recently released FBI memo says. 鈥淚f Flynn still would not confirm what he said ... they would not confront him or talk him through it.鈥�

Following the interview, there were at least two areas of concern: In response to whether he had asked Russia to use its power on the United Nations Security Council to delay or defeat a resolution critical of Israeli settlements, Flynn claimed this was not discussed. It was.

And when the agents asked whether Flynn had asked Russia not to retaliate against the US after Mr. Obama imposed new sanctions, Flynn falsely claimed that this, too, was not discussed.

Flynn did more than just lie to the agents. He also deceived Vice President Mike Pence, chief of staff Reince Preibus, and White House spokesman Sean Spicer.聽

Relying on Flynn鈥檚 assurances, the vice president repeated Flynn鈥檚 untruthful account of his contacts with Kislyak in a television interview.

When Flynn鈥檚 story started to crumble in the days that followed, it was his deception of Pence that was cited as grounds for his removal. By Feb. 13, Flynn was gone, having served only 24 days as national security adviser.

Still, the question remains: why did Flynn lie?

Legal analysts are divided over possible explanations.

鈥淲hen people lie, there is always a motive,鈥� says Gene Rossi, a former federal prosecutor who is now a defense lawyer in Washington. 鈥淭he key issue for me is: Was he instructed to lie to the media and other people, including the FBI? Was he instructed to do that?鈥�

It is clear from documents filed in court by special counsel Robert Mueller that Flynn was not working alone in his outreach to Kislyak. After each communication with the Russian, Flynn reported back to senior officials on Trump鈥檚 presidential transition team. Those officials have not yet been publicly identified.

Flynn might have lied to protect those on the transition team, analysts say. In addition, he might also have lied to protect President Trump.聽

鈥淒id Donald Trump or some other person in the president鈥檚 transition team orbit direct Flynn to [lie]?鈥� asks Andrew Wright, a research scholar at New York University and a founding editor of the 鈥淛ust Security鈥� website. 鈥淚 just don鈥檛 know.鈥�

Mr. Wright says there isn鈥檛 enough public information yet about the full scope of Flynn鈥檚 cooperation with the special counsel鈥檚 office to identify a motive.聽

鈥淚 want to see what the government has, in terms of their understanding of what motivated [Flynn] to lie 鈥� whether it was purely personal or whether it was protective of others,鈥� says Wright, a former lawyer in the White House counsel鈥檚 office during the Obama administration.聽聽

Repeated contacts with the Russians

The Mueller team has pieced together an account detailing Flynn鈥檚 contacts with the Russians.

On Dec. 21, 2016, Egypt submitted a resolution to the UN Security Council condemning Israeli settlements. Rather than veto the measure, which had long been US practice, the Obama administration decided this time to abstain 鈥� likely allowing the measure to pass.

Officials in the incoming Trump administration strongly disagreed with the decision. At the direction of a 鈥渧ery senior member of the presidential transition team,鈥� Flynn reached out to several countries in an attempt to delay or defeat the resolution, according to court documents.

Russia was among the countries he contacted, asking Kislyak on Dec. 22 if Russia would be willing to delay or veto the resolution. The following day, Kislyak essentially told Flynn no. The resolution eventually passed.

Flynn鈥檚 second interaction with Kislyak came five days later, after Obama imposed new sanctions on Russia in retaliation for its meddling in the 2016 election.

That day, Dec. 28, Kislyak reached out to Flynn, according to court documents.

The next day, Flynn contacted a 鈥渟enior official鈥� on the presidential transition team to discuss what he should tell the Russian ambassador. Immediately after that call, Flynn telephoned Kislyak and requested that Russia not escalate the situation. After relaying that message, Flynn called the senior official back to report on the substance of his conversation with the ambassador.

The following day, Dec. 30, Russian President Vladimir Putin announced that Russia would not retaliate for the new US sanctions. A day later, Kislyak called Flynn and told him that in response to Flynn鈥檚 request, Russia would not retaliate, according to court documents.

After he received the call, Flynn contacted 鈥渟enior members of the presidential transition team鈥� to relay the substance of Kislyak鈥檚 message, these documents say.

The account strongly suggests that Flynn was not reaching out to the Russians on his own.聽And they were a clear attempt to engage in diplomatic discussions with Russia at a time when Obama was still the president.

A grand conspiracy?

Although disclosures in court filings have聽added important details to the public聽understanding of the Flynn-Kislyak contacts,聽there is no evidence at this point that Trump had knowledge of or played a role in the聽episode.

That hasn鈥檛 stopped some analysts from聽suggesting a grand conspiracy involving a聽presidentially-directed coverup.

Others suggest a less explosive motive behind聽Flynn鈥檚 deception.

鈥淭he best explanation is usually the simplest one,鈥� says Paul Rosenzweig, a senior fellow at the R Street Institute who served as a lawyer on the staff of special prosecutor Ken Starr.聽 鈥淎nd if the choice is between a grand conspiracy theory and that the guy is a fool, bet on the fool.鈥�

Mr. Rosenzweig says he believes Flynn was embarrassed that his secret contacts with Kislyak were being exposed. What most likely got him into trouble, he says, was Flynn鈥檚 arrogance, and an overabundant self-confidence that he could deceive the agents and get away with it.

According to an FBI investigative memo made public last Friday, the two agents who conducted the Flynn interview 鈥渂oth had the impression at the time that Flynn was not lying or did not think he was lying.鈥�

That FBI memo, called a 302, is dated Aug. 22, 2017. Most 302s are drafted within a week or two of the investigative interview, and there is no explanation by prosecutors as to why this 302 is dated seven months after Flynn鈥檚 interview.

The 302 was released last week after Flynn鈥檚 lawyers accused prosecutors in a court filing of treating him unfairly during the Jan. 24 interview.

Prosecutors dispute the allegation. 鈥淣othing about the way the interview was arranged or conducted caused the defendant to make false statements to the FBI,鈥� senior assistant special counsel Brandon Van Grack wrote in a reply memo. 鈥淸Flynn] does not need to be warned it is a crime to lie to federal agents.鈥�

Some legal analysts agree the agents appear to have sought to entrap Flynn, citing comments made by former FBI Director James Comey at New York City鈥檚 92^nd Street Y. Mr. Comey, an outspoken Trump critic, told the audience that he personally decided to send the two agents to the White House to interview Flynn 鈥� and that he decided to bypass normal protocol.

鈥淚f the FBI wanted to send agents into the White House itself to interview a senior official, you would [normally] work through the White House counsel and there would be discussions and approvals,鈥� Comey said. 鈥淚 thought, it鈥檚 early enough, let鈥檚 just send a couple guys over.鈥澛�

Flynn鈥檚 lawyers complain in their filing that their client had been given no warning that he was a target of their investigation.

But others say they see no impropriety in how Flynn was treated.

The FBI agents appear to have followed 鈥済ood interviewing techniques,鈥� says Rosenzweig, adding that the notion of subjects being tricked or trapped into lying is largely a myth.

鈥淭he best way to avoid this problem is to not actually lie,鈥� he says. 鈥淲henever people say, 鈥業 was entrapped into lying,鈥� [I respond]: 鈥楴o, you were asked a question and you chose to lie.鈥� 鈥�

Rossi agrees. 鈥淕eneral Flynn did not need to be warned. He knew what he was doing.鈥�

Despite the seriousness of his offense, Flynn is unlikely to face a term in prison. Federal guidelines call for a sentence of zero to six months. And both the government and defense lawyers are urging US District Judge Emmet Sullivan to sentence Flynn to probation, saying Flynn provided 鈥渟ubstantial assistance鈥� to the Trump-Russia investigation. That assistance includes participating in 19 debriefing sessions with prosecutors and investigators, extending over nearly 63 hours, and assisting several ongoing investigations.

Nonetheless, it remains unclear why Flynn lied to the agents. Even the former FBI director is in the dark.

鈥淚t was clear that he was lying,鈥� Comey said in his appearance at the Y.聽鈥淏ut the why was really interesting to us. And聽I didn鈥檛 get that answer.鈥�

鈥淚 wouldn鈥檛 tell you that answer if I found it,鈥澛爃e added. 鈥淏ut I didn鈥檛 get it.鈥澛�