Why Michael Flynn is now trying a 'high risk' legal strategy as his sentencing approaches

With a sentencing date approaching and a judge presiding over his case who has demonstrated open antipathy toward him, Michael Flynn could be expected to keep his head down and create as few waves as possible.

Instead, the former national security adviser is taking another approach.

House Intelligence Committee Chair Adam Schiff (D-CA) revealed Monday that Flynn is failing to satisfactorily cooperate in his investigation of Russian interference in the 2016 election and its ties to the president and his campaign. Schiff cited Flynn's lawyer, the pugnacious Sydney Powell, as a key problem in negotiations between committee staffers and Flynn's team, saying she has shown "a troubling degree of unprofessionalism."

“Notwithstanding repeated efforts by committee staff to engage with your counsel and accommodate your adjournment requests, you have, to date, failed to comply with the committee’s subpoena or cooperate with the committee’s efforts to secure your compliance," Schiff wrote in a letter to the former national security adviser.

Schiff explained that he sought Flynn's testimony in July, but his team delayed scheduling it. Now, he's demanding that Flynn appear Sept. 25 for a hearing before the committee.

CNN legal analyst Renato Mariotti noted that Flynn and his team are carrying out a "high risk strategy" by antagonizing the committee chair.

In particular, he argued that Flynn's lawyers' assertion that he will plead the Fifth Amendment to any question other than inquiries about his name is untenable.

"A witness can only take the Fifth as to specific questions if the answer to that question would be incriminating," Mariotti said. "What that means is that the answer would have to help the government convict you of a crime. So you can't take the Fifth if you're asked about the weather or the clothes you wore yesterday unless those facts are relevant to potential criminal charges against you."

He added: "In addition, you can't plead the Fifth in relation to crimes that you've already been convicted of. So once Flynn was sentenced, he could not plead the Fifth as to questions relating to the lies that he told the FBI because he already would be convicted and sentenced."

Flynn has already said he was guilty of lying to the FBI about his contacts with the Russian ambassador during Trump's presidential transition, though there have been some suggestions that his new legal team may seek to withdraw that plea — a perilous gambit.

Mariotti argued that though the committee could likely force Flynn to testify through the courts eventually, his real danger lies in his upcoming sentencing before Judge Emmet Sullivan this fall. While Special Counsel Robert Mueller, who originally brought the case against Flynn, only recommended a maximum six-month sentence for his crimes, Sullivan has the latitude to decide on a significantly longer term than that. And Sullivan has already shown his willingness to buck the prosecutors' calls for leniency and his personal disgust at Flynn's actions when he urged the defense to forestall sentencing back in December.

“Arguably, you sold your country out," Sullivan told Flynn last year.

And while Flynn may not technically be violating his cooperation agreement in his new behavior toward the Intel Committee, the judge may read into his actions a lack of remorse for his crime.

"The judge is required by law to take into account all of the 'history and characteristics' of Flynn, and that will include whether his cooperation (or lack thereof) with Congress," Mariotti wrote on Twitter. "Flynn got a *really* favorable deal from Mueller, agreeing to plead only to a single count of lying to the FBI, which carried with it a recommended sentence of 0 to 6 months in prison (which could be served via probation or home detention). But he could get up to five years."

Since Flynn shook up his legal team and hired Powell — known to be openly hostile to the Russia investigation — many have suspected that he may be aiming for a pardon rather than a short sentence. Assuming that, his actions are much easier to explain. Nothing he is doing right now appears geared at shortening his sentence. Instead, it will likely lengthen it. But a presidential pardon would make that peril evaporate, and many of Flynn's actions — stonewalling Schiff, attacking the Justice Department —that aren't likely to please Sullivan will be looked upon favorably by Trump.

There may even be something of a shoot-the-moon strategy in play. Flynn may think that by goading Sullivan into giving him a harsher sentence, he is more likely to earn a full pardon from Trump.

Whether Trump will actually go through with a pardon is an open question. There's reason to think he'd be inclined to do so, out of spite and a sense of his own personal vindication and power, but issuing the pardon might trigger a serious backlash. And if someone is counting on Trump's loyalty to save them, they probably haven't been paying close attention the last four years.