Getting Michael Cohen to rat out President Donald Trump may not be as simple as it sounds.

Although Trump’s detractors are rooting for Trump's personal attorney to “flip” on the president and cooperate with special counsel Robert Mueller to escape a potentially harsh prison sentence, legal obstacles make it difficult for lawyers to expose their clients’ guarded secrets.


Even if Cohen is determined to break his confidences with Trump, legal ethics might deter federal prosecutors from coaxing him to betray his professional confidences with Trump, legal veterans and experts say.

"This idea of 'flipping' Cohen — they can't just flip a lawyer to testify against a client," longtime defense attorney Harvey Silverglate said. “Even if Cohen doesn't know better, one would think the FBI and the prosecutors would know better."

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Silverglate said not only Cohen but prosecutors could be disbarred for overstepping the well-established ethical boundaries.

FBI agents raided Cohen’s home and office earlier this month and seized records and electronic devices that reportedly contain communications with Trump, whom Cohen has represented for more than a decade.

Because Cohen was Trump’s lawyer, many of those communications are likely covered by the legal principle of attorney-client privilege, which would typically prevent them from being admissible in court.

While the privilege can be waived, only Trump — and not Cohen — has the right to do so.

"It is absolutely the case that, even if he is criminally liable himself, Michael Cohen is not allowed to disclose client confidences learned through the attorney-client relationship about any client without their permission," said Paul Rosenzweig, a former legal adviser to Whitewater independent counsel Kenneth Starr.

Attorneys for Cohen and Trump declined to comment for this story. But other lawyers expect that the president's legal team would vigorously object to Cohen discussing Trump's past dealings to prosecutors. Lawyers for Trump are already fighting in court to block prosecutors' access to information the FBI seized on the grounds that it is covered by privilege.

There are exceptions to what privilege will protect. Communications made with the intent of committing or concealing a crime or fraud are exempted, for instance.

And Cohen is entitled to disclose conversations with Trump that are directly related to charges he might face.

"The ethics rules allow lawyers to disclose client confidences from a representation if the lawyer is charged with wrongdoing arising out of the representation," said New York University law professor Stephen Gillers. "You can't trade on client information unless you're charged with wrongdoing because of the representation of that client."

Lawyers said prosecutors are likely to tread carefully because any misstep could jeopardize the investigation by the U.S. attorney's office in New York into Cohen, which includes his payment of $130,000 in alleged "hush money" payment to porn star Stormy Daniels, who claims she had sex with Trump and was paid to buy her silence shortly before the 2016 election. Trump says he was unaware of the payment.

That federal probe also reportedly involves Cohen's personal business dealings, including financing of dozens of New York City taxi medallions that Cohen has owned.

Casual treatment of information from Cohen could even put at risk Mueller's investigation into alleged collusion between the Trump campaign and Russia, attorneys said. It was Mueller who uncovered and referred to New York federal prosecutors the information that triggered the raid on Cohen’s addresses.

On Saturday, Trump lashed out at press reports that Cohen might choose to "flip" against his former boss and client, but the president also seemed to emphasize that Cohen was engaged in business Trump had nothing to do with.

"Michael is a businessman for his own account/lawyer who I have always liked and respected. Most people will flip if the Government lets them out of trouble, even if it means lying or making up stories,” Trump wrote. “Sorry, I don’t see Michael doing that despite the horrible Witch Hunt and the dishonest media!”

Even if Cohen is inclined to share information about Trump with prosecutors, the government would likely want a judge to rule explicitly that the attorney-client privilege doesn't apply — either because Cohen was engaged in order to commit a crime or because the matter in question did not involve confidential legal advice.

"They have to be very careful. They don't want to taint the members of the Mueller team," said one former federal prosecutor who handled a case in which an attorney was charged criminally. "They get tainted with that, they're off this case. It's a pretty heavy penalty. ... They certainly could not simply bring [Cohen] in. They could not break that privilege without some court deciding that."

Adding to the complexity is the fact that Cohen also served as an attorney for the Trump Organization and acted on his own in various business deals. That means prosecutors could be entitled to ask some questions about Cohen's experiences in dealings with Russia, for example, but may not be entitled to pry into what Cohen told Trump on such issues or vice versa.

"They could ask about what he negotiated with the Russians but cannot ask what he told Trump or what Trump told him," said Silverglate. "The relationship between Trump and his lawyer was probably very mixed. If they were in business together and had a part of some deal together, that wouldn't surprise me."

Ultimately, divining that line will likely require a court-appointed special master to consider what is fair game for prosecutors. Any rulings on those questions could spur protracted litigation but could provide a road map for what prosecutors can talk to Cohen about and what they can't

"It's incredibly complicated. ... The special master is really essential," Silverglate added.

Veteran prosecutors says they can recall few, if any, instances in which attorneys agreed to testify freely about their clients — even in cases where attorneys have been prosecuted for alleged complicity in mafia or drug activity.

Cohen's dilemma does have at least one significant historical echo.

After President Richard Nixon's personal attorney, Herbert Kalmbach, pleaded guilty in 1974 to illegal fundraising for GOP congressional candidates, he agreed to cooperate with prosecutors to reduce his prison sentence and revealed that he knew of payments of illegal "hush money" to Watergate burglars.

Former White House counsel John Dean said Monday he does not recall attorney-client privilege being an issue because Kalmbach's activities were clearly in the fundraising and financial realm and not the provision of legal advice.

Dean, who served as White House counsel to Nixon from 1970 to 1973, said the president ultimately waived any attorney-client privilege to allow his own testimony. However, the president dropped the privilege issue only after Dean made clear he was planning to testify anyway on the ground that some of his actions amounted to crimes.

"Nixon waived the privilege, although he did know that I was going to blow right through it," said the former White House counsel, who pleaded guilty in 1973 to conspiracy to obstruct justice in connection with the payments Kalmbach made to the burglars. "I'd already flipped."

Darren Samuelsohn contributed to this report.