Legal experts are confounded by Michael Cohen's revamped strategy

Brendan McDermid/Reuters

Michael Cohen.

• President Donald Trump's longtime lawyer Michael Cohen has revamped his legal strategy.
• Cohen is making it seem as if he will turn on his old boss.
• Experts are confounded by the strategy.

There has been a dramatic shift in President Donald Trump's former longtime lawyer Michael Cohen's legal strategy, and experts are confounded by what exactly is the aim of his latest maneuvering.

Cohen has gone from virtual silence to suddenly sounding as if he is ready to turn on the president at a moment's notice. Gone are the days when Cohen sought to appear as close to Trump as possible; now he's saying in an interview with ABC's George Stephanopoulos that his family "and this country" have his "first loyalty."

Soon, Cohen will split with his existing legal team at McDermott Will & Emery and will have his defense guided by Guy Petrillo, a partner at Petrillo Klein & Boxer who has extensive experience in the Southern District of New York and is the kind of lawyer a person would choose if he or she were seeking to cut a deal with prosecutors, experts told Business Insider. Cohen has also brought on Lanny Davis, notable for his work as a lawyer and spokesperson for former President Bill Clinton during the Monica Lewinsky scandal.

Cohen, who worked for Trump over the past decade, is under investigation for possible campaign-finance violations, bank fraud, wire fraud, illegal lobbying, and other crimes. The FBI raided his home, office, and hotel room in April, seizing roughly 4 million documents.

In distancing himself from Trump, Cohen has criticized the "zero-tolerance" immigration policy, hinted through his friends that he might cooperate with the government and provide information about the president, and caused a dizzying news cycle after being photographed with Tom Arnold, an outspoken anti-Trump comedian.

'Cohen's shown such awful judgment on every front that it's hard to read what he's doing and why'

The entire strategy has left experts puzzled.

"Cohen's shown such awful judgment on every front that it's hard to read what he's doing and why, because you can't attribute smart maneuvering to him," Ken White, a criminal defense attorney, told Business Insider, adding, however, that he believes hiring Petrillo and Davis "shows an uptick in" Cohen "not being a total idiot."

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Donald Trump.

Davis's hire, however, has befuddled others. A former federal prosecutor, who requested anonymity to speak candidly on the matter, said Davis's hiring was puzzling.

"Ordinarily, a federal prosecutor does not want potential cooperators to do anything to create publicity," the former federal prosecutor said. "At this point, Lanny Davis is in the business of legal crisis PR, not providing nuts-and-bolts legal advice."

The person listed a few possibilities for what Cohen could be doing.

"It is possible that Michael Cohen hired Lanny Davis solely to push Donald Trump's buttons," they said. "It is possible that Michael Cohen is doing things that are counterproductive to his eventually being accepted as a cooperator. It is also possible that Michael Cohen has been bluffing to try to get Donald Trump and the Trump Organization to pay his legal bills, so that he can afford to continue an active defense."

The strategy has opened the door to renewed speculation that Cohen might not have much information to offer the government on Trump. Maybe he's bluffing in hopes of a pardon or, as the former federal prosecutor said, to have Trump pay his legal bills.

During this stretch, Trump has distanced himself from Cohen as well, suggesting that the investigation has far more to do with Cohen's business dealings than anything Cohen did for the president. Rudy Giuliani, Trump's personal attorney, has repeatedly assured that nothing in the Cohen investigation will prove damaging to the president.

But Cohen has intricate knowledge of the $130,000 hush money payment made to porn star Stormy Daniels (real name Stephanie Clifford) prior to the 2016 presidential election in exchange for her silence over the allegation that she had a 2006 affair with Trump - something Trump denies. He was involved in a similar arrangement with former Playboy model Karen McDougal, who also alleged an affair with Trump. And Cohen had a central role in the failed Trump Tower Moscow project, a venture that was in the works during the presidential campaign.

"We can't be sure yet either way whether he has damaging stuff about the president (that is, more damaging than the president of the United States reimbursing his fixer for paying hush money to a porn star, which apparently we're cool with as a baseline)," White said. "The media glare and the distorting impact of presidential politics makes this one very hard to analyze."

Sources close to Cohen are signaling that he has something damaging on Trump - but others aren't so sure

As Cohen has changed up his strategy, sources close to him have seemingly been tripping over each other in signaling to the press that Cohen does have damaging information and will soon reveal it.

Some told CNN on Monday that Cohen has a strong parallel to John Dean, former White House counsel to President Richard Nixon who testified against the president during the Watergate proceedings. The same sources told the outlet that Cohen had a message for Giuliani and Trump: "The truth is not you or your client's friend."

Meanwhile, the strategy has been met with some level of condemnation from both Giuliani and Michael Avenatti, Daniels's attorney. After Davis attacked Giuliani on Twitter on Monday and suggested that followers "stay tuned," hinting at Cohen bombshells, both Giuliani and Avenatti fired back, albeit for different reasons.

In a text message exchange with Business Insider, Giuliani hit Davis for his past work for Clinton and said he didn't "get" why Cohen would hire "a flak caught lying in the past as a 'lawyer'?????"

Avenatti took issued with Davis hinting at there being more to come from Cohen.

"Stay tuned?" Avenatti tweeted. "This isn't some game or opp to tease for a reality show. This is serious business. If Cohen has info, he needs to share it NOW with the American people. He can't standby while more damage is done & then later claim he's a hero because he cut a plea to save himself."

Cohen shouldn't appear so eager to cut a deal

If Cohen does indeed have nothing to offer prosecutors, Renato Mariotti, a former federal prosecutor and partner at Thompson Coburn, told Business Insider that Trump's fixer "has made a mistake by appearing so eager to cut a deal."

"He is not going to get a deal unless he can provide substantial assistance to prosecutors," Mariotti said. "Cohen's recent actions don't make much sense. Even if he has something important to offer, he should not appear so eager to get a deal, and shouldn't be saying so much in public."

The only way Cohen's recent maneuvering does make sense, Mariotti said, is if Cohen is angling "for a pardon and doesn't believe that a private message from his lawyer could get through to Trump."

He continued: "It's more likely that Cohen is just making another foolish move."