By turning to one of his most prominent attorneys over the last two decades for representation in the investigation into possible collusion with Russia during the 2016 election, President Donald Trump is seemingly inviting more criticism, seasoned Washington insiders say.

Marc Kasowitz, the aggressive New York “uberlitigator” known for his “attack dog” style, has represented Trump’s interests in numerous cases. He represented Trump during his Atlantic City casino bankruptcies, he sued a former New York Times reporter for $5 billion in libel damages for allegedly under-reporting Trump’s net worth – the judge dismissed the case because Trump “failed to establish malice” – and he defended Trump University from allegations of fraud, a case in which Trump ultimately agreed to settle.

“The fact that he has been Trump’s lawyer for years will not be a plus,” said one prominent Washington attorney who personally knows special counsel and former FBI director Robert Mueller. “This pick will strike Mueller as strange.”

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Kasowitz also represents former Fox News anchor Bill O’Reilly, and has represented celebrities like Robert DeNiro.

Trump has called Kasowitz and his former partner in the firm, David Friedman, “phenomenal lawyers.” They’ve already had an outsized impact on his administration. Friedman is now U.S. Ambassador to Israel. The White House removed former Sen. Joe Lieberman from consideration for FBI director because he works for Kasowitz. Lieberman had been Trump’s top pick to replace former FBI Director James Comey.

The media has heaped praise on Kasowitz for his work in the private sector. One report described him as “the toughest lawyer on Wall Street.” And while Trump is still said to be rounding out his legal team, the outsider approach is raising eyebrows with D.C. attorneys who have defended presidents during special investigations before.

“Maybe Trump is going to bring somebody else in,” said prominent Washington attorney Robert Bennett, “because you have to hire somebody who has worked in the Bermuda Triangle of Congress, the Justice Department and the media. What you do in one part of it can effect another part of it.”

Bennett, who represented former President Bill Clinton during the special counsel investigation of the Monica Lewinsky scandal in the late 90s that ultimately led to Clinton’s impeachment, said the job is not for civil lawyers who don’t have vast political experience in Capitol Hill and the White House.

“Unless he brings in somebody with that kind of experience,” he said, “I think it’s a very dangerous situation for the president.”

The Washington attorneys who spoke to Fox News say Trump has a penchant for leaning on combative attorneys, such as Roy Cohn who represented Trump in the 70s. Cohn was quoted as saying: “I bring out the worst in my enemies, and that’s how I get them to defeat themselves.”

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A D.C. attorney who requested anonymity said there is a difference between a tough lawyer and a confrontational one.

“If you go back into Trump’s history, you can see Roy Cohn had a real influence,” the lawyer said. “He was a real pr**k. That’s not going to go over well with Mueller. The government has all the cards or most of the cards. While you don’t roll over and play dead, you can’t use the butcher’s ax, either.”

Kasowitz himself has faced media criticism for his ties to Russia. His firm represents OJSC Sberbank, Russia’s largest bank, accused in U.S. federal court of conspiring with granite company executives and others to raid the assets of a competitor. Sberbank is majority-owned by the Russian government.

Sberbank reportedly had ties to other prominent American political figures such as Tony Podesta, the Democratic super-lobbyist and brother of Democratic strategist John Podesta.

Bennett said Kasowitz representing Sberbank isn’t necessarily controversial, but it could look bad, given the insatiable media narrative of questionably cozy ties to the Kremlin.

“I don’t see that as a big deal. Although, with all the focus on Russia I don’t know why you’d pick a guy with a relation to Russia,” Bennett said.

Meanwhile, the order to appoint a special counsel issued by Deputy Attorney General Rod Rosenstein also opens up the possibility to scrutinize issues outside the 2016 election, such as President Trump’s conversation about intelligence on ISIS with Russian officials in the Oval Office on May 10th. For that, Washington insiders say, you need an attorney with national security expertise.

“If Mr. Kasowitz is unfamiliar with intelligence information or with the President's Constitutional authorities in national security,” said Robert Eatinger, former acting General Counsel of the Central Intelligence Agency and founder of SpyLaw Consulting. “I'm certain he can retain an expert to assist him in the special counsel investigation should it include the president's reported disclosure of highly classified intelligence information with Russian Foreign Minister Sergei Lavrov and Ambassador Sergey Kislyak.”

All in all, don’t be confrontational with Mueller, said Bennett.

“If it’s a close call” at the end of the investigation and Mueller is on the fence with what to do with the evidence, Bennett said, “at the end of the day you want somebody who will listen to you.”