Alan Dershowitz, the retired Harvard law professor, had an adorable 6-foot-tall stuffed bear in his daughter’s bedroom and a potential legal problem on his hands.

It was the early 1990s, and his client, hotel magnate Leona Helmsley, had gifted him the stuffed animal upon the birth of his baby girl. But Helmsley later admitted that she had stolen the bear from Donald Trump, keeping it when she sold him Rumplemayer’s, a now shuttered New York ice cream parlor famous for its stuffed bear collection — which was part of the deal.


Viewing himself as a paragon of ethical conduct, Dershowitz told her he no longer felt comfortable keeping the gift. Helmsley said she didn’t want the bear back and waved him off, telling him to take his problem to Trump.

“I called him and I said, ‘Mr. Trump, I have a bear that belongs to you,’” Dershowitz said in an interview on Wednesday. “He laughed and said, ‘I know Leona stole it. We have the inventory. Tell your daughter it’s from Donald.’”

Almost three decades later, their friendly acquaintance has taken center stage as Trump’s mounting legal problems threaten to engulf his administration.

On Tuesday evening, Dershowitz dined at the White House with the president, who has been considering firing special counsel Robert Mueller or deputy attorney general Rod Rosenstein in the wake of an FBI raid on the New York home and office of his longtime lawyer Michael Cohen.

Dershowitz said that he was there to talk about the Middle East with the president and his senior advisers. “It was a previously scheduled meeting,” he told POLITICO.

He was back at the White House on Wednesday, huddling again with senior Trump aides.

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The role of Trump legal ally is a surprising turn for the lifelong Democrat — that is, if you haven’t been watching Fox News for the past year. Dershowitz has become one of the president’s most reliable TV defenders, routinely attacking the legal grounds for Mueller’s investigation into Russian interference in the 2016 election, and defending Trump’s right to fire former FBI Director James Comey.

Before the president’s legal problems became personal, Dershowitz was hitting the airwaves to defend the constitutionality, if not the morality, of his travel ban.

Dershowitz is also a civil libertarian and skeptic of prosecutorial power. Last year, he published “Trumped Up: How Criminalization of Political Differences Endangers Democracy.”

On Wednesday, he told “Meet the Press” host Chuck Todd that he believes deputy attorney general Rod Rosenstein, who oversees the Mueller probe, should recuse himself from the investigation.

But Dershowitz has made clear he doesn’t want to officially join the president’s legal team: At age 79, he has said, he wants his freedom to act according to the same credo that drove him to call Trump about a purloined gift 30 years ago.

But the president, who has followed Dershowitz’s legal commentary on television and cheered him on in real-time on Twitter, has increasingly turned to him privately as his stable of lawyers has dwindled. He has spoken with him about a range of issues, including his escalating legal troubles, people familiar with the conversations said. Top White House advisers said they view Dershowitz as an important legal asset, even if he’s not officially on the payroll.

Trump’s growing relationship with one of his most outspoken legal defenders reflects more than the president’s habit of soliciting advice from the last person he talked to, or anyone he perceives as an ally on television. Over the past month, the president has lost one of his personal attorneys, John Dowd, and has been unable to replace him: Several high-profile attorneys — including former George W. Bush lawyer Ted Olson and former U.S. Attorney Dan Webb — publicly declined to join his defense.

Dershowitz told POLITICO on Tuesday evening after the dinner that there had been no change to his relationship with the president and that he remains nothing more than an independent outside commentator. He has also made clear that he does not offer legal advice to the president off-screen. “Look, I don’t give advice to the president, except on television,” he told Fox News’ Sean Hannity on Monday.

But the president’s desire to rely more on Dershowitz underscores how desperately he is seeking the informal legal advice of attorneys outside his shrinking legal team.

Trump’s freewheeling conversations about the Mueller probe have become a source of concern for his lawyers, who have warned him not to discuss the investigation with anybody but his own counsel. And Dershowitz isn’t the only one Trump is soliciting advice from, sources said. The president has been asking for legal advice, one person familiar with the conversations said, from virtually any attorney who calls him up, even after being warned of the danger he is putting himself in.

The president has continued to discuss the case with longtime attorney Marc Kasowitz, who originally led his legal team but stepped down last summer, as well as with Fox News host Jeanine Pirro, a former Westchester County prosecutor and longtime Trump friend.

“Trump should not be having any conversations about [the investigation] with anyone who is not official representing him,” said a person familiar with the case.

But that didn’t stop Trump from wanting time Tuesday night with Dershowitz — a man he respects for his Harvard Law credentials and enjoys as a familiar name from the older, easier days in New York.

Over the years, Dershowitz has spent time with Trump at Mar-a-Lago, as a guest of New England Patriots owner and Trump pal Robert Kraft, as well as at the White House on multiple occasions.

His legal commentary first came onto Trump’s radar last year when he defended the constitutionality of Trump’s rewritten travel ban — his advisers even at one point pulled the president aside backstage at a rally to show him clips of Dershowitz on television defending him.

As the president’s legal woes have grown more personal, Dershowitz’s commentary has kept up. Earlier this week, he argued that the FBI’s raid on Trump attorney Michael Cohen may have violated lawyer-client privilege, and he called on civil libertarians to defend the president. “Many civil libertarians have remained silent about potential violations of President Trump’s rights because they strongly disapprove of him and his policies. That is a serious mistake, because these violations establish precedents that lie around like loaded guns capable of being aimed at other targets,” he wrote in The Hill.

Over the past several months, the president has seized on Dershowitz’s public remarks, using them as intellectual justification for his own views.

“So stated by Harvard Law Professor Alan Dershowitz,” Trump tweeted last month after quoting him at length.

“Special Council is told to find crimes, whether a crime exists or not. I was opposed to the selection of Mueller to be Special Council. I am still opposed to it. I think President Trump was right when he said there never should have been a Special Council appointed because there was no probable cause for believing that there was any crime, collusion or otherwise, or obstruction of justice!,” Trump wrote, misspelling “special counsel” as he quoted from a Dershowitz appearance on Fox News.

If their politics sometimes differ, Trump and Dershowitz are kindred spirits when it comes to working the media for maximum exposure.

For weeks leading up to Tuesday’s dinner, Dershowitz appeared to be playing a coy game with journalists who asked him whether he had been approached by the president, or anyone in his inner circle, about joining the legal team, refusing to confirm or deny those rumors. “You know that no lawyer could ever comment about whether he has been asked,” he told NBC News’ Chuck Todd earlier this month.

In a second interview on Wednesday, however, Dershowitz categorically denied that Trump had personally asked him to join his legal defense team.

Instead, he has used the newfound fame that alights on anyone in Trump’s orbit to tout his Middle East bona fides and position himself as a conduit to Israeli Prime Minister Benjamin Netanyahu. Recalling his run-in with Trump at Mar-a-Lago six months ago, he said the president’s main concern was Israel, not the law.

“He pulled me aside,” Dershowitz recalled, “and said, I have messages for you to give to Bibi.”

Darren Samuelsohn and Josh Gerstein contributed to this report.

