Why Trump Takes Legal Advice From Fox’s Conspiracy-Stoking ‘Judge Jeanine’

Derick Dirmaier

Sean Hannity may be perceived as Fox News’ most unabashed cheerleader for President Donald Trump, but Jeanine Pirro is giving him a run for his money.

“There is a cleansing needed in our FBI and our Department of Justice,” the former judge said in a remarkable opening monologue on last Saturday’s installment of her weekly Fox show “Justice With Judge Jeanine.” “It needs to be cleansed of individuals who should not just be fired but who need to be taken out in handcuffs.”

Pirro then ran through a list of intelligence officials who should be imprisoned for what she framed as a politically-motivated offensive to “destroy Trump”: former FBI Director James Comey, Deputy FBI Director Andrew McCabe, former Deputy Assistant FBI Director Peter Strzok, former Associate Deputy Attorney General Bruce Ohr, and Special Counsel Robert Mueller.

This might just seem like particularly outlandish rhetoric from a pundit known for arguing that the sight of Muslims carrying boxes into their own homes should prompt calls to law enforcement, and urging police officers to turn their backs on “anti-Trump, leftist, socialist, cop-hating” New York Mayor Bill DeBlasio.

But Pirro’s words carry more currency with Trump than your average Fox host’s. The pair have been friends for some two decades, and the President continues to solicit Pirro’s legal advice. Last month, as the New York Times reported, Pirro sat down in the Oval Office with Trump and senior administration officials to try to goad him into appointing a special counsel to investigate a uranium deal involving Russia, approved while Hillary Clinton was secretary of state.

“She’s one of those people who calls him ‘Donald,’” former Trump campaign adviser Michael Caputo told TPM. “There are very few. She counsels him upon request. I mean, the President calls her.”

The two are bonded by their roots in the insular, tough-talking New York GOP political world; years of interfamilial professional and personal ties; stridently pro-police attitudes; interactions with the legal system that never quite landed them in trouble; and an innate understanding of how to keep the cameras on them—at any cost. For both the pundit and the President, politics is just good business.

“The President considers Jeanine a friend,” White House deputy press secretary Lindsay Walters told TPM in response to a request for comment.

Before TPM reached out to Fox News for comment for this story, a network spokesperson called unprompted to ask about the nature of the upcoming story on Pirro and offer assistance. The network did not respond to a detailed list of questions provided by TPM on Thursday.

The ties between the pair date back to the early 1990s, when Pirro was a rising star in the Westchester County GOP and Trump was a real estate mogul trying to maintain his flashy image despite a string of bankruptcies.

Trump retained Pirro’s then-husband Albert, a politically-connected land use attorney, to assist him with several projects in Westchester. Al Pirro also served as a “lawyer-lobbyist for Trump” as he sought to stop New York from legalizing casino gambling to preserve his Atlantic City cash cows, Trump Taj Mahal and Trump Plaza, according to a veteran political operative and acquaintance of Jeanine Pirro’s who requested anonymity to discuss her friendship with Trump candidly.

“So Al had this business relationship with Trump over numerous years,” the operative said. “Simultaneously, they all hung out together in Palm Beach” where the Pirros had a house and Trump’s Mar-a-Lago estate is located.

The families grew close. A 1999 New York Magazine profile quotes Trump calling Al Pirro “incredibly intelligent and effective” and Jeanine “sexy as hell.” One anecdote from the profile describes Trump’s daughters, Ivanka and Tiffany, wandering the lawn at a 500-person Mexican-themed cookout at the Pirros’ Hudson, New York home, where an attendee said Jeanine was wearing “high heels, dancing the Macarena.”

At the time, she was in the midst of a soaring career trajectory. After starting as a Westchester County assistant district attorney in 1975, she was elected in 1990 as the county’s first female judge, and to three successive terms, beginning in 1993 and ending in 2005, as the county’s first female DA.

Frank Nicolai, a retired judge in the county whose time on the bench coincided with Pirro’s, remembered her to TPM as a “very hardworking judge, certainly knowledgeable about criminal law.”

“She was known at that time as somebody who was really interested in victim’s rights,” said Peter Leavitt, a retired Westchester county judge, noting that Pirro emphasized prosecuting cases involving domestic violence against women and children.

But Leavitt criticized the frequent TV hits Pirro would do to promote those cases, saying that “everything with Jeanine at that time was self-aggrandizement.”

Bennett Gershman, a Pace University law professor who has tracked Pirro’s career for years, called her “probably the most political prosecutor I’ve ever encountered.”

“She wanted to create a star moment for herself as a stepping stone for higher office,” said Gershman, who once filed a misconduct complaint against Pirro for discussing the H.I.V. status of an indicted sex offender during a press conference.

Her attempted star turn came in 2005-06 when she dropped out of the New York Senate race against Hillary Clinton (after receiving donations from the likes of Trump) and became the GOP nominee for state attorney general, losing by nearly 20 points to Andrew Cuomo. Her bids for statewide office were dogged by her husband’s legal troubles (Al Pirro was convicted in 2000 of hiding over $1 million in personal income on falsified returns, some of which his wife also signed) and her own. In 2006, Pirro came under federal investigation for asking former NYC police commissioner Bernie Kerik how best to secretly record her husband, whom she believed was cheating on her. No charges were ultimately filed, and the Pirros split up the following year.

Like Trump, Pirro ultimately found a home on TV, where their brash, say-anything personalities were assets. Trump spun “The Apprentice” into a hit franchise, while Pirro won a daytime Emmy for a reality court show, “Judge Jeanine Pirro,” before landing at Fox News in 2011. Trump was a frequent guest on the network.

When Trump announced his 2016 presidential run, Pirro became an early, ardent supporter. She advised #NeverTrump Republicans to “get in line” with the GOP frontrunner’s unorthodox campaign. According to Caputo, she would stop by Trump Tower for occasional meetings with Trump, “talking strategy and bucking him up.” The Access Hollywood recording in which Trump boasted of sexually assaulting women was “disgusting, devastating and embarrassing,” she told viewers, but she “still, without a doubt” would vote for him.

This unyielding loyalty paid off. Trump in March urged the public to watch an episode of “Judge Jeanine” in which Pirro said House Speaker Paul Ryan (R-WI) should step down for embarrassing the President by failing to pass Obamacare repeal. He filmed an episode of her show in the Oval Office in May, and the New York Times reported he rarely misses an episode of the 9 p.m. ET Saturday program.

Trump supporters are Pirro viewers, and vice versa. The longtime political operative friendly with the Fox host told TPM this symbiotic relationship sometimes means promoting narratives that might not be fully grounded in reality, but appeal to the converted.

“I think she realized that the Trump message works for her viewership and she’s feeding her viewership and it’s good for her ’cause it keeps her numbers up,” the source said. “And she’s a personal supporter of Trump ’cause she’s known him for so long.”

“That’s something the President never forgets,” Caputo said of Pirro’s allegiance. “She may have been stern with him about something she disagreed with, but she never left his column of support. Those are the people the President relies on most because they’ve never given up on him.”

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