Trump’s history with Jeanine Pirro

Dimitrios Kambouris/Getty Images

Donald Trump first became acquainted with the Pirros over 30 years ago when he hired Albert Pirro to serve as a real estate lawyer. At the time, Jeanine Pirro was serving as a Westchester County Court judge, and the couple ran in the same New York City social scene as Trump. Trump remained friends with Judge Pirro over the intervening decades, and long before his own political ambitions, Pirro ran for the Republican senate nomination to oppose Hilary Clinton in 2005. She dropped out of the race, but Trump showed his friendship and support by donating to her campaign at the time, and when she ran the next year to oppose Andrew Cuomo for the New York attorney general seat, he donated to that campaign as well (via Vanity Fair). 

She gave up her ambitions of pursuing political office for a TV career, landing a headlining role in CW’s reality courtroom show Judge Jeanine Pirro, which was canceled in 2011 just before Pirro signed on with Fox. And in 2016, she wrote a book called Liars, Leakers, and Liberals: The Case Against the Anti-Trump Conspiracy, which The Washington Post called “the most gushing” of the “sycophantic” books that had come out at the time about the then-new president. Throughout his presidency, Pirro took the president’s side and made sometimes-controversial assertions that landed her in hot water even with her network, but nothing deterred her loyalty and her drive to express it on her show (via Vanity Fair).

The Truth About Judge Jeanine Pirro And Donald Trump’s Relationship

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By Elizabeth S. Mitchell/Jan. 22, 2021 1:05 pm EST

Trump’s history with Jeanine Pirro

Dimitrios Kambouris/Getty Images

Donald Trump first became acquainted with the Pirros over 30 years ago when he hired Albert Pirro to serve as a real estate lawyer. At the time, Jeanine Pirro was serving as a Westchester County Court judge, and the couple ran in the same New York City social scene as Trump. Trump remained friends with Judge Pirro over the intervening decades, and long before his own political ambitions, Pirro ran for the Republican senate nomination to oppose Hilary Clinton in 2005. She dropped out of the race, but Trump showed his friendship and support by donating to her campaign at the time, and when she ran the next year to oppose Andrew Cuomo for the New York attorney general seat, he donated to that campaign as well (via Vanity Fair). 

She gave up her ambitions of pursuing political office for a TV career, landing a headlining role in CW’s reality courtroom show Judge Jeanine Pirro, which was canceled in 2011 just before Pirro signed on with Fox. And in 2016, she wrote a book called Liars, Leakers, and Liberals: The Case Against the Anti-Trump Conspiracy, which The Washington Post called “the most gushing” of the “sycophantic” books that had come out at the time about the then-new president. Throughout his presidency, Pirro took the president’s side and made sometimes-controversial assertions that landed her in hot water even with her network, but nothing deterred her loyalty and her drive to express it on her show (via Vanity Fair).

She gave up her ambitions of pursuing political office for a TV career, landing a headlining role in CW’s reality courtroom show Judge Jeanine Pirro, which was canceled in 2011 just before Pirro signed on with Fox. And in 2016, she wrote a book called Liars, Leakers, and Liberals: The Case Against the Anti-Trump Conspiracy, which The Washington Post called “the most gushing” of the “sycophantic” books that had come out at the time about the then-new president. Throughout his presidency, Pirro took the president’s side and made sometimes-controversial assertions that landed her in hot water even with her network, but nothing deterred her loyalty and her drive to express it on her show (via Vanity Fair).