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Giuliani’s Lady Friend Pushed Trump to Give Him Presidential Medal of Freedom

Giuliani’s business partner and companion, Maria Ryan, reportedly asked Trump to award the former New York City mayor the medal.

Rudy Giuliani’s close female companion led the bizarre push to award the disbarred lawyer the highest honor in the country.

Maria Ryan, 59—who has denied being Giuliani’s girlfriend—wrote to then-President Trump during his first term, urging him to award the Presidential Medal of Freedom to the 81-year-old ex-New York City mayor, according to Giuliani biographer Andrew Kirtzman.

The letter was reportedly intercepted by Bernard Kerik, who was working as Giuliani’s adviser at the time, the New York Times reported.

Ryan finally got her wish after Trump announced Sunday on Truth Social that he would consider Giuliani for the medal, which is regarded as the highest honor in the country.

Ryan, a nurse practitioner and former hospital administrator in New Hampshire, accompanied Giuliani, 81, to a minor league baseball game in New Hampshire hours before he was involved in a car accident Saturday evening that left him with a fractured vertebra, per WMUR.

Giuliani later praised Ryan for overseeing his medical care. “Thank you to @MariaRyanNH who is a board certified nurse practitioner overseeing the care of America’s Mayor . (Nurse practitioners do everything a doctor does except surgery)" he wrote.

Ryan has been one of Giuliani’s biggest champions and closest confidants of late. After Joe Biden won the election in 2020, Ryan sent an email to the Trump campaign requesting that Giuliani be paid $20,000 per day in compensation for his contributions, as Giuliani admitted in 2021.

Giuliani defended Trump in multiple lawsuits and stoked debunked conspiracies about election fraud. Giuliani unsuccessfully attempted to declare bankruptcy, and in 2024, he was disbarred as a lawyer in New York and Washington D.C. for his defamatory claims about election fraud.

Dating rumors between Giuliani and Ryan were fueled after the release of recordings of Giuliani discussing the nature of their relationship. The tapes were submitted to a court after a former employee of Giuliani’s filed a sexual harassment suit against him in 2023. “She loves me. But she can’t leave her family, including her husband,” he reportedly said. Both Ryan and Giuliani have vehemently denied the allegations that they were ever romantically involved.

The Daily Beast has reached out to a representative for Giuliani and Ryan for comment.

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Amber LevisBreaking News Intern

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