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Donald Trump announces Presidential Medal of Freedom for Rudy Giuliani, 9/11 hero who was hailed as ‘America’s Mayor’. Why the announcement has surprised many explained

Rudy Guiliani (left) and Donald Trump. (AP File)
President Donald Trump said on Monday he would award the Presidential Medal of Freedom to former New York Mayor Rudy Giuliani, two days after Giuliani was hospitalised following a car crash in New Hampshire.
The medal is considered the highest U.S. civilian honor and is traditionally presented to individuals who have made exemplary contributions to the prosperity, values, or security of the U.S., world peace, or other significant societal, public, or private endeavors.
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The announcement has surprised many. Here’s why.
Rudy Guiliani’s accident & what Trump said
A rental car carrying Giuliani was hit from behind at high speed on Saturday night, causing him to suffer a fractured vertebra as well as other cuts, according to a post by his spokesperson, Michael Ragusa, on social media.
Ragusa said in the post that Giuliani was “in good spirits and recovering tremendously” after the accident. He added in a later post that the crash was “not a targeted attack.”
Trump described Giuliani as “the greatest Mayor in the history of New York City, and an equally great American Patriot” in a Truth Social post on Monday announcing his decision to award him the medal. “Details as to time and place to follow,” he wrote.
@RudyGiuliani was in a car accident in NH on Aug 30 after assisting a domestic violence victim. He sustained injuries but is in good spirits and recovering tremendously. Thank you for the prayers & support. 🙏 official statement below. pic.twitter.com/ohYJCcXpjR— Michael Ragusa (@themikeragu) August 31, 2025
From 9/11 hero, America’s Mayor to failed Presidential run: Guiliani’s journey
As U.S. Attorney for the Southern District of New York, Giuliani became famous for taking on the Mafia (Five Families), Wall Street corruption (notably Ivan Boesky and Michael Milken). He built a national reputation as a tough, no-nonsense law enforcer.
He was the mayor of New York City from 1994-2001, during a time of high crime and economic anxiety. He championed “broken windows” policing and major crime reduction. Economic revitalization and Times Square redevelopment are credited to his leadership.
After the September 11 attacks, Giuliani’s calm and visible leadership earned him the nickname “America’s Mayor.” He was named Time’s Person of the Year (2001).
His fall began with a failed Presidential Run in 2008. He ran for Republican nomination.
Rudy Giuliani: The Trump supporter
Giuliani re-emerged in politics in 2016, as Trump’s top legal and political surrogate. He promoted false claims about election fraud. He led Trump’s legal efforts to overturn the 2020 election.
Acted as a political attack dog on TV, helping solidify Trump’s base support.
After Trump won, Giuliani expected to be appointed Secretary of State—but was passed over. Still, he remained loyal.
In 2018-2020, Giuliani became Trump’s personal attorney, especially during the Mueller investigation into Russian interference. Took centrestage during the Ukraine scandal, pushing for investigations into Joe Biden and his son Hunter. This directly contributed to Trump’s first impeachment in 2019.
After Trump’s 2020 loss, Giuliani led the charge to overturn the election. He filed lawsuits in multiple states, held bizarre press conferences, made false claims of widespread fraud, leading to defamation suits. Trump did not publicly distance himself, even as Giuliani’s credibility unraveled.
Giuliani’s loyalty cost him dearly. He was disbarred, indicted, and hit with massive legal penalties. He lost a $148 million defamation lawsuit to Georgia election workers he falsely accused.
Trump reportedly refused to pay Giuliani’s legal bills. Giuliani filed for bankruptcy in 2023, with tens of millions owed in legal judgments. Despite all this, Giuliani never turned against Trump. “I am more loyal than anyone he’s ever met,” Giuliani once said.
With Reuters, Agency Inputs
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The News Desk is a team of passionate editors and writers who break and analyse the most important events unfolding in India and abroad. From live updates to exclusive reports to in-depth explainers, the Desk d…Read More
The News Desk is a team of passionate editors and writers who break and analyse the most important events unfolding in India and abroad. From live updates to exclusive reports to in-depth explainers, the Desk d… Read More
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