On September 4, 2025, former President Donald Trump announced that Rudy Giuliani, once hailed as "America's Mayor" for his leadership of New York City after the September 11, 2001 attacks, will be awarded the Presidential Medal of Freedom. The announcement, made via Trump’s Truth Social platform, immediately sparked debate across the political spectrum, given Giuliani’s recent legal and professional troubles—including disbarment, criminal charges, and a high-profile defamation judgment.
Trump’s statement was characteristically emphatic, calling Giuliani "the greatest Mayor in the history of New York City, and an equally great American Patriot." He added, "As President of the United States of America, I am pleased to announce that Rudy Giuliani... will receive THE PRESIDENTIAL MEDAL OF FREEDOM. Details as to time and place to follow." According to The New York Times, this decision comes just days after Giuliani was hospitalized following a car crash in New Hampshire. His security chief, Michael Ragusa, reported that Giuliani suffered a fractured thoracic vertebra, multiple lacerations, contusions, and injuries to his left arm and leg, but was expected to be released from the hospital soon.
The Presidential Medal of Freedom, established in 1963 by President John F. Kennedy, is the highest civilian honor in the United States. It is awarded to individuals "who have made exceptional contributions to the security or national interests of America, to world peace, or to cultural or other significant public or private endeavors," according to the White House. Previous recipients include luminaries like Martin Luther King Jr., Rosa Parks, and Mother Teresa. Yet, Trump’s selection of Giuliani for this honor has raised eyebrows, especially in light of Giuliani’s recent legal woes.
Giuliani’s career has been marked by both extraordinary achievement and dramatic controversy. Serving as New York City mayor from 1994 to 2001, he was widely praised for his leadership in the aftermath of the September 11 attacks, earning national and even international recognition. He later mounted a brief campaign for the Republican presidential nomination and became a familiar figure in American politics.
However, Giuliani’s more recent years have been fraught with legal and reputational challenges. As Trump’s personal lawyer and a key architect of efforts to overturn the 2020 presidential election, Giuliani advanced claims of widespread fraud that were repeatedly rejected by courts. According to Brooklyn Eagle, Giuliani’s actions led to his disbarment in both New York and Washington, D.C., for making false statements about the election. He was also criminally charged in Georgia and Arizona in connection with attempts to reverse Trump’s loss to Joe Biden.
One of the most significant legal blows to Giuliani came in the form of a civil defamation case brought by two Georgia election workers, Ruby Freeman and Wandrea “Shaye” Moss. The women alleged that Giuliani’s promotion of false claims about the 2020 election not only damaged their reputation but also led to threats and harassment that made them fear for their lives. As reported by Brooklyn Eagle and other outlets, the court awarded the two women nearly $150 million in damages—a sum that Giuliani reportedly delayed paying, further compounding the controversy. In a letter to the editor published on September 4, 2025, one reader remarked, “He ruined the lives of two women,” highlighting the emotional and personal toll the case took on the victims.
Despite these setbacks, Trump’s decision to bestow the nation’s highest civilian honor on Giuliani is consistent with his pattern of using the award to recognize political allies. During his first term, Trump awarded the Medal of Freedom to figures such as GOP donor Miriam Adelson, late Supreme Court Justice Antonin Scalia, right-wing radio host Rush Limbaugh, and Representative Jim Jordan (R-Ohio). The move has prompted comparisons to those previous honorees—some of whom, like Giuliani, were celebrated in certain circles and deeply polarizing in others.
Giuliani’s supporters argue that his leadership during the September 11 crisis and his decades of public service merit the recognition. They point to his transformation of New York City’s crime rate and his role in uniting the city during its darkest hours. Trump himself wrote that Giuliani is “an equally great American Patriot,” doubling down on this narrative of heroism and public sacrifice.
Critics, however, see the award as an attempt to rewrite recent history and rehabilitate Giuliani’s tarnished legacy. They note that the Medal of Freedom is traditionally reserved for those whose contributions are unambiguously positive and far-reaching, and argue that Giuliani’s recent actions—particularly his role in the 2020 election aftermath—disqualify him from such an honor. As one letter writer put it, “Why shouldn’t a convicted felon give the highest civilian award in the United States to a guy like this?” The sarcasm in the remark underscores the skepticism with which many are viewing Trump’s decision.
The controversy is not just about Giuliani’s personal conduct but also about the broader meaning and integrity of the Presidential Medal of Freedom. For many, the award symbolizes the nation’s gratitude for service and sacrifice; for others, its value is diminished when given to figures embroiled in legal and ethical scandals. The debate over Giuliani’s worthiness reflects deeper divisions in American politics, particularly over the legacy of the Trump administration and the ongoing fallout from the 2020 election.
Meanwhile, Giuliani’s own health and legal situation remain in flux. Following the car accident in New Hampshire, he was hospitalized with serious injuries but, according to reports, was expected to make a full recovery. His criminal cases in Georgia and Arizona are ongoing, and the financial consequences of the defamation judgment continue to loom large.
For Giuliani, the Medal of Freedom represents a dramatic twist in a career already defined by highs and lows. For Trump, it is another opportunity to reward loyalty and challenge the mainstream narrative about his closest allies. For the nation, it is a reminder of how the symbols and rituals of American public life can become battlegrounds in the struggle over truth, justice, and memory.
As the details of the award ceremony remain to be announced, the debate over Giuliani’s legacy—and the meaning of the Medal of Freedom itself—shows no sign of abating. The story of Rudy Giuliani, once a symbol of unity and now a lightning rod for controversy, continues to unfold in the public eye.
