Rudy Giuliani Bio, Age, Lawsuit, Disbarred, Wife, Daughter, 9/11, Accident

Rudolph “Rudy” William Louis Giuliani is a former American attorney and politician who served as the 107th mayor of New York City from 1994 to 2001. His political career is one of stark contrasts, marked by both widespread acclaim and severe criticism.

He is perhaps best known for his leadership during the September 11, 2001, terrorist attacks, an event that cemented his image as “America’s Mayor.” However, his later years, particularly his role as a personal attorney for President Donald Trump, have been defined by legal challenges, public scandals, and financial distress.

Early Life and Family Background

• Birth and Childhood: Born on May 28, 1944, in East Flatbush, Brooklyn, New York City, Giuliani was the only child of Helen (née D’Avanzo) and Harold Angelo Giuliani, both children of Italian immigrants.

• Family Circumstances: Raised in a Roman Catholic household, Giuliani’s upbringing was complicated by his father’s criminal record, which included felony assault, robbery, and time in Sing Sing prison. His father later worked as an enforcer for a loan-sharking and gambling operation run by his brother-in-law.

• Early Education: The family moved to Garden City South on Long Island when Giuliani was seven. He attended St. Anne’s Catholic School before commuting back to Brooklyn for high school at Bishop Loughlin Memorial High School, graduating in 1961.

Higher Education and Career Foundations

• College Years: Giuliani attended Manhattan College, majoring in political science with a minor in philosophy. He was elected class president in his sophomore year and graduated in 1965. He briefly considered the priesthood before pursuing law.

• Law School: He studied at New York University School of Law, graduating cum laude with a Juris Doctor in 1968.

Early Legal and Political Career

• Political Beginnings: Giuliani began as a Democrat, working as a Democratic Party committeeman on Long Island in the mid-1960s and volunteering for Robert F. Kennedy’s 1968 presidential campaign. He voted for George McGovern in 1972.

• Clerkship and Military Deferments: After law school, he clerked for Judge Lloyd Francis MacMahon in the Southern District of New York. He avoided military service during the Vietnam War through student deferments and a high draft lottery number.

• First Steps in Law: In 1970, he joined the U.S. Attorney’s Office for the Southern District of New York. By 1975, he shifted his political allegiance—first to Independent, then Republican in 1980, citing disillusionment with Democratic policies.

• Private Practice: During the Carter administration, Giuliani practiced law at Patterson, Belknap, Webb and Tyler from 1977 to 1981.

Rise in Federal Law Enforcement

• Associate Attorney General: Under President Ronald Reagan, Giuliani became Associate Attorney General in 1981, overseeing federal law enforcement agencies.

• U.S. Attorney for the Southern District of New York: In 1983, Giuliani assumed this role, gaining prominence for prosecuting organized crime and Wall Street corruption.

  • Mafia Commission Trial: He indicted leaders of New York City’s Five Families under the RICO Act.

  • Wall Street Cases: Prosecuted Ivan Boesky and Michael Milken for insider trading and fraud.

  • Controversies: His use of the “perp walk” was criticized as excessive, and some high-profile cases were dismissed for lack of evidence.

Mayoralty of New York City (1994–2001)

• Election History: Giuliani lost to David Dinkins in 1989 but won in 1993 and was reelected in 1997 against Ruth Messinger.

• Policing and Crime:

  • Introduced “broken windows” policing with Police Commissioner William Bratton.

  • Implemented CompStat for data-driven crime reduction.

  • Crime rates fell significantly but civil rights groups criticized his policies for racial profiling.

• Civil Rights Controversies:

  • The torture of Abner Louima in 1997.

  • The fatal shooting of Amadou Diallo in 1999.

• Social Policies: Supported privatization of schools, protections for undocumented immigrants, and domestic partnership rights for LGBTQ+ couples.

• Senate Race and Personal Life: In 2000, he briefly ran for the U.S. Senate against Hillary Clinton before withdrawing due to prostate cancer and a public separation from Donna Hanover.

• September 11 Leadership: His crisis management during the attacks earned him worldwide recognition and the nickname “America’s Mayor.” Time magazine named him Person of the Year in 2001. Criticisms later arose regarding emergency preparedness, including placing the Office of Emergency Management inside 7 World Trade Center and inadequate protections for first responders.

• International Recognition: In 2002, Queen Elizabeth II awarded him an honorary knighthood.

Post-Mayoral Career and Business Ventures

• Giuliani Partners: Founded in 2002, the security consulting firm earned over $100 million in five years.

• Other Ventures:

  • Owned Giuliani Capital Advisors (later sold).

  • Joined Bracewell & Giuliani in 2005, working on legal and lobbying efforts, including defending Purdue Pharma in opioid cases.

  • Joined Greenberg Traurig in 2016 as cybersecurity chairman, resigning in 2018.

• International Lobbying: Advocated for Romanian political figures, opposed anti-corruption reforms, and supported the MEK exile group.

• Media and Public Life:

  • Launched the Rudy Giuliani’s Common Sense podcast in 2020.

  • Appeared on The Masked Singer in 2022 as “Jack in the Box.”

Political Campaigns and Trump Association

• Presidential Runs: Explored bids in 2008 and 2012, but his 2008 campaign collapsed after poor primary results. He endorsed John McCain.

• Ties to Trump:

  • Supported Trump’s 2016 campaign.

  • Served as Trump’s personal lawyer starting in 2018.

  • Involved in Ukraine dealings, including meetings with Andrii Derkach and lobbying for Dmytro Firtash.

  • Targeted by federal investigations, including a 2021 search warrant on his home and office.

• 2020 Election Challenges: Spearheaded Trump’s legal efforts to overturn results, promoting unverified fraud claims.

• Political Advocacy: Campaigned for his son Andrew’s 2022 gubernatorial run in New York.

Legal Issues and Recent Events (Up to September 2025)

• Law License: Suspended in 2021, fully disbarred in New York (July 2024) and Washington, D.C. (September 2024).

• Criminal Investigations: Named “Co-Conspirator 1” in the 2023 Trump indictment for election interference. Indicted in Georgia and Arizona for similar charges.

• Defamation Lawsuit: In December 2023, ordered to pay $148 million to Georgia election workers Ruby Freeman and Shaye Moss, leading to bankruptcy.

• Bankruptcy and Asset Forfeitures: Continues to face financial struggles in 2025 amid unresolved criminal cases.

Other Controversies and Public Life

• Trump-Ukraine Scandal:

  Prior to the 2020 election, Giuliani was a central figure in the Trump-Ukraine scandal, where he was allegedly involved in efforts to pressure Ukraine into launching an investigation into Joe Biden, a political rival of his client, Donald Trump. This led to a House impeachment inquiry against Trump.

• Post-Election Claims and the January 6th Capitol Attack:

  Giuliani was one of the most visible advocates for the false claims of widespread voter fraud following the 2020 election. He spoke at the rally preceding the January 6, 2021, attack on the U.S. Capitol and has been listed as an unindicted co-conspirator in the federal prosecution related to the alleged attempts to overturn the election.

• Financial and Personal Life:

  Reports indicate that Giuliani’s legal and financial troubles have taken a significant toll. He has attempted to raise funds through various means, including selling memorabilia and offering personalized video messages. His finances have come under scrutiny in his legal battles, with courts questioning his claims of financial hardship. He has also been involved in multiple divorces.

These recent developments stand in stark contrast to his earlier career as a successful federal prosecutor and his tenure as Mayor of New York City, particularly his lauded leadership after the 9/11 attacks, which earned him the moniker “America’s Mayor.”

Rudy Giuliani Age:

Rudy Giuliani was born on May 28, 1944, which makes him 81 years old as of September 2025. His zodiac sign is Gemini. He is a second-generation Italian American, as both of his parents, Harold and Helen Giuliani, were children of Italian immigrants. His nationality is American.

Rudy Giuliani Young:

Rudy Giuliani was born and raised in a working-class, Italian-American family in New York City. His early life and upbringing played a significant role in shaping his personal and political identity.

Parents: Harold and Helen Giuliani

Rudy Giuliani is the only child of Harold Angelo Giuliani and Helen (née D’Avanzo) Giuliani, both of whom were children of Italian immigrants.

• Harold Giuliani:

  A complex figure, Harold had a troubled past. He worked various jobs, including as a bartender and a bouncer. He was also involved in his brother-in-law’s loan-sharking and gambling business. Notably, Harold was arrested in 1934 for armed robbery and spent a year and a half in prison. Rudy Giuliani has stated that he only learned the full extent of his father’s criminal history later in life, and that Harold was deeply ashamed of his past. Harold instilled a strong sense of right and wrong in his son, emphasizing the importance of not stealing and always telling the truth. He was a devout Catholic who was determined to ensure his son had a better life.

• Helen Giuliani: Rudy’s mother, Helen, was a serious and intelligent woman who worked as a secretary. She was an anchor for the family and, along with Harold, emphasized the importance of hard work and education.

Upbringing and Early Life

Giuliani was born on May 28, 1944, in the East Flatbush neighborhood of Brooklyn, which was a predominantly Italian-American community at the time. His family was part of a large, tight-knit extended network of relatives. His grandmother lived with them, and other relatives, including his mother’s brother and his father’s sister (who were married to each other), lived nearby. This family structure fostered a strong sense of loyalty and mutual support.

When Rudy was seven, the family moved from Brooklyn to Garden City South on Long Island. This move was a deliberate choice by his father, who wanted to distance his son from the more unsavory elements of the family’s life in Brooklyn.

Rudy was raised a Roman Catholic and his education was entirely within Catholic schools. He attended St. Anne’s parochial school on Long Island, and then commuted back to Brooklyn to attend the prestigious Bishop Loughlin Memorial High School. After graduating in 1961, he attended Manhattan College, a Catholic institution, where he initially considered becoming a priest before deciding to pursue a career in law.

He had no siblings. The influence of his parents and his upbringing—a working-class family with a deep-seated respect for authority and a fierce dislike for organized crime, despite some family connections to it—is a central theme in many biographies of Giuliani’s life and career. His later reputation as a “mob buster” and a “tough on crime” mayor is often attributed to the lessons and values he learned during his formative years.

Rudy Giuliani Wife:

Rudy Giuliani’s personal life has been marked by three marriages, each of which ended in divorce. His marital history has often been the subject of public scrutiny, particularly during his political career.

First Wife: Regina Peruggi

• Marriage: Giuliani married Regina Peruggi in 1968. They had known each other since childhood, and their marriage was a long one, lasting until 1982.

• Annulment: The marriage was annulled in 1982 after Giuliani discovered that he and Peruggi were second cousins. This finding rendered the marriage invalid under Catholic Church doctrine. The annulment was granted in 1983.

Second Wife: Donna Hanover

• Marriage: Giuliani met Donna Hanover, a television news anchor, in the early 1980s. He proposed to her shortly after his legal separation from his first wife, and they were married in 1984.

• Children: They had two children, Andrew and Caroline Giuliani.

• Divorce: Their marriage came to a very public and contentious end. In 2000, while still mayor of New York City, Giuliani held a press conference to announce that he was separating from Hanover, reportedly without informing her beforehand. This was followed by a messy and highly publicized divorce proceeding. The divorce was finalized in 2002.

Third Wife: Judith Nathan

• Marriage: Giuliani’s relationship with Judith Nathan, a former nurse and medical sales executive, began while he was still married to Donna Hanover. Their relationship became a subject of intense media attention, particularly during his mayoral term. Giuliani and Nathan were married in 2003 at Gracie Mansion, with his friend Donald Trump in attendance.

• Divorce: The marriage to Judith (who now goes by Judith Giuliani) also ended in divorce. She filed for divorce in 2018 after 15 years of marriage. The divorce proceedings were also public and contentious, with reports of financial disputes. The divorce was finalized in 2019.

Rudy Giuliani Son:

Andrew Giuliani, Rudy’s son with Donna Hanover, is a former professional golfer who has also worked as an aide to President Donald Trump and has run for governor of New York.

Early Life and Public Presence

Born on January 30, 1986, Andrew Giuliani grew up in the public eye due to his father’s role as Mayor of New York City. A memorable moment from his childhood was at his father’s 1994 inauguration, where the 7-year-old was seen mimicking the oath of office and making animated gestures, which were later parodied on Saturday Night Live.

Golf Career

Andrew Giuliani was a talented golfer from a young age. He played on his high school team and later earned a spot on the Duke University men’s golf team. His time at Duke was not without controversy, as he was dismissed from the team and later sued the university, alleging minor infractions were used to justify his removal.

After college, he pursued a career as a professional golfer, playing on various minor league tours and even appearing on a reality television show. His most notable victory as a professional was winning the Metropolitan Open in 2009. He later sought to regain his amateur status in 2016.

Political and Media Career

In 2017, Andrew Giuliani shifted his focus to politics, joining the administration of President Donald Trump. He was hired as an associate director in the Office of Public Liaison and was later promoted to Special Assistant to the President. His role involved arranging visits for sports teams to the White House and serving as a liaison with various groups. He was also a regular golf partner for President Trump.

Following his time in the Trump administration, Giuliani worked as a contributor for the conservative news channel Newsmax TV. In 2021, he announced his candidacy for governor of New York in the 2022 election. His campaign heavily leaned on his family name and his support for Donald Trump. He ultimately lost the Republican primary to Lee Zeldin.

Rudy Giuliani Daughter:

Caroline Rose Giuliani, Rudy’s daughter with Donna Hanover, has pursued a career in filmmaking and has publicly distanced herself from her father’s political views.

She is a writer, filmmaker, and political activist. She is known for publicly and consistently disagreeing with her father’s politics, particularly his support for Donald Trump.

Education and Career

Caroline Giuliani attended Harvard University, where she studied theater and film production. After college, she pursued a career in the film industry, working as a production assistant on TV shows and films for networks like ABC and HBO. Her work as a filmmaker and writer often focuses on themes of mental health and human sexuality. She has been open about her own struggles with anxiety and an eating disorder.

Public Political Stance

A stark contrast to her father, Caroline is a vocal Democrat. This political difference has been a source of tension in their relationship. She publicly supported Barack Obama in 2008 and Hillary Clinton in 2016. In 2020 and 2024, she wrote essays for Vanity Fair magazine urging voters to support Democratic candidates Joe Biden and Kamala Harris, respectively. In these essays, she expressed her heartbreak over her father’s involvement with Donald Trump’s administration and described their relationship as “cartoonishly complicated.”

Personal Life

Caroline Giuliani has also been candid about her personal life. She has written about her journey to identifying as pansexual and her experiences with polyamory, which she calls “the unicorn life.” She stated that she is attracted to people based on their “presence and energy regardless of their biological sex, gender or gender identity.” In 2024, she announced her engagement to writer Mike Barker.

This video from MSNBC discusses how Caroline Giuliani’s political stance against Donald Trump is related to her father’s own struggles.

Rudy Giuliani Height:

Giuliani is reported to be about 5 feet 11 inches (180 cm) tall and his weight has been estimated at around 176 pounds (80 kg), though this has varied over the years.

Rudy Giuliani Disbarred:

In a major blow to his legal career, Rudy Giuliani has been disbarred in New York and Washington, D.C. The disbarment was a direct result of his actions following the 2020 presidential election. Courts found that he repeatedly made “false and misleading statements” about voter fraud while representing Donald Trump. The New York appeals court panel stated that Giuliani’s actions were a “flagrant misuse of his prominent position” and that he “deliberately violated some of the most fundamental tenets of the legal profession.”

Rudy Giuliani New York (NYC):

Giuliani’s career began in the U.S. Attorney’s office in New York. He quickly rose through the ranks, gaining a reputation for his aggressive and successful prosecution of high-profile cases. As the U.S. Attorney for the Southern District of New York from 1983 to 1989, he became famous for taking on the Mafia’s “Five Families” using the RICO Act. He was also credited with a record of 4,152 convictions with only 25 reversals. His reputation as a “tough on crime” prosecutor was a key factor in his successful mayoral campaigns.

Rudy Giuliani Lawsuit:

Rudy Giuliani Settlement:

Rudy Giuliani has reached a settlement with two Georgia election workers, Ruby Freeman and her daughter, Wandrea “Shaye” Moss, to satisfy a $148 million defamation judgment against him. This agreement brings an end to a long legal battle that began after Giuliani’s false claims about the women’s role in the 2020 presidential election.

Terms of the Settlement

• Financial Compensation: The agreement includes financial compensation to Freeman and Moss, but the specific amount was not disclosed publicly.

• Retention of Assets: The most notable part of the settlement is that it allows Giuliani to retain some of his most valuable assets, including his New York co-op and Florida condominium. His son, Andrew Giuliani, also gets to keep three World Series rings that were at stake. This was a key goal for Giuliani’s legal team, who were trying to prevent the full-scale seizure of his property.

• No Admission of Guilt: Giuliani stated that the settlement does not involve an “admission of liability or wrongdoing.”

• Non-Defamation Agreement: Both parties agreed not to defame each other in the future.

Context of the Legal Battle

The settlement was reached in January 2025, just as a trial was set to begin to determine how much of Giuliani’s property could be seized to satisfy the initial judgment. The women had been seeking all of his assets to fulfill the $148 million verdict awarded to them by a jury in December 2023.

Giuliani had filed for bankruptcy days after the verdict, an action widely seen as a way to avoid paying the full amount. However, a judge later dismissed his bankruptcy case, putting his assets at risk. The settlement ultimately provided a resolution, allowing both sides to avoid a protracted legal fight over his remaining property.

Rudy Giuliani Health:

Rudy Giuliani has had several public health issues throughout his life, including a serious bout with cancer and, more recently, a car accident. These health challenges have at times intersected with his political career and public image.

Prostate Cancer

In April 2000, while he was serving as mayor of New York City and contemplating a run for the U.S. Senate against Hillary Clinton, Giuliani was diagnosed with prostate cancer. The diagnosis was a major life event that ultimately led him to drop out of the Senate race.

• Diagnosis and Treatment: The cancer was discovered at an early stage during a routine physical. Giuliani, whose father also died of prostate cancer, opted for a combination of hormone therapy and radiation, specifically brachytherapy (radioactive seed implants) and external beam radiation. He chose this course of treatment over surgery to minimize potential side effects.

• Public Advocacy: Following his successful treatment, Giuliani became a prominent advocate for prostate cancer awareness. He spoke openly about his experience and urged men to get screened, emphasizing that early detection saved his life. He became the honorary chairman of the National Prostate Cancer Coalition, using his public platform to educate others about the disease.

COVID-19 Diagnosis

In December 2020, during the height of the COVID-19 pandemic, Rudy Giuliani tested positive for the virus. He was hospitalized for a time at Georgetown University Medical Center. His diagnosis came while he was traveling extensively across the country, often without a mask, to challenge the results of the 2020 presidential election on behalf of Donald Trump.

Rudy Giuliani Recent Injuries from a Car Accident

On a recent Saturday evening in late August 2025, Rudy Giuliani, at 81 years old, was seriously injured in a car accident in New Hampshire.

Details of the Accident and Injuries

According to his spokesperson, Michael Ragusa, Giuliani was a passenger in a rental car on a highway near Manchester when the vehicle was struck from behind at high speed. The impact pushed both vehicles into the median.

Giuliani was transported to a nearby trauma center, where he was treated for several injuries, including:

• A fractured thoracic vertebra (a bone in the upper back).

• Multiple lacerations and contusions.

• Injuries to his left arm and lower leg.

The driver of his car, his spokesperson Ted Goodman, and the 19-year-old driver of the other vehicle also sustained injuries, but all were reported to be non-life-threatening.

Circumstances Surrounding the Crash

Giuliani’s team stated that the crash was not a targeted attack and was, in fact, “entirely unrelated” to an event that occurred just prior. According to his spokesperson, Giuliani had been flagged down by a woman who was a victim of domestic violence. He assisted her, contacted 911, and stayed on the scene until police arrived to ensure her safety. It was shortly after he resumed his travel that the accident occurred.

Prognosis and Recovery

Despite the severity of his injuries, Giuliani’s team has reported that he is in “good spirits and recovering tremendously.” He is expected to remain hospitalized for a few days for further tests and stabilization, and he will need to wear a brace to support the fractured vertebra. Given his age, recovery is expected to require pain management and physical therapy.

Speculation on Cognitive Health

Due to his at times erratic behavior, slurred speech, and public gaffes, particularly in recent years, Giuliani’s cognitive health has been a frequent subject of public speculation and criticism. This speculation has not been confined to media pundits; political opponents and even some legal observers have questioned his mental state. It’s important to note, however, that these are public observations and not a medical diagnosis.

Rudy Giuliani in Drag:

Rudy Giuliani’s public appearances in drag are well-documented and have become a notable part of his history, particularly in light of more recent political controversies surrounding drag performances.

A Comedy Skit with Donald Trump

The most famous instance of Giuliani in drag is a skit he performed with Donald Trump in 2000. The performance was part of the Mayor’s Inner Circle Press Roast, an annual charity event where New York politicians and journalists perform skits to parody themselves.

• The Skit: In the skit, Giuliani, dressed in a wig, a sparkly gown, and makeup as his drag persona “Rudia,” flirts with a man who is revealed to be Donald Trump. The sketch culminates with Trump pushing his face into Giuliani’s fake breasts. Giuliani’s character reacts with a playful slap, exclaiming, “Oh, you dirty boy, you! Donald, I thought you were a gentleman!”

• Context and Resurfacing: The video was a humorous moment in a different political era. It has since resurfaced repeatedly, especially during the 2016 presidential election and again more recently. The clip is often used by critics to highlight what they see as hypocrisy, as Giuliani and other Republicans have taken strong stances against drag performances, particularly those in the presence of children.

Other Public Drag Appearances

While the skit with Trump is the most famous, Giuliani has appeared in drag on other occasions. For example, he has appeared on Saturday Night Live and in other comedy skits. These appearances were generally seen as a part of his public persona as a larger-than-life figure who could be both a serious politician and a self-deprecating humorist.

In recent years, Giuliani’s past in drag has taken on a new political meaning. As debates around drag and gender identity have become central to American politics, images and videos of his performances have been used to challenge his current political positions and those of his allies.

Rudy Giuliani Four Seasons:

On November 7, 2020, just as media outlets were calling the presidential election for Joe Biden, Rudy Giuliani held a press conference to announce the Trump campaign’s legal challenges to the results. The event was scheduled at an unusual location: Four Seasons Total Landscaping, a small landscaping business in a working-class neighborhood of Philadelphia, rather than the luxurious Four Seasons Hotel in downtown Philadelphia.

Background and Details:

• The Mistake:

  The incident began with a now-famous tweet from Donald Trump that initially stated a “big press conference” would be held at the “Four Seasons, Philadelphia.” The tweet was quickly deleted and replaced with a correction: the event would be at “Four Seasons Total Landscaping!” The Four Seasons Hotel in Philadelphia quickly issued a clarifying tweet, stating it had “no relation with the hotel.”

• The Location:

  The choice of venue was immediately ridiculed. It was an unassuming location, an industrial park situated between a crematorium and a sex shop. Journalists and the public quickly created a flurry of jokes and memes about the bizarre scene. The fact that Giuliani was speaking in a gravel parking lot with a chain-link fence behind him, rather than the grand ballroom of a luxury hotel, became a powerful symbol of the Trump campaign’s disorganized and failing legal efforts.

• The Timing:

  The surreal nature of the event was amplified by its timing. As Giuliani began speaking, news organizations announced that Joe Biden had won the election. Reporters on the scene even shouted the news to Giuliani, who responded by saying, “The networks don’t get to decide elections, courts do.”

• Aftermath:

  The gaffe became an enduring meme and a lasting part of the 2020 election narrative. The landscaping company, Four Seasons Total Landscaping, cleverly embraced its newfound fame, selling merchandise emblazoned with slogans like “Make America Rake Again.”

Rudy Giuliani Masked Singer:

In 2022, Rudy Giuliani made a surprise and highly controversial appearance as a contestant on the reality singing competition show, The Masked Singer. His unmasking as “Jack in the Box” caused two of the show’s judges, Ken Jeong and Robin Thicke, to walk off the set in protest.

Details of the Incident:

• The Performance and Reveal:

  Giuliani, dressed in a jack-in-the-box costume, performed a rendition of “Bad to the Bone” by George Thorogood and the Destroyers. When he was eliminated and unmasked, two of the judges, Ken Jeong and Robin Thicke, were so taken aback that they immediately left the stage. Jeong, an actor and comedian who is also a licensed physician, was visibly upset and later stated he felt “disrespected” by the show’s decision to cast someone who he believed had spread misinformation about the COVID-19 pandemic.

• The Controversy:

  The incident created a significant public backlash. Critics of the show argued that providing a platform for Giuliani, a polarizing political figure who was facing numerous legal challenges and had made false claims about the 2020 election, was irresponsible and insensitive. The reveal was seen by many as a cheap ratings stunt that crossed a line by normalizing a figure central to many political controversies.

• Network Response:

  Fox executives defended the decision, arguing that the show’s identity is built on delivering “jaw-dropping moments” and that Giuliani’s casting perfectly fit that mold.

Rudy Giuliani Borat 2:

Giuliani’s appearance in the 2020 mockumentary film Borat Subsequent Moviefilm generated significant controversy. He was filmed in a hotel room with actress Maria Bakalova, who was posing as a journalist. The scene showed Giuliani lying on a bed with his hand down his pants, which he and his team claimed was an innocent act of tucking in his shirt after taking off his microphone. Critics and commentators, however, viewed the scene as highly inappropriate and damning.

Details of the Scene and Controversy:

• The Setup:

  Sacha Baron Cohen’s film is a mockumentary that uses hidden cameras to satirize political figures. In the scene, actress Maria Bakalova, who plays Borat’s daughter, Tutar, poses as a conservative journalist to interview Giuliani in a hotel room.

• The Scene Itself:

  After the interview concludes, Bakalova suggests they “have a drink in the bedroom.” Giuliani follows her, and after she helps him remove his microphone, he is seen reclining on the bed with his hand in his pants. At this point, Sacha Baron Cohen, in character as Borat, bursts into the room and shouts, “She’s 15. She’s too old for you!” (Bakalova was 24 at the time).

• Giuliani’s Defense:

  Giuliani vehemently denied any wrongdoing. He and his team claimed he was simply “tucking in his shirt after taking off the recording equipment.” He called the scene a “complete fabrication” and claimed it was part of a coordinated attack against him for his work on behalf of Donald Trump.

• Public Reaction:

  The scene became a viral clip and was widely condemned as inappropriate. The footage was released just weeks before the 2020 presidential election, adding to the political tumult of the time. While Giuliani’s explanation was dismissed by many, the incident once again placed him at the center of a public scandal that garnered global attention.

Rudy Giuliani Coffee:

Rudy Giuliani has entered the coffee business, launching his own brand called “Rudy Coffee.” This new venture has garnered significant attention, not just for the product itself, but for the circumstances surrounding its launch.

Launch and Marketing

Giuliani officially launched his coffee brand in May 2024. The product line includes three blends:

• “Rudy Organic Morning Coffee”

• “Rudy Organic Bold Coffee”

• “Rudy Organic Swiss Water Decaf Coffee”

The coffee is marketed with slogans and imagery that tie directly into Giuliani’s political and public persona. His website, for instance, offers products with taglines like “America’s Mayor,” “Fighting for Justice,” and “Enjoying Life,” often accompanied by images of Giuliani himself. He has promoted the coffee through his social media channels, claiming it’s “quality you can trust” and that it’s a “delicious fresh roasted specialty coffee” with health benefits.

Context of the Venture: Financial and Legal Troubles

The launch of “Rudy Coffee” comes at a time of immense financial and legal pressure for Giuliani. The venture is widely seen as an attempt to generate income to pay off a mountain of debt, including a massive $148 million defamation judgment he was ordered to pay to two Georgia election workers, Ruby Freeman and Shaye Moss.

• Bankruptcy: Giuliani filed for Chapter 11 bankruptcy in December 2023, just days after the defamation judgment was announced.

• Legal Scrutiny: The coffee brand has come under legal scrutiny from Giuliani’s creditors, who have argued in court that the business is an “alter ego” of Giuliani himself. This means that the court could potentially seize the company’s profits to satisfy his legal debts, an attempt to prevent him from using the business to shield assets. A federal judge has criticized Giuliani’s attempts to use the company to protect his assets from the defamation lawsuit.

In this respect, “Rudy Coffee” is similar to other ventures by figures in Donald Trump’s circle who have used branded products—from sneakers to books to coffee—to fund their legal battles.

Rudy Giuliani Hair Dye:

On November 19, 2020, Rudy Giuliani held a press conference at the Republican National Committee headquarters in Washington, D.C., to discuss the Trump campaign’s claims of widespread voter fraud in the presidential election. However, the event quickly became a viral sensation for a reason unrelated to his legal arguments.

The Incident

As Giuliani spoke passionately at the podium, visibly sweating under the bright camera lights, a dark, liquid substance began to streak down both sides of his face. The substance was widely believed to be hair dye, which was sweating off and running down his cheeks, creating a bizarre and widely mocked image.

• Public Reaction:

  The incident was immediately noticed by a live audience, and videos and images of the dripping dye spread rapidly across social media platforms. News outlets and late-night talk shows seized on the moment, turning it into a symbol of the chaos and perceived disarray of the Trump legal team’s efforts. The visual gaffe was seen by many as a perfect metaphor for the unproven and flimsy nature of the claims he was making.

• A “Freak Show”:

  According to reports, even some of Giuliani’s colleagues and those in the Trump White House were taken aback by the incident. A staffer reportedly described it as a “freak show,” and some books written about the Trump administration’s final days noted that even Donald Trump was reportedly “pissed” by the scene, as it undermined the message of the press conference.

The “hair dye” moment became a defining image of Giuliani’s post-election campaign, overshadowing his legal arguments and adding to a series of high-profile public gaffes, including the Four Seasons Total Landscaping press conference and the Borat 2 hotel room scene.

Rudy Giuliani and Maria Ryan:

Rudy Giuliani’s relationship with Maria Ryan, a former hospital executive and nurse practitioner, has been a subject of public scrutiny, particularly due to conflicting statements about the nature of their connection. While both have publicly described their relationship as strictly professional, legal filings and leaked recordings have cast doubt on that claim.

The Public and Professional Relationship

Maria Ryan and Rudy Giuliani have been closely associated for several years. She has been described as a business partner, co-host of his podcast, and a medical adviser. She has been seen with him at numerous public and political events, including a state dinner at the White House in 2019. In a recent statement following Giuliani’s car accident, his spokesperson stated that Ryan was a “board-certified nurse practitioner” who was overseeing his care and that they were “business partners and nothing more.”

The “Alleged Girlfriend” Controversy

The nature of their relationship came under intense scrutiny during Giuliani’s 2023 bankruptcy case and a separate sexual harassment lawsuit filed by a former employee, Noelle Dunphy.

• Bankruptcy Filings:

  In legal documents related to the bankruptcy case, lawyers for Giuliani’s creditors referred to Ryan as his “alleged girlfriend” and questioned whether she was involved in hiding his assets. The filings showed that Giuliani had paid off her credit card bills, which Ryan claimed were reimbursements for her covering his own grocery and medical expenses.

• Secret Recordings:

  As part of her lawsuit, Dunphy submitted secret recordings of Giuliani in which he allegedly discussed his relationship with Ryan. In these recordings, he reportedly described a two-year affair with a woman who “loves me, but she can’t leave her family, including her husband.” He also allegedly spoke about a “weird” dynamic where he was friendly with Ryan’s husband, Bob Ryan, and had even had Thanksgiving dinner with them.

• Denials:

  Both Giuliani and Ryan have consistently denied the claims of a romantic relationship. Ryan has stated she considers Giuliani one of her “best friends” and that she is “not his girlfriend.”

Rudy Giuliani Net Worth:

Rudy Giuliani’s net worth has fluctuated dramatically over the years, and he is currently in a state of severe financial distress due to extensive legal debts.

Past Wealth

For a long period, particularly after his tenure as New York City mayor, Giuliani was a very wealthy man. His net worth was estimated to be over $50 million, and in some financial disclosures, he listed his assets as being worth between $18.1 million and $70.4 million.

This wealth came from several sources:

• Speaking engagements: He was a highly sought-after public speaker, reportedly earning as much as $100,000 per speech.

• Business Ventures: He founded Giuliani Partners, a security consulting firm, which landed lucrative contracts around the world. He also worked with several prominent law and lobbying firms.

• Investments: He made significant money from various investments, including a reported $30 million from the sale of a data company he represented.

Current Financial Situation

In recent years, Giuliani’s financial situation has deteriorated dramatically due to mounting legal fees and, most significantly, a massive defamation judgment against him.

• Defamation Judgment: In December 2023, a jury ordered Giuliani to pay two Georgia election workers, Ruby Freeman and Shaye Moss, $148 million in damages for defamation.

• Bankruptcy Filing: Days after the verdict, Giuliani filed for Chapter 11 bankruptcy. In his filing, he estimated his assets were between $1 million and $10 million, but his liabilities were between $100 million and $500 million.

• Dismissed Bankruptcy: A judge later dismissed Giuliani’s bankruptcy case, citing his uncooperative conduct. This move put his remaining assets, including his homes and other valuables, at risk of being seized to pay off his debts.

As of today, his net worth is not definitively known, but it is clear that his assets are dwarfed by his legal debts. His financial situation is so dire that he has resorted to selling branded coffee and other merchandise to generate income, and his legal team has been working to negotiate settlements to prevent the total liquidation of his assets.

Is Rudy Giuliani in jail?

No, Rudy Giuliani is not currently in jail. He has faced multiple indictments, including in Georgia and Arizona, but he has pleaded not guilty and has not been convicted or sentenced to prison.

Is Rudy Giuliani Married?

No, Rudy Giuliani is not currently married. His last marriage to Judith Nathan ended in a 2019 divorce.

What happened to Rudy Giuliani’s son?

Andrew Giuliani has pursued his own public career, primarily in politics and media. He has worked for the Trump administration, served as a political commentator, and ran an unsuccessful campaign for governor of New York.

How Old Is Rudy Giuliani?

Rudy Giuliani was born on May 28, 1944. As of today, September 1, 2025, he is 81 years old.

What did Rudy Giuliani do?

Giuliani’s long career has seen him transition from a high-profile prosecutor who took down the Mafia to a celebrated mayor who led New York after 9/11. More recently, as a personal attorney for Donald Trump, his actions in challenging the 2020 election results have led to his disbarment and numerous legal and financial problems.

What happened To Rudy Giuliani?

The last few years have been turbulent for Rudy Giuliani. He has been at the center of numerous legal and political controversies stemming from his work for Donald Trump. These have led to his disbarment, significant financial debt, and an ongoing series of lawsuits and criminal charges.

Where is Rudy Giuliani today?

Giuliani is still a public figure and a frequent subject of media attention due to his ongoing legal battles. He continues to appear on his radio show and podcast and is often seen in court, managing his various legal cases.

Sources & notes

• Wikipedia: Rudy Giuliani (summary & career).

• New York Appellate Division disciplinary opinion (disbarment PDF).

• AP / Reuters / ABC / NBC coverage (defamation judgment, settlement, disbarment, Georgia charges).

• Coverage of Borat scene: The Guardian, BBC and other mainstream outlets.

• Four Seasons Total Landscaping reporting: The Guardian, New York Magazine, Vanity Fair.

• Masked Singer / entertainment press coverage (Deadline / People / Wikipedia).

• Recent accident coverage (AP, The Guardian, Reuters).