Rudy Giuliani: Moments Great And Small

Rudy Giuliani was elected as the mayor of new york city

Rudy Giuliani: Moments Great And Small

By D.S. Mitchell and Michael Leonard Douglas

Chances Offered

Rudy Giuliani has great moments and small

Most men are offered only one chance at greatness. Fewer men yet rise to extraordinary levels of heroism to be followed by extraordinary levels of greed, depravity, and personal and political immorality. But, Rudy Giuliani isn’t your average guy.


Rudolph William Louis Giuliani was born in East Flatbush, Brooklyn, borough of New York City, N.Y. May 28, 1944. Rudy was the only child of working class parents Harold Angelo Giuliani and Helen D’Avanzo Giuliani. Both parents were children of Italian immigrants. Rudy Giuliani’s large extended family was mostly made up of criminals, cops and firefighters. “I grew up with uniforms all around me,” he has reportedly said.

Secrets Exposed

Rudy's father spent 18 months in Sing Sing for felony robbery and assault

Rudy’s father spent 18 months in Sing Sing for robbery and assault before Rudy’s birth

In 1934, ten years before Rudy Giuliani’s birth, his father was arrested for robbing a milkman at gunpoint.  He was later convicted of felony assault and robbery. He served 18 months at Sing Sing, a maximum security prison in New York state. When he was released from prison he had trouble finding employment and ended up “working as an enforcer for his brother-in-law Leo D’Avanzo. D’Avanzo ran an organized crime operation involved in loan sharking and gambling” (Wikipedia).

A Move 

To Harold Giuliani’s credit he moved his small family from East Flatbush to Long Island to distance his son from the mob connected members of the family. In fact, Rudy Giuliani remembers his father constantly reinforcing a deep respect for law and order. “He made sure that I didn’t repeat his mistakes-which I thank him for, because it worked out” (


Rudy Giuliani received his early education at St. Anne’s a local Catholic elementary school. He attended Bishop Loughlin Memorial High School. He was an average to mediocre student, graduating in 1961. Despite being a less than enthusiastic student Giuliani was an organizer and class politician. By the time of graduation he had begun to think about entering the priesthood. Giuliani went on to study at Manhattan College in the Bronx. He studied political science and philosophy.

The Law

Rudy Giuliani chose law over the priesthood

Rudy Giuliani chose law over the priesthood

After a less than stellar high school and undergraduate college career Rudy Giuliani discarded his intent to enter the priesthood and decided to pursue a law degree. Rudy took to the law like the proverbial duck to water. He graduated from New York University School of Law cum laude with a Juris Doctorate in 1968.  After excelling at his law studies he earned him a prestigious law clerk position with Judge Lloyd Francis MacMahon.  MacMahon was a U.S. District Judge for the Southern District of New York.

Beginning Career

When his clerkship with Judge MacMahon ended the judge recommended Rudy Giuliani for a position in the U.S. Attorney’s Office in Washington, D.C.  In 1973, at age 29, Giuliani was appointed the attorney in charge of police corruption cases resulting from the Knapp Commission. He worked under Harold “Ace” Tyler.  In 1977 he left the U.S. Attorney’s Office to work in private practice. He was hired  as an associate at Tyler’s prestigious New York law firm, Patterson, Belnap, Webb & Tyler.

Exaggerated  Self-Image

Just three years later he returned to public service. He was tapped by President Ronald Reagan to become the number 3 at the  Department of Justice. In 1983 Giuliani was appointed U.S. attorney for the Southern District of New York. The SDNY is one of the most visible and prestigious U.S. attorney’s office in the country.  It was a  natural fit. Rudy’s style of news conferences and camera-ready prosecutions made him a natural. Harold “Ace” Tyler who worked with Rudy Giuliani in private practice and at the DOJ described Giuliani’s tactics as “overkill” (Time Magazine).

Record Setting

At the SDNY Rudy Giuliani’s efforts were mostly directed at the prosecution of white-collar lawbreakers, organized crime, and corruption within various government institutions. His conviction record was astounding. He became one of the most revered U.S. attorneys in American history. Rudy Giuliani was responsible for a total 4,152 successful convictions. He had a mere 25 reversals. However, his many critics saw him as a boisterous  grand-stander. In several high-profile cases he had people arrested and paraded before cameras for the 6 o’clock news shows. He would later quietly drop the charges.

Taking On The Mafia

Rudy Giuliani was instrumental in mafia convictions

Rudy Giuliani was instrumental in mafia convictions dramatically weakening the “5 Families”

Between 2/25/1985 and 11/19/1986 Rudy Giuliani became the most famous prosecutor  in America. Giuliani played center stage on the high-profile Mafia Commission trials.  Using the RICO (Racketeer Influenced and Corrupt Organizations Act) he indicted 11 organized crime figures including heads of the “Five Families”. He summed up the indictments this way, “Our approach is to wipe out the five families”.

Death In The Street

Some crime figures were skipped over for prison time when they were murdered

Paul Castellano skipped a prison sentence by being murdered on a Manhattan street

The RICO statutes allowed arrests for conspiracy to commit extortion, labor racketeering, and murder for hire. Three heads of the Five Families were sentenced to over 100 years of prison time. In two separate trials the Genovese and Colombo leaders received respectively 70 year terms and a 39 year sentence. The Gambino crime family boss, Paul Castellano escaped a jail sentence when he was murdered on the street in midtown Manhattan. During this time according to FBI internal documents, the Sicilian Mafia offered $800,000 for the murder of Giuliani. The Colombo and Gambino heads are also said to have contracted for Rudy Giuliani’s killing.

Vesuvian Temper

In September 1989 Rudy Giuliani resigned from the U.S. Attorney’s Office. There were many people who were more than happy to see him go. Many were critical of his methods of handling cases. He was accused of making prosecutorial decisions based on his political ambitions. His infamous bad temper and rude retorts to questions from the media were part of a growing negative persona.

Mayor Candidate

By 1989, Rudy Giuliani had been a Democrat, an Independent and finally a Republican.  His first run at political office came that same year. Giuliani decided to run against Democrat David Dinkins for mayor of New York. Now a registered Republican, Giuliani ran a robust campaign. It was the closest election in New York city history. Dinkins won and became the first black mayor of New York City.

Another Mayoral Run

In 1993, Rudy Giuliani challenged Dinkins again. Times had changed. New York was facing a crime wave and Giuliani eagerly beat the “tough on crime” drum that appealed to many voters.  This time, Giuliani beat Dinkins decisively. Rudy Giuliani in his megalomaniac way took on the task of cleaning up the streets with formidable zeal.

Broken Window Methodology

Giuliani and Bratton instituted the broken window theory of policing

Giuliani and Bratton instituted the broken window theory of policing leading to enforcement of ‘quality of life’ laws.

Rudy Giuliani and Police Commissioner William J. Bratton implemented a “broken windows” theory of policing. Basically meaning you start with the small offenders.  The core idea holds that “minor disorders and violations create a permissive atmosphere that leads to more serious crimes. To prevent major crime, the theory holds the police should enforce seemingly minor ‘quality of life laws’ such as  public drinking, littering and jaywalking-” (Wikipedia).

Law Enforcement

Crackdowns on graffiti, turnstile jumping, cannabis possession, panhandlers and street peddling were initiated by Rudy Giuliani.  Computer driven crime mapping using a statistical approach was used to identify “criminal patterns” and “crime zones.” Computer mapping also measured police performance. Such methods would later draw sharp criticism for encouraging manipulation of crime data.  Although a persistent topic by his critics, no evidence of data manipulation was ever proven.

William Bratton

Rudy Giuliani and his Police Commissioner, William Bratton , introduced tough policies that saw a dramatic reduction in crime rate within his first two years in office. Police shootings were reduced by 40%. Cases of jail violence in the city dropped 95%.  Giuliani introduced a welfare-to-work system that is credited with moving 691,000 people off the welfare rolls. Large areas of the city were marked for renewal development. Property values rose dramatically across the city. The results were  dramatic.  After two years, the bombastic Bratton was forced out by Giuliani. It seems the pugilistic mayor grew tired of Bratton’s headline grabbing personality.


Rudy's policies brought out protesters

Rudy’s policies mobilized activists on every issue, particularly issues for black citizens

Rudy Giuliani was just as confrontive and adversarial as mayor as he had been as a U. S. Attorney.  He gained enemies and critics quickly. There was an unending backlash from minority leaders who argued that NY city cops were relying on racial profiling. Officials of the compromised New York city public school system complained loudly that Giuliani focused more on incarceration rates than the welfare of the city’s children. Many critics accused Giuliani of hammering everyone else into submission with frequent outburst of temper and bad behavior. He attempted to marginalize resistance; particularly by minority activists like the Reverend Al Sharpton.

1997 Election

For his re-election bid,  Giuliani was able to cobble together support from white Catholics, Jews and gay voters.  He soundly defeated Democratic challenger Ruth Messinger. .After winning his second term he saw a continuing eroding of his popularity; especially towards the end of his second term.  As time wore on his tactics became increasingly unpopular. Despite the decline in crime rate, people saw his methods as unacceptable. He was accused of racial discrimination.  “Stop and frisk” were standard police tactics.


During his time as mayor, the cases of three black men shocked the nation. Abner Louima, Amadou Diallo and Patrick Dorismond suffered the harsh consequences of Rudy Giuliani’s policies. In 1997, Louima was physically tortured by police. He was beaten and suffered such atrocities as having a mop handle inconveniently shoved up his rectum while in police custody.  An unarmed Amadou Diallo was shot 41 times by police in 1999. In 2000, Patrick Dorismond another unarmed black man was shot by the police outside a bar during a scuffle initiated by two undercover cops. These three cases cost New York city nearly $12,000,000.

HRC and Senate Run

Hillary Clinton was recruited by Democrats to run for David Patrick Moynihan's vacant NY senate seat.

Hillary Clinton was recruited by the Democrats to run for David Patrick Moynihan’s vacant NY senate seat

When Democratic Senator Daniel Patrick Moynhan announced his retirement from the U.S. Senate Giuliani decided he’d throw his hat into the race. Republicans hoped the high-profile mayor would be able to secure the New York senate seat for Republicans. The Democrats recruited former first lady Hillary Rodham Clinton to enter the race.  It looked like Rudy Giuliani and Clinton were going to go head to head for Moynihan’s now open senate seat. The polls for each were an up and down affair, with the two opponents exchanging the lead from week to week.

Slowing Down

His efforts to improve New York City were in many ways remarkable. However, Rudy Giuliani was not adored or respected.  In the Spring of 2000, over the period of four weeks, Giuliani’s life exploded in scandalous headlines.   His medical health, his marriage, his extramarital affairs and his political life nose-dived on to the national stage.  Giuliani was diagnosed with prostate cancer in 1997. He quietly underwent treatment. During that time he began a love affair with Judith Nathan. His affair with Judith Nathan became media fodder as the media turned his extramarital life into a three-ring circus.

Using The Media

Politically Giuliani watched his poll numbers plummet. Faced with decreasing popularity he announced his withdrawal from the U.S. Senate race. In fact, still using the media, Giuliani announced his plan to divorce his wife Donna Hanover. Unfortunately he had failed to notify his wife of his planned divorce.

Moved Out

Rudy Giuliani announced his divorce on television before advising his wife

Rudy Giuliani announced his pending divorce on television before telling his wife the news

The TV announcement aggravated the already stressed marriage.  His behavior was tacky to say the least.  After the on-screen divorce pronouncement Donna obtained a restraining order keeping Rudy from entering the New York City mayor’s official residence, Gracie Mansion. The homeless Rudy ended up in car dealer Howard Koeppel spare bedroom.

Limping Into The Fall

As September 2001 marched forward Rudy Giuliani was a lame duck mayor waiting for his November replacement. He had been locked out of Gracie Mansion, and his personal reputation was in tatters. It was amidst this chaos that destiny tapped Rudy on the shoulder. On 9/11/2001 the United States was attacked by al Qaeda  At the time, al Qaeda was the most well-known Muslim terrorist group in the world. The terrorist group headed by Osama bin Ladin was suspected of the bombing of U.S. embassies in Kenya and Tanzania.

Hijackers Kill Thousands

On “9/11” two commercial aircraft piloted by suicide hijackers plowed into the Twin Towers of the World Trade Center. A third commercial airliner careened into the Pentagon in Washington, D. C. The fourth and last commercial hijacked plane did not reach its target. The fourth plane, was believed headed toward the U.S. Capital building.  That plane was forced down in a Pennsylvania field. Outraged passengers risked their lives to overwhelm the hijackers and bring the plane down changing the hijackers plans to wipe out the legislative branch of the U.S. government.

Holding A City Together

Rudy Giuliani arrived at the World Trade Center scene moments after the second plane crashed into the south tower. He watched as bodies dropped from the collapsing buildings.  “Giuliani coordinated rescue operations that may have saved 20,ooo lives and emerged as the national voice of reassurance and consolation” (

Rudy’s Churchill Moment

Rudy Giuliani had his finest moment at 9/11

Rudy Giuliani had his finest hour on 9/11

“Tomorrow New York is going to be here,” a somber but resolute Rudy Giuliani announced to the city, the nation, and the world.  “And we’re going to rebuild, and we’re going to be stronger than we were before.  I want the people of New York to be an example to the rest of the country, and the rest of the world, that terrorism can’t stop us-” (Time Magazine).

Defying History

Being at the scene, Rudy Giuliani was viewed as a symbol of comfort and faith. Rudy Giuliani provide a mourning city and country with a face of optimism and courage. Giuliani perceived himself the Winston Churchill of America. The Queen of England was watching. The Queen was so damn impressed with his actions that she knighted Rudy Giuliani in October 2001.

Defining History

The attacks were the deadliest terrorist attacks in world history. In addition, it was the most devastating foreign attack on U.S. soil since the Japanese attack on Pearl Harbor 12/7/1941. The 19 hijackers were killed. With the hijackers 2,977 people were also killed. Over 6,000 people were injured.

Ground Zero

After his memorable leadership on 9/11, Rudy Giuliani found himself in trouble once more. His administration was accused of failing to protect rescue workers at the scene of the 9/11. With long-term health issues at hand, ground zero  workers accused Rudy Giuliani’s administration of failing to protect them during the evacuation process. They sued the city and got a settlement that totaled a whopping $600 million in payouts. The basis of the suit was that the City hurriedly approved the evacuation process without following safety protocols to safeguard evacuation officers.

Life After 9/11

Rudy Giuliani operates a cybersecurity firm. Some say it is more of a lobbying firm

Rudy Giuliani claims he operates a cybersecurity firm. Most call it an international lobbying firm.

In 2002 he started Giuliani Partners. The company claims to offer a full array of management consulting and cybersecurity services. There is no doubt that Rudy Giuliani brings star power to any business he is involved with.  That’s why it’s called Giuliani Partners.  Rudy Giuliani became a household name after the 9/11 tragedy. Although no longer in political office Giuliani has kept himself in the public eye. He made a feeble attempt at a 2008 run for the Republican presidential nomination. During that race he was roundly condemned for his blatant and repeated use of the 9/11 catastrophe to perpetuate his reputation.

To Lobby, Or Not To Lobby

One question that keeps coming up in regards to Giuliani Partners is what does Giuliani know about cybersecurity? Just about nothing, is the typical and most correct response. Most have written off Giuliani Partners self-described security service as a farce. Instead, most describe the company as an international lobbying firm. The multi-million dollar company is under scrutiny for some questionable dealings.  From terrorism ties to falsified drug dealings, Giuliani Partners has remained in the spotlight for all manner of negative media attention.

Bracewell & Giuliani

In 2005 Giuliani joined Bracewell & Patterson, a Texas law group. The firm was renamed Bracewell & Giuliani LLP. Giuliani opened a New York office. Bracewell “was a high-profile supplier of legal and lobbying services to the oil, gas, and energy industries-” (Wikipedia) The firm became well-known for its aggressive defense of pollution-causing coal-fired power plants. Rudy Giuliani drew criticism as the  company front man.

Trump Campaign

Rudy Giuliani jumped on the Trump bandwagon early

Giuliani jumped on the Trump bandwagon early and wanted to be Attorney General, but it was not to be and he ended up on the legal team

In the 2016 presidential campaign, Rudy Giuliani was an avid supporter and adviser to Donald Trump and his campaign. His efforts seemed make him front-runner for a cabinet position. After Trump’s victory, Giuliani was noticeably absent from Trump’s cabinet. As earlier mentioned, his company had come under scrutiny for dubious international dealings. Many saw his $400,000 asking fee per speech as unsavory.  It was determined that Rudy’s history would set off Senate watchdogs and no one wanted more headlines.

Personal Legal Defense Team

The outspoken Giuliani finally landed a position with President Trump’s personal legal team in April 2018. Giuliani has known Trump since the 1980’s when Trump was flashing his faux glitter all around New York and New Jersey. Giuliani stated he was working for free. The offer to work for “free” reminded me of Paul Manafort’s offer to work for free as Trump’s campaign chairman. And we all saw how that turned out.

Don’t Let Truth Get In The Way

Once on Trump’s legal team Rudy Giuliani hit the airwaves hard and heavy.  His first goal appeared to focus on confusing the public.  The second goal was to discredit The Mueller Investigation and anyone involved with it.  During this time, Rudy Giuliani  would often contradict White House statements. One of the biggest such contradictions came when Giuliani confirmed that the President knew that Michael Cohen had made hush money payments to Stormy Daniels and another woman. Giuliani’s love of manipulating facts created confusion and fatigue.

Meet The Press

“As Trump’s personal lawyer, Rudy Giuliani gave cable-TV interviews sprinkled with contradictions that have often left viewers baffled.” Chuck Todd moderator for Meet The Press asked Giuliani why Trump was refusing to be interviewed by the Special Counsel. Giuliani said the president risked falling into a perjury trap, even if he told the truth.”  In an exchange that may go down as one of the Trump era’s most memorable, Todd responded, “Truth is truth.” To which Giuliani replied “Truth isn’t truth”(Bloomberg, Where does Rudy Giuliani money come from, 4/05/2019)

“I Don’t Peddle Influence”

Is Rudy Giuliani a lobbyist for the Trump administration

Is Rudy Giuliani acting as a lobbyist for the Trump administration or just a free agent

The question of conflict of interest is an important question when talking about Rudy Giuliani. The combative former mayor denies lobbying.  However,  he does materialize in world capitals where he makes statements “that dovetail with known Trump foreign policy positions.” (Bloomberg 5/04/2019).  Some critics claim that he is actually a “go between” for Trump and foreign leaders and is participating in illegal lobbying. He vehemently slaps aside such accusations.


Rudy Giuliani is both icon and clown. He has managed to dodge and dance around criticism and is without a doubt a successful businessmen. Despite his marital scandals, his conflicts of interest, his headline seeking behavior he is fighting a daily battle to remain a relevant figure in both business and politics. Many observers condemn his constant reminders of his of 9/11 “heroism.” Many in fact find his constant reliving of those dark hours in New York city history as  appalling.

Looking For Dirt

Over the last couple days, Rudy Giuliani has been making the rounds of cable news shows. Rudy Giuliani has told anyone that will listen that he is headed to the Ukraine.  He has stated that the Ukraine government has evidence of “dirt” on Joe Biden and Joe’s son, Hunter Biden.  He has stated he intends to “expose it.” Questions about the legality and morality of involving a foreign government into an upcoming presidential campaign ignited a firestorm from everyone except the Trump Republicans.

Foreign Interference

Looking for “dirt” on an opponent in the Ukraine. And bragging about it on national television. You have got to be kidding me. Apparently, Rudy Giuliani feels comfortable in involving a foreign government in another American election.  I for one do not think its okay. It looks to me as if Rudy has sold his soul for a couple of Trump golf cart rides.


Rudy Giuliani claims no corrupt intent. His stated intention is to investigate matters connected to the Mueller Report. His retort to the incredulous observer goes like this, ” We’re not meddling in an election. We are meddling in an investigation. Which we have every right to do.” This is a bridge too far.


Vladimir Putin is threatening the Ukraine

Vladimir Putin is threatening the sovereign nation of the Ukraine on a daily basis

The Russian Federation is an ongoing threat to the Ukraine on a daily basis.  I believe the Ukrainians will do, or say most anything, to get an American president to provide military protection from the Russian Federation. Soon after the announcement of his planned trip, Giuliani retreated from the plan. Saying, mysteriously, that he suspected he was being manipulated and drawn into a “trap.”  It sounds like a trap of his own making.

How Low Can He Go

Any acts of heroism Rudy Giuliani may have displayed on that September morning so long ago is becoming a smaller and smaller part of who he is. It is becoming more and more evident that one moment of cool headedness does not a hero make. The extramarital affairs, the lies, the conflicts of interest, the bigotry, the seedy clients, and his greed are what we will remember.  A sad legacy for a man who touched greatness, if even for only a moment.




Mayor of the World’- Person of the Year 2001 Time Magazine

Rudy Giuliani-Rudy Giuliani Wealth: Where Trump Lawyer’s Money Comes From-Bloomberg 4/05/19




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