Sunday, February 3 at 9 p.m. ET

Hosted E.D. Donahey

As a young prosecutor, he brought down the toughest mob bosses in New York. As mayor, he brought life back to a city on the ropes. And on September 11, he brought comfort to a nation under attack.

Don't miss our intimate portrait of the outgoing Mayor of New York, a man who's been dubbed "America's Churchill," Rudolph Giuliani.

Here's just some of what you'll learn about one of the most fascinating politicians ever to lead New York City.

Making the Man

Rudolph Giuliani grew up in Brooklyn, where he became a lifelong New York Yankees fan and where his parents owned a bar and grill. He attended catholic schools and once thought of becoming a priest. Could his roots explain the courage he would later need on September 11?

The Legal Eagle

In his junior year at Manhattan College, Giuliani decided to become an attorney. He worked as a law clerk for five years and became an Assistant U.S. Attorney in the Southern District of New York. The mayor credits the time he spent on the job with helping him develop his cross examination skills.

Later, he would leave New York to serve as an assistant to the Deputy Attorney General. It was during his tenure in Washington that he switched his party affiliation from Democrat to Republican.


Giuliani has managed to succeed as a politician despite breaking many of the cardinal rules of politics. Yet, he hasn't always managed to win in the political ring. We'll examine his failed bid for mayor in 1989, his curious endorsement of Democrat Mario Cuomo for governor instead of his Republican challenger and his aborted Senate campaign against Hillary Clinton in 2000.

We'll also tell you about his triumphs...how the mayor managed to cut crime by 50 percent, slash welfare rolls by nearly 500,000 people and how he led a city-wide renaissance of New York that led many to believe him when he proclaimed it "the capital of the world."

The Tough Guy

Where does Giuliani's "tough guy" image come from? And how has he sustained it and kept it alive? We'll look at some of his most controversial pronouncements on everyone from Atlanta Braves' ball player John Rocker to Yassir Arafat.

Tough Times

What's gotten the mayor through the tough times, when immigrant Amadou Diallo was shot 41 times by NYPD cops, his first defeat for mayor and the flap over a controversial art exhibit at the Brooklyn Museum which featured a portrait of the Madonna partially made out of cow dung? We'll show you what has helped guide him through adversity.

Wacky Rudy

At times Giuliani has been dubbed a "humorless autocrat" but the mayor has his silly side too. You won't believe some of this footage and we guarantee you'll be laughing!

The Passionate Politician

Any New Yorker who has watched the mayor in action during the past eight years can have no doubt that his is a man who loves his job. But Giuliani's enthusiasm doesn't stop once he leaves the office. He's not only passionate about his job...he loves a lot of life. From opera to cigars, to the Civil War and of course, his beloved baseball team, the New York Yankees, Giuliani's zest for life has been described by many of his friends as his most charming trait. Meet some of the people who tell us what it is like to share some of their passions with the mayor.