Rudy Giuliani, America’s Mayor, is back in the spotlight working as President Trump’s

personal attorney.

Donald Trump and Rudy Giuliani have one major trait in common

I think their styles are very similar

That’s Shannon Pettypiece.

Within 48 hours, Giuliani went on an all-out media blitz.

PETTYPIECE: He started contradicting himself quite quickly

GIULIANI: Having something to do with paying some Stormy Daniels woman $130,000, which

is gonna turn out to be perfectly legal.

That money was not campaign money.

Sorry, I’m giving you a fact now that you don’t know.

That’s Andrew Kirtzman, who literally wrote the book on Giuliani.

GIULIANI: Funneled through a law firm, and the president repaid it.

HANNITY: Oh, I didn’t know -- he did?

There’s no campaign finance law.

GIULIANI: Zero.

Pettypiece: And I think it was less than 48 hours later had to put out a statement trying

to clarify what he was saying, because his comments had created even more confusion.

So while Giuliani’s tenure got off to a rocky start, why did Trump even pick him to

be his lawyer in the first place?

Pettypiece: While Giuliani has a lot of experience with the Justice Department there were a number

of lawyers who were more suited to deal with the type of investigation like this, who basically

turned the President down because of conflicts or concerns about what would happen to their

reputation for working for this controversial president.

So then what does Giuliani actually bring to the table?

Kirtzman: Giuliani was brought on as much to be Trump’s lawyer as to be Trump’s

confidant.

Pettypiece: He is someone that the President trusts and that can communicate with the President

in a clear, straight way that he'll understand..

And this trust comes from decades of Trump and Giuliani running in New York circles.

Pettypiece: When Giuliani was with the Justice Department in New York, he was there as a

very high-profile prosecutor and Donald Trump was in New York as a very high-profile businessman

and real estate developer.

They both inhabited the same world.

That world was New York City in the 70s and 80s.

In 1983 Giuliani became the Manhattan U.S. Attorney who took on the mob.

And he did so in an extremely public way, holding press conference after press conference,

in what was up until that point, a very press-shy job.

Pettypiece: He was the type of prosecutor who was on the cover of newspapers and the

cover of magazines

On November 20th, 1986, Giuliani won the conviction of all eight defendants in the massive mafia

commission trial.

And then…in 1993, he became the first Republican mayor of New York since 1965.

He ran on the platform of reducing crime, and he delivered.

In the early 90’s New York was crime-ridden with a dwindling middle class.

By the millenium, violent crime in the city dropped 56 percent.

However, by the end of his second term, his polls were lagging, and his legacy was about

to be “the mayor who cleaned up New York City”, but then…

“So this looks like it is some sort of concerted effort to attack the World Trade Center.”

Pettypiece: And that's when he moved from being Daily News, New York Post cover famous,

to being a famous figure across America.

OPRAH: He’s the mayor of New York City -- Rudy Giuliani!

Kirtzman: He was time magazine’s person of the year, he was a natural presidential

contender.

So he decided to run for president.

GIULIANI: I believe we can hand our nation to the next generation, better than it was

handed to us.

And the GOP nomination was there for the taking.

Kirtzman: He was far and away more popular, and also better known than his republican

competitors as a result of 9/11.

But he made some catastrophic campaign decisions.

And there was also his 9/11 problem...

TOM BROKAW: Joe Biden had one of the best lines of the campaign when he said...

JOE BIDEN: Rudy Giuliani, there’s only three things he mentions in a sentence: A noun,

a verb, and 9/11.

I mean, there’s nothing else.

Giuliani’s poll numbers plummeted, and he didn’t secure a single state for the GOP

nomination.

Kirtzman: His political career was wrecked.

. And so he went back into kind of private practice, but basically, he was out of action.

But in 2016, an opportunity.

Giuliani: But what I did for New York, Donald Trump will do for America!

Giuliani hitched his wagon to the Trump train, and while he was passed over for multiple

cabinet positions when Trump became president, being appointed as Trump’s council has thrust

him back into the spotlight.

But no matter what may happen from here, it probably won’t really affect his true legacy...

Pettypiece: I think the most memorable image of him will always be in America's minds on

those days after 911.

Kirtzman: He’s a person who took on the mob and had extraordinary results, and then

turned around New York City, and then led America through its worst crisis.

Those are accomplishments of a lifetime.