Former New York mayor Rudy Giuliani. (J. Scott Applewhite/Associated Press)

If you've been paying attention to the presidential race over the past two months or so, you'll notice that Rudy Giuliani has repeatedly been willing to say things about Democratic presidential nominee Hillary Clinton that no one else would -- not even Donald Trump.

The former New York mayor's latest hit on Clinton came earlier this week when he offered a bit of post-debate advice to Trump. Here's an excerpt from an interview with Elite Daily:

I sure would’ve talked about what she did to Monica Lewinsky — what that woman standing there did to Monica Lewinsky, trying to paint her as an insane young woman when, in fact, Monica Lewinsky was an intern. ... And after being married to Bill Clinton for 20 years, if you didn’t know the moment Monica Lewinsky said that Bill Clinton violated her, that she was telling the truth, then you’re too stupid to be president.

Pretty strong stuff, right? But that sort of harsh  -- and personal -- rhetoric is more the rule than the exception for Giuliani of late.

Think back to his rousing speech at the Republican National Convention, the speech that gave us this Top 10 GIF of the 2016 campaign:

In that address, Giuliani savaged Hillary Clinton for her alleged "dereliction of duty" during the attacks in Benghazi, Libya, in September 2012 when she was secretary of state. Here's a longer excerpt of that riff:

Her dereliction of duty and failure to keep her people safe played a major role in the horrific Islamic terrorist murders on September 11-12, 2012, in Benghazi which claimed the lives of four brave Americans; our ambassador J. Christopher Stevens, U.S. Foreign Service officer Sean Smith, and CIA agents Tyrone S. Woods and Glen Doherty.

And Clinton, and the Obama administration, for political reasons lied about the purpose of the attacks including her lying directly to the families of those who were killed.

Hillary Clinton’s answer to Congress about the death of these four brave Americans because of her failures as secretary of state was “What difference at this point does it make?"


At the end of last month, Giuliani was leading the charge that Clinton's health was shaky. "Go online and put down 'Hillary Clinton illness,' take a look at the videos yourself," he urged the media during an appearance on Fox News Channel. "She'll give a speech on a teleprompter, and then she'll disappear. I don't know if she goes home [and] goes to sleep. I think she sleeps.” Giuliani offered no evidence of his claim other than that Clinton "looks sick."

The fervor that Giuliani has taken to the attack over the past few months has even surprised -- and unsettled -- some Trump confidantes. Check out this tweet from the New York Times's Maggie Haberman Wednesday morning:

What's most fascinating to me in all of this is that as recently as eight years ago, Giuliani was seen as a force for moderation in the Republican Party. His 2008 presidential campaign was predicated on the idea that a sustainable center existed within the GOP and that he could unite it. Today he is operating at or very near the fringe of the party in terms of the ideas about Clinton he is willing to embrace. And, he is doing it all loudly and angrily.

I reached out to numerous current and former Giuliani confidants to get some perspective on why he has taken a turn for the radical in this race. None of them responded. Draw your own conclusions there.

My sense is that Giuliani's fervor is mostly explained by his truncated 2000 Senate campaign against Clinton. That was expected to be a race for the ages -- a massively expensive contest between two people who knew each other well and really didn't like each other. Giuliani dropped out of that race in its very early days following a prostate cancer diagnosis. Since then, Clinton has served in the Senate and as secretary of state and is now the Democratic presidential nominee. Giuliani has only a never-got-started presidential bid under his belt in the days since that race.

It looks and feels as though Giuliani is running the race he wishes he could have run against Clinton 16 years ago. But it's more than that. It's that and the fact that he has built up a decade and a half's worth of resentment (or, maybe, more resentment) about Clinton and what he thinks she will do to the country if elected.

Is any of Giuliani's rhetoric actually effective? My guess is it's not, because Giuliani is, largely, preaching to the choir when he calls Clinton stupid or questions her health. But I am not totally sure Giuliani cares whether his attacks work. This is deeply personal to him. And boy, oh boy, can you tell.