A fully unleashed Rudolph Giuliani, free of electoral concerns and financial worries, has relentlessly criticized President Barack Obama in recent weeks, questioning the commander in chief's love of country while placing the blame for much of society's ills at the front door of the White House.
But those same inflammatory views that have been eaten up by some conservatives are significantly out of step with the prevailing political views of liberal New York City. And experts suggest they could further muddle Giuliani's complicated legacy in the city he led for eight years, including in its darkest hours.
"Giuliani has gotten more brazen in his rhetoric but his target audience is now the far right," said Jamie Chandler, a political science professor at the City University of New York. "He's no longer interested in wide appeal."
Always outspoken, Giuliani's transformation from moderate Republican mayor of an overwhelmingly Democratic city to right-wing hero — one that first accelerated during his ill-fated 2008 presidential bid — was arguably never more apparent than last month when he took the stage at a fundraising dinner in Manhattan to benefit likely GOP presidential candidate Gov. Scott Walker of Wisconsin.
"I do not believe, and I know this is a horrible thing to say, but I do not believe that the president loves America," said Giuliani, who arrived unannounced and was unaware there were reporters in the room. "He doesn't love you. And he doesn't love me. He wasn't brought up the way you were brought up and I was brought up through love of this country."
Giuliani — who, in a less publicized outburst, shouted "Mr. President, wake up. Come off the golf course" at an Arizona speaking event the week prior — did not back off his remarks even after they created a firestorm, dominating headlines nationally for days.
Last week, Giuliani appeared on a New York radio show and suggested that Obama should be held responsible for disturbing events ranging from the violence that erupted in Ferguson, Missouri, after a police officer was not charged for shooting an unarmed man to a teenage brawl at a Brooklyn McDonald's.
"It all starts at the top. It's the tone that's set by the president," the ex-mayor said.
Giuliani's incendiary comments angered many in the city he still calls home, including the current occupant of City Hall.
"I find it a cheap political trick for Rudy Giuliani to question our president's love of his country," said Mayor Bill de Blasio, a Democrat, the day after Giuliani's remarks at the Walker fundraiser. "That is stooping very, very low, even for him."
Repeated requests for an interview with Giuliani were declined and a spokeswoman for the former mayor said Giuliani will spend the rest of March traveling overseas.
Giuliani, a former U.S. Attorney, was elected mayor in 1993 on a pledge to slash the city's sky-high crime rate. That year, 1,946 people were murdered in the city. In 2001, Giuliani's final year in office, that number shrank to 649.
Giuliani was largely praised for the drop in crime but remained a divisive figure. His no-holds-barred defense of the New York Police Department, often at the expense of minority communities, drew sharp criticism. A possible Senate run was abandoned due to a cancer diagnosis. And after years of public battles and a very messy public separation from his wife — which resulted in him moving out of Gracie Mansion, the mayor's official residence — his poll numbers sunk and many New Yorkers were eager for a change at City Hall.
But then, one clear September day just a few months before he was to leave office, two planes flew into the World Trade Center.
In the hours after the attacks, with President George W. Bush largely unseen, Giuliani became the face of the nation's grief. His leadership — both inspiring and compassionate — over the following weeks was widely lauded, earning him the nickname of "America's Mayor."
But his relationship with the city would soon change again.
Giuliani played a key role in the 2004 Republican National Convention, held at Madison Square Garden, which re-nominated Bush, a deeply unpopular figure in New York. And he shifted right on a number of issues — including gun control and public funding of abortions — during his failed run for president four years later.
Though his future electoral prospects vanished, he remained a conservative darling, a frequent guest on Fox News and a sought-after member of the political speaking circuit. He is a partner in a law firm and his consulting firm, Giuliani Partners, has significant international business. In 2007, the last time Giuliani disclosed his assets, he reported a wealth of more than $30 million.
Now, he appears motivated by a need to stay relevant within the Republican Party and to keep driving clients to his business. But it's also not just Giuliani who has changed since he left office.
Thanks to wave of new arrivals (in part drawn to the drop in crime he helped create), New York has become a younger, more diverse and more liberal city. Meanwhile, much of Giuliani's former political base — older, conservative, ethnic white voters — have either moved away or died.
A pair of 2013 polls starkly displayed New York's complex feelings for Giuliani. In one, Giuliani was named the city's most successful mayor of the last 50 years. In another, a vast majority of voters said they would not vote for any candidate Giuliani endorsed.
That fall, the GOP candidate Joe Lhota, a former Giuliani deputy mayor, was routed by de Blasio. Giuliani was only used sparingly on the campaign trail.
Some pundits feel that Giuliani's recent comments have cemented his dual legacy — while he could not be elected today, his performance after September 11 will always be honored.
"His current behavior brings back memories of Giuliani being a polarizing and racially divisive figure," said Kenneth Sherrill, political science professor emeritus at Hunter College. "That is why it was so remarkable that he became such a unifying figure after 9/11. I think he'll be remembered for both the good and the bad."
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