Can Bloomberg Win? Rudy Had It Easier When He Ran in ’93

Michael Bloomberg, surrounded by sharply dressed advisers, strode into a small restaurant on Third Avenue in Bay Ridge on the afternoon of June 7. The billionaire media mogul and Republican Mayoral candidate had ventured into the heart of Giuliani country in search of the outer-borough, white-ethnic New Yorkers who overwhelmingly supported Mayor Rudolph Giuliani in 1993.

Dressed in a dark suit and tasseled shoes, Mr. Bloomberg paused to linger over a table where Rick Carpenito, a 31-year-old Verizon technician, was finishing a plate of ziti with a friend.

After a bit of banter, Mr. Bloomberg said: “The other day, we were filming an ad and a guy said to me, ‘Give me a dollar and I’ll vote for you.'”

Mr. Carpenito eyed Mr. Bloomberg for a moment and said: “Give me half a million–I’ll vote for you.”

Half a million dollars per vote could prove too steep even for Mr. Bloomberg, whose estimated worth is $4 billion. Indeed, as his afternoon campaigning in Bay Ridge showed, Mr. Bloomberg faces two huge obstacles as he seeks to succeed Mr. Giuliani: He isn’t Rudy Giuliani. And he isn’t running against David Dinkins.

The conditions that enabled Mr. Giuliani to gain City Hall as a Republican in an overwhelmingly Democratic city just don’t exist this time around. Mr. Giuliani won because swing Democratic voters–upper-middle-class Manhattanites as well as moderate, outer-borough Catholic and Jewish Democrats–were terrified by the crime and disorder that marked the Dinkins years. He won because Staten Islanders–prototypical Giuliani supporters–flocked to the polls in high numbers not simply to support the Republican, but also to cast “yes” votes on a borough-wide (but non-binding) referendum to secede from the city. He won because he’d spent four years intensely studying the issues after his loss to Mr. Dinkins in 1989–making him, in the end, a more impressive candidate than his opponent. And despite all this, Mr. Giuliani won by a mere 50,000 votes–a couple of percentage points.

None of these conditions exists for Mr. Bloomberg, who still has to win the Republican primary before he can think about the general election. There will be no mortally wounded incumbent like Mr. Dinkins to run against; there is no reason to anticipate a huge turnout in Staten Island or any other area of strong Giuliani support; and, if Mr. Bloomberg’s first several weeks of campaigning are any guide, he has little of the grasp of issues Mr. Giuliani displayed in 1993. Although Mr. Bloomberg gave an education speech on June 11, he has declined to answer almost all questions about his specific stances on issues.

“If Giuliani, who was very well prepared, could only win by 50,000 votes after the disasters of the Dinkins years,” said Fred Siegel, a senior fellow at the Progressive Policy Institute, “then why do we suppose that, in the midst of peace and prosperity, we’re going to elect a previously unknown billionaire who just seems to be dabbling in politics?”

Unlike Mr. Giuliani, who was well-known from his days as a U.S. Attorney and his failed Mayoral run in 1989, Mr. Bloomberg is barely known to voters and has fewer than six months to introduce himself.

“Is this him?” one Bay Ridge woman asked outside a campaign event as she pointed to New York Times reporter Adam Nagourney.

Mr. Bloomberg may also have some trouble connecting with the middle-class white Catholics he’s likely to need to offset the support his eventual Democratic opponent will enjoy among independent-minded liberals in Manhattan and neighborhoods such as Park Slope in Brooklyn and Riverdale in the Bronx. Mr. Giuliani, the son of a tavern-keeper and the product of a Catholic-school education, can come across as one of them. Mr. Bloomberg, a bookkeeper’s son who socializes on the Manhattan party circuit, looked like he had strayed onto alien territory when he mixed with the locals in Brooklyn.

At one point during his heart-of-New-York swing, Mr. Bloomberg walked into a pizzeria on Third Avenue surrounded by aides and reporters. As cameras flashed, Mr. Bloomberg, who zealously watches his waistline, was offered a slice.

“The smallest slice you have–with cracked red pepper on top,” Mr. Bloomberg replied.

Several moments later, he took up a place behind the counter, where he tried his hand at the storied local craft of pizza-making. Standing next to an apron-clad counterman with tattooed forearms the size of tree trunks, Mr. Bloomberg repeatedly tossed a clump of pizza dough approximately six inches into the air. Meanwhile, off to the side, a tall, young campaign aide perched on high heels laughed, clapped her hands and shouted: “Higher! Higher!”

Mr. Bloomberg’s advisers dismiss the notion that his unsteady start bodes ill for the campaign. “If people want someone who’s really good at glad-handing, then Mike’s not their guy,” said Bill Cunningham, a senior adviser to Mr. Bloomberg. “But if they want someone to talk about the problems facing the city in coming years and to provide ideas, then Mike is their guy.”

Mr. Bloomberg’s advisers say that eight years of Mr. Giuliani have transformed the electoral landscape, creating an entirely different set of circumstances from the ones that made Mr. Giuliani’s rise to power possible. In this view, the old equation–in which the New York electorate chooses a Republican once a generation and then promptly reelects a Democrat–has been shattered by Mr. Giuliani.

“[The public] will have a very clear distinction between Mike and the rest of the field,” Mr. Cunningham said. “It is that distinction that will motivate voters–not some idea that voters must go back to the Democrats because that is the natural order of things.”

As it happens, however, some of the demographic shifts in the city in recent years may turn out to favor Democrats. “The city is more Democratic now than it was eight years ago,” Mr. Siegel said. “Huge immigration and a rise in the young, single population are the two big changes–and both groups are strongly Democratic.”

What’s more, the get-out-the-vote operations run by the city’s municipal unions are energized after playing key roles in the victorious campaigns of Senators Charles Schumer in 1998 and Hillary Clinton in 2000. Mr. Bloomberg runs a non-union shop and will be the candidate least likely to give the unions a good deal come contract time (“If I had my druthers, I’d lock them in a room, put them on a starvation diet, or hunger strike until they come up with a solution,” Mr. Bloomberg recently said of contract negotiations between City Hall and the teachers’ union). So it’s likely that the unions will be cranking as hard as possible to ensure that the Democratic nominee defeats Mr. Bloomberg in the general election in November.

Mr. Bloomberg well knows that the unions will be arrayed against him. Nor is it clear that Mr. Bloomberg has what it takes as a candidate to shatter the old formula, in which the city reverts to Democratic control after a Republican Mayor has cleaned house. Well before he declared his candidacy–via a television ad–his advisers were concerned that Mr. Bloomberg’s image as a billionaire playboy could hamper his ability to reach everyday voters. As The Observer reported on March 12, his pollster, Frank Luntz, convened focus groups to test-market various responses to the inevitable questions he is facing about his wealth. The participants watched a videotape of Mr. Bloomberg in which he was asked if he thought New Yorkers would elect a businessman Mayor. In response, Mr. Bloomberg discussed his modest background, his hard-working father and his early struggles to make money.

In the meantime, Mr. Bloomberg certainly isn’t playing the part of a modest newcomer to New York politics. After he gave his June 11 education speech at the Waldorf-Astoria Hotel, Mr. Bloomberg made the rounds of the ballroom with Luis Melendez, an 11-year-old Trinity Middle School student. As he approached the press table–all of four journalists thick–he paused.

“Look, Luis,” Mr. Bloomberg said. “The people at this table, judging by the way they’re dressed, are journalists. If you don’t get an education, you might end up like them.”

At that, one of the reporters jumped up and asked Mr. Bloomberg why he was running for Mayor.

“I want to change the world,” he answered.

“But why can’t you do that as a businessman?”

Mr. Bloomberg paused. A camera flashed in his face.

“I’ve already done that,” he said, and backed away from the table.

–Additional reporting by Petra Bartosiewicz Can Bloomberg Win? Rudy Had It Easier When He Ran in ’93