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A Dead End Job No More?
Giuliani and Bloomberg look to escape the Curse of Gracie Mansion

By Edward-Isaac Dovere

Political circles are abuzz these days with speculation that either Rudolph Giuliani or Michael Bloomberg—or both—will join the 2008 presidential race. There is every reason to believe each could be formidable, and perhaps even successful.

Except, that is, for a fact of political history that has undercut every New York City mayor with higher ambitions for the last 140 years. King Tut and Tecumseh have actually killed people with their curses, but when it comes to political careers, little has been more universally deadly than a stay in Gracie Mansion.

Going into the race, both the former and current Republican mayors have strong hands to play. Giuliani was spectacularly successful in fighting crime, and helped usher in a rebirth of the city during the 1990s. Bloomberg has proven impervious to most political manipulation, adeptly transferring his corporate management style to the city and helping lead its resurgence following the Sept. 11 attacks. Both were overwhelmingly reelected as mayor.

No Way Up
Though only two have ever moved on politically, New York’s mayors have traditionally been mentioned as possible candidates for higher office. But what sells in the Big Apple seems to sell only in the Big Apple, as every recent mayor who has tried to move on has quickly discovered.

“The schmaltziness of Ed Koch worked in New York, the feistiness of Fiorello LaGuardia worked in New York,” said veteran GOP consultant Roger Stone, Jr. “Middle America doesn’t quite understand the milieu.”

With the exception of the scandal-rocked term of William O’Dwyer, which was completed by Vincent Impellitteri, here are some recent mayors who have been in contention for higher office, and some who have not:

Fiorello LaGuardia
The “Little Flower” began his three terms with a national radio address promising to “guard and protect and guide” the return of the city to the people after the scandal-rocked years of his predecessors, Jimmy Walker and John O’Brien.
He won the mayor’s race on his second try, and oversaw a successful tenure as the country struggled with the Great Depression. He was often talked about as a potential vice presidential candidate, and many believe he opted not to run for a fourth term in 1945 to try to lay the groundwork for a national run. But the chance never came before he died from pancreatic cancer in 1947.
“We were a showcase for the New Deal because LaGuardia made it work,” explained conservative commentator Fred Siegel. “Even so he wasn’t a national player, which frustrated him enormously.”

Robert F. Wagner, Jr.
Wagner’s father, Robert F. Wagner, Sr., served more than 20 years in the Senate, introducing major pieces of New Deal legislation, including the establishment of Social Security. Wagner began his own political career in the Assembly, and after a taking break to serve in the Air Force during World War II, was the commissioner of various agencies under Mayor William O’Dwyer. In 1956, he was nominated by Democrats both for the vice presidency and for senator from New York, but lost both.

After three terms as mayor, he spent a year as ambassador to Spain, before trying unsuccessfully for a fourth term as mayor in 1969. President James Carter later appointed him the first American representative to John Paul II in 1978.

John Lindsay
By 1972, the man whose good looks earned him comparisons to the Kennedys had completed his metamorphosis into a Democratic candidate for president. He entered the Florida and Wisconsin primaries, and got seven percent of the vote in each, dropping out in April.

He did not seek a third term in Gracie Mansion, and after losing the 1980 Democratic primary for Senate to Liz Holtzman, spent the last 30 years of his life in private life and practice.

Abe Beame
Fiscal troubles put the city in bad shape for much of the four years that Beame was in office, and he was ultimately defeated in the 1977 Democratic primary. He never ran for anything else, spending the rest of his life as a chairman and senior advisor to banks.

Ed Koch
Koch was elected to a second term in 1981, and the next year made a bid for governor in what shaped up to be a rematch against Mario Cuomo. Koch’s comments slamming upstate residents hurt him, and he lost to Cuomo.

“I was happy I lost,” Koch said. “I didn’t really want to leave New York City. I did it out of hubris, when I decided to run. I didn’t want it, but I just wanted to sort of take another scalp, and God said no.”

David Dinkins
His term was beset by troubles and controversy, and he lost his 1993 rematch to Giuliani. He left politics as a career, but now teaches it at Columbia’s School of International and Public Affairs. He remains an active member of the “Gang of Four” powerful Harlem Democrats with former Manhattan Borough President Percy Sutton, former State Sen. Basil Paterson and Rep. Charles Rangel.

By Edward-Isaac Dovere

They also hold potential trump cards. Giuliani became “America’s mayor” as he shepherded the city through the World Trade Center’s destruction and its immediate aftermath, and has continued to be one of the nation’s most popular political figures. Bloomberg’s is a multi-billion dollar fortune that already enabled his 2001 and 2005 campaigns to be the best-funded runs for mayor anywhere. He has publicly toyed with spending upwards of $500 million on a White House drive.

“Saying ‘What would Giuliani be like without Sept. 11?’ is like saying ‘What kind of player would Barry Bonds be if he didn’t hit home runs?’ Who cares?” said Republican strategist Kieran Mahoney. He advised all three campaigns of Gov. George Pataki, Sen. Alfonse D’Amato’s 1992 reelection bid and Kansas Sen. Robert Dole’s 1996 quest for the White House.

And given the cost of the independent run Bloomberg would likely have to make, Mahoney said, “I don’t know if the analysis of what a Bloomberg candidacy would be like without the money is worth starting.”

Most political analysts agree that after two terms of the Bush presidency, voters will be most concerned with competence as they pick their next president. The urban renaissances that Giuliani and Bloomberg each oversaw as mayor will therefore give them incredibly strong foundations for candidacies, should they declare them.

“Both of them would be able to plausibly argue that they ran a large, very complex government in a very able and successful fashion that prepared them for the basic task of running a large government,” said Mahoney, the GOP consultant.

But they will need a lot more to make it out of the gate, Mahoney argued.

“Failure to make that argument disqualifies you from consideration,” he said. “But making that argument doesn’t get you elected.”

They will also have to deal with the realities that have tripped up their predecessors. Whether because of individualized electoral idiosyncrasies or some supernatural hex, the last mayor of the city to go on to any other elected office was John Hoffman, elected governor in 1868. Despite all the ambitions and all the egos of the men who have led New York City, Hoffman and DeWitt Clinton before him—both of whom became governor—are the only two New York mayors who have ever moved on after being mayor. And both did so decades before the consolidation of the five boroughs.

Not for lack of trying.

“They generally lose,” explained 1982 gubernatorial candidate and former Mayor Ed Koch (D), because constituents rarely see their mayors in the same light as their other chief executives.

“As I always used to say, if you don’t like what the president is doing, 400 bucks, you go down round-trip to Washington. You don’t like the governor? 200 bucks, round-trip to Albany. You don’t like me? Three dollars, come on down,” he said. “And they came.”

That, and the constant public assault of every urban gripe for which the mayor is personally given the blame, are liabilities for mayors everywhere, Koch said. “It’s everywhere the same, it’s just magnified in New York,” he said.

But election results from elsewhere around the country indicate otherwise. Mayors of other cities have gone on to Congress, attorney general, and state comptroller. James McGreevey (D) was mayor of Woodbridge before becoming governor of New Jersey. California’s Dianne Feinstein (D), who was San Francisco’s mayor, and Minnesota’s Norm Coleman (R), who was St. Paul’s mayor, are just two of the current United States senators whose political résumés include leading a city hall.

“The job itself is limiting in terms of your political future because of the hard decisions you have to make.” — veteran Republican operative Roger Stone, Jr.

And then there is a certain former mayor of Peekskill who, after 10 years split between the houses of the state legislature, began a three-term stint as governor, now entering its final days.

So what is wrong with New York’s mayors? Most of them have quickly, and often spectacularly, climbed the city’s political ladder. Many have held several other offices before getting to run City Hall, gaining experience and political acumen along the way.

This has served them well with the city electorate: of the last 10 mayors, three were elected to three terms, and three others to two terms (and given public sentiment after Sept. 11, had Giuliani not been up against his term limits, he may very well have been in the first group, rather than the second). Mayors have come out of Congress, not gone to it.

They have so effectively established the job in the popular psyche as the second hardest in America—and, some say, the second-highest profile—that other political offices no longer seem clear steps up in a political career.

“I think to be mayor of New York is in several key ways much more difficult than being senator or governor,” said Bob Kerrey, who was elected to both offices by Nebraskans in the 1980s and 1990s, with a 1992 presidential candidacy along the way.

Kerrey, who came to the city to head the New School after leaving the Senate, briefly considered entering last year’s mayor’s race. Actually running would have been impractical, he said, but the allure of the job has kept the dream alive in his mind.

“If I knew the city better and had a stronger foundation of close associates and friends, the answer would be yes,” Kerrey said. “There’s something about being mayor of New York.”

Kerrey is not the only national figure who has flirted with the job. In the closing months of his presidency, after his wife won her Senate seat from their new home, Bill Clinton (D) was dismissing rumors that he would jump in to the 2001 race. With Marist College poll at the time showing 44 percent of city residents backing the idea of him running, Clinton was asked in November of 2000 whether he would run.

“Not anytime soon,” he said, a phrasing that many people thought may still prove to be only a temporary dismissal.

Between Al Smith and the Roosevelts, New Yorkers dominated national tickets for the first part of the 20th Century. The last major party presidential candidate from New York was Thomas Dewey, who leapt straight from Manhattan district attorney to three terms as governor before making his 1944 and 1948 presidential runs.

“If you can make it here, you can make it anywhere,” goes the song.

But Frank Sinatra was not singing about politics.

New York mayors have administered the city’s complexities, balancing interest groups and unions, making sure the trash gets picked up and the trains run, all while dealing with the scrutiny that comes from leading the media capital of the world.

The city budget, clocking in at $53 billion, is larger than any government’s in America besides the federal budget and the state budgets of New York and California. The population of 8.5 million means that if the city were its own state, it would be the 12th most populous—four times the size of the population Clinton led during his six terms as Arkansas governor. Mayors are responsible for tending to the heart of a metropolitan area that is home to more than 20 million people—as many as George W. Bush was responsible for while governor of Texas. One in every 14 Americans is in some way dependant on the job the mayors do.

Because of the city’s size, just about every type of problem eventually crosses the desk of a mayor—including those created and amplified by the size itself, and that contributes to mayors’ political problems.

Bill Lynch, a deputy mayor under Mayor David Dinkins, remembers a time when Dinkins was talking about the AIDS epidemic, accompanied by a chart tracking total infections, separated by city. The line for New York was “twice as long,” Lynch recalled.

“Nobody took into consideration that New York was three times as big as most of those other cities,” Lynch said. That scared people.

When Dinkins hosted a conference of big city mayors, Lynch remembers the reactions as people were told that New York had more people living in public housing than the total hometown populations of many of their guests. That scared people, too. Lynch said this, and the country’s general love-hate relationship with New York City, is why mayors have struggled.

“If you can make it here, you can make it anywhere,” goes the song. But Frank Sinatra was not singing about politics.

That love-hate relationship is a high hurdle on its own. Few non-New Yorkers who cleave close to the city as an idea or temporary destination actually want to see it replicated closer to home. And that, analysts say, is why they keep mayors at arm’s length.

“The rest of the country and maybe upstate likes you from afar,” Koch explained. “I get great responses when I go upstate and when I go to other states, but I don’t know if they would like to live with me.”

Harold Ickes, the veteran Democratic operative who worked for Dinkins and in the Clinton White House, said this love-hate relationship gives New York City mayors “a special burden” which prevents frank consideration of their candidacies for higher office. Without it, Ickes said, the transition from New York mayor to president might seem a logical trajectory of executive experience, a factor often seen as key to winning a national campaign.

“If you think of the presidency in terms of managerial talent—a successful mayor of New York, it seems to me, that burnishes a big credential,” he said.

Moreover, Ickes said, mayors lack experience working with foreign policy, generally seen as a must for all future presidents in the post-Sept. 11 era.

“Maybe they can overcome that, but it would be a big problem,” Ickes said.

Then again, New York City mayors do tend to take stands on foreign affairs, even though this is not in their official job descriptions. Giuliani famously tossed the late Palestinian leader Yasser Arafat from a Lincoln Center concert and tried to strip diplomats of their immunity to parking laws. Bloomberg has recently lamented John Bolton’s resignation as United Nations ambassador and traveled the world in his failed attempt to boost the city’s 2012 Olympic bid. Not what most people would call diplomacy, true, but indications that the mayors of New York may not need inner tubes to swim in international waters.

The biggest obstacle for New York mayors on the political job market may be the very thing that often gets them talked about in the first place: juggling so many competing interests from the city’s myriad microcosmic communities often leaves mayors bruised and scarred.

That explains the traditionally low approval ratings of outgoing mayors, said Roger Stone, Jr., a veteran Republican operative who began his career volunteering for William F. Buckley’s 1965 mayoral campaign. He has since played various roles in the presidential campaigns of Richard Nixon, Ronald Reagan and George W. Bush.

The necessary compromises, Stone said, play even more poorly outside the five boroughs. Arguments and negotiations are rarely recounted with all their nuances, and the resulting stories rarely flatter the mayors.

“The job itself is limiting in terms of your political future because of the hard decisions you have to make,” Stone said.

New York’s political ideology does not make things any easier for mayors, Stone added.

“Views in New York in the mainstream, in the rest of the country are viewed as being in the extreme,” he said.

Moreover, though the mayoralty may be good training for higher offices, the politicking inherent to governing the city is not, said Fred Siegel, author of the Giuliani biography “Prince of the City” (soon out in paperback), and editor-in-chief of www.citiesonahill.org. Interest and ethnic group dynamics make for contentious political episodes during the process of governing, but with support amassed early behind selected candidates those dynamics rarely translate into competitive elections on any level in the city. Dealing with that, Siegal said, leaves mayors unprepared for dealing with larger electorates on the statewide or national levels.

“When you come out of New York, you’re not experienced in the rough-and-tumble of competitive elections,” Siegel said. “The language you speak is that of the one-party state.”

Unlike nearly every mayor who preceded them, Giuliani and Bloomberg have never held any elected office besides mayor. Historically, this is significant: 2008 will be the first national election since 1952 without an incumbent president or vice president running. That race was won by Dwight Eisenhower (R), the revered World War II general who had briefly been Columbia University’s president, and had been unsure of whether he was a Democrat or Republican only a few years earlier.

A similar national appetite two years from now could serve either Giuliani or Bloomberg well. Both are political iconoclasts: Giuliani is a hardliner on many issues, including security, but supports gay rights, abortion rights and gun control. Bloomberg is a Republican of convenience whose still liberal Democratic ideology is overlaid with a heavily pro-business pragmatism. Neither fits well into the existing political dichotomy, and certainly not into the national Republican Party of recent years.

Were Giuliani a Democrat, he could have been that party’s 2004 presidential nominee, or preparing to trounce his 2008 primary opposition. The same could be said of Bloomberg. In a political moment when a fiscally conservative, socially moderate population complains about partisanship, there is little question why the potential presidential candidacy of a centrist, fiscally conservative, socially moderate to liberal non-career politician has sparked interest. Add in Giuliani’s national hero status and Bloomberg’s billions attached to his own media empire, and it is not hard to see why those flames have been fanned.

They could do what Fiorello LaGuardia never got a chance to do, what Robert F. Wagner, Jr. dreamed of, and what John Lindsay in the 1972 Florida and Wisconsin Democratic primaries discovered he had no hope of doing.

There are many reasons to believe neither can win a presidential campaign, with Giuliani too liberal to get past Republican primary voters, and Bloomberg facing historically insurmountable odds for the independent candidacy he would almost certainly be forced to run.

But there is ample reason to believe that either one could win. They are national figures, with the modern media making them even more so in the general public’s eye than past mayors. They have the focus from Sept. 11 that continues to make voters nationwide identify more with New York than probably ever before. More and more Americans have positive personal experiences with the city, as tourists continue to flow through the streets in high numbers.

And if there actually is a curse, they have the facts on their side to overcome it. Just months before he became a national hero, Giuliani left Gracie Mansion to his wife and children in the midst of a messy divorce. Bloomberg, who owns an opulent townhouse on Manhattan’s Upper East Side, never lived there.

They abandoned Gracie Mansion, and perhaps the Curse of Gracie Mansion will abandon them.