The biggest dead-end job in politics

What do John Lindsay, Rudy Giuliani and Bill de Blasio have in common besides having been mayor of New York City? Hint: This will likely soon be true of Michael Bloomberg too.

All were failed presidential candidates. That’s probably not a coincidence, like the fact that Bill Clinton and Mike Huckabee were both born in Hope, Arkansas. Rather, it suggests that becoming mayor of New York City is the surest way to guarantee one will never be elected president. In fact, if recent history is any guide, New York City mayors stand no chance of winning any presidential primaries or statewide offices either.

Even Bloomberg’s billions are unlikely to overpower the gravitational pull of a record in City Hall. Like speaking at NYPD graduation ceremonies and marching in ethnic pride parades, it’s inherent to the office.

In each case, one can point to specific flaws in the candidate’s political profile: These men haven’t all exuded charisma, lived the cleanest lives – or even been considered successful mayors. “I don’t think New York has been putting its best foot forward,” as Kenneth T. Jackson, the Columbia University historian and editor of The Encyclopedia of New York City, ruefully put it. “I think Mike Bloomberg’s easily the best mayor New York has ever had, so (his campaign) will be interesting to watch.”

The history of political careers ending at city hall is comprehensive. No recent New York City mayor has gone on to higher office. None of the 20th century’s most iconic leaders of Gotham – Fiorello La Guardia, Robert F. Wagner Jr., Lindsay, Ed Koch and Giuliani – went on to win another race. Wagner lost a 1956 U.S. Senate bid, despite having the Democratic and Liberal Party lines in left-leaning New York. Koch lost in the 1982 Democratic gubernatorial primary to Mario Cuomo, whom he had bested in the mayoral primary five years earlier. Giuliani aborted a rocky 2000 U.S. Senate campaign. These, it bears repeating, are the mayors who were sufficiently popular to win reelection. One-term wonders Abraham Beame and David Dinkins didn’t get sent on to Albany or Washington, D.C., either.

Nor is the phenomenon limited to New York City. A 2017 study from Boston University examined mayors of 196 of America’s largest cities – nearly 700 American mayors – elected or appointed from 1992 to 2015. Fewer than one-fifth of the mayors ran for higher office and fewer than 15% won a primary. Only 5% actually won a general election. No American mayor has ever gone directly to the White House. The only three ex-mayors who became president – Andrew Johnson, Grover Cleveland and Calvin Coolidge – later became governors before stepping into the Oval Office. And, except for Cleveland, who was mayor of Buffalo, the other two didn’t even lead large cities.

This suggests a broader truth about the mayoralty as a job category: It becomes a political liability. Running a city is a messy endeavor and doing it gets one’s hands dirty. Competing interests must be balanced, often leaving no one fully satisfied.

Stuff happens - and the bigger the city, the more stuff happens.

No one wants to run for president, or even governor, as an enemy of the teachers, police officers and firefighters unions – but no one wants to be viewed as their tool either. Keeping these public employees happy while also mollifying their counterparts, such as civil rights activists, communities of color or education reformers, may be unachievable.

Also, stuff happens – and the bigger the city, the more stuff happens. Mayors get blamed for budget deficits created by recessions, crime waves caused by national social conditions and – in the case of New York City’s tabloids and de Blasio – summertime blackouts. “Being mayor of New York City is an extremely difficult proposition,” Jackson said. “So many different ethnic and religious groups and neighborhoods – to make everybody happy is impossible.”

Bloomberg’s record of encouraging aggressive policing tactics like stop and frisk is going to impede his appeal to black and Latino voters. Just take a look at de Blasio – who was heckled during a Democratic presidential debate in July because the cop who asphyxiated Eric Garner was still employed by the New York City Police Department – and you’ll see that it might be impossible for any New York City mayor to keep his policing record clean enough for Democratic voters. De Blasio was elected as a progressive criminal justice reformer, but the mayor operates within structural constraints. In his first term, after rank-and-file NYPD officers protested de Blasio’s anti-police brutality rhetoric with a costly work slowdown, he backed off of his push for police accountability. Nonetheless, New York’s police unions were enraged that Officer Daniel Pantaleo was eventually fired, and their anger haunted de Blasio’s abortive presidential bid. “De Blasio had the police unions following him around (on the campaign trail) because of the Eric Garner thing,” said Ester Fuchs, a public affairs professor at Columbia University and a former adviser to Bloomberg. “First he had the Garner people following him, and then he had both.”

Policing is not the only key issue on which the mayor’s hands are tied: The city’s power to shape the housing market, set tax rates and integrate its schools are limited by the state and affected by the actions of suburban towns. The result is a mayor vulnerable to charges that he failed to reduce homelessness or traffic, and failed to improve affordability or mass transit. Take New York City’s epidemic of homelessness, which is a byproduct of its imbalance between booming demand for – and dwindling supply of – reasonably priced housing.

Lindsay had the misfortune of being mayor during the tumultuous late 1960s. Rising crime and strikes by transit workers and sanitation workers made him look like an incompetent manager. U.S. Sen. George McGovern of South Dakota, who bested him in the 1972 Democratic presidential primary, did not have this problem.

The contrast between McGovern and Lindsay speaks to another particular disadvantage for New York City mayors: being closely associated with a huge city during a presidential race. “You have some fundamental divisions in national politics, which historically play against New York City mayors – around race, around the rural/suburban/urban divide and around regions,” Fuchs said.

“New York mayors are viewed as part of the governing elite rather than the ‘real Americans.’ Post-1960s New York is seen as ‘not America.’” – Ester Fuchs, Columbia University public affairs professor and former Bloomberg adviser

Partly, that’s structural: The early primaries are held in small, mostly rural states, such as Iowa and New Hampshire, which puts urban candidates at a disadvantage, as does the Electoral College’s overrepresentation of less-populated states. And, of course, some of it is sociocultural. New York City’s diversity, liberal politics, high density and agglomeration of media, finance and technology can make the city the embodiment of foreign or coastal cosmopolitanism. “New York mayors are viewed as part of the governing elite rather than the ‘real Americans,’” Fuchs said. “Post-1960s, New York is seen as ‘not America.’”

Even at the state level, upstate and suburban voters can resent the city, a phenomenon that famously harmed Koch in his 1982 gubernatorial bid. In fairness, these voters didn’t just imagine Koch’s snobbery: He dismissed residing in the suburbs as “wasting your life” and mocked country living as “wasting time in a pickup truck when you have to drive 20 miles to buy a gingham dress.”

That campaign-killing quip demonstrates one possible reason New York City mayors can’t go far in politics: Typically, people who get the job have an arrogant, combative personality better suited to the hypercompetitive environment of the city that never sleeps than to connecting with farmers over corn dogs at the county fair.

To be fair, being mayor of New York City is also the only reason that anyone would have thought of de Blasio, Giuliani or Bloomberg as potential presidential material in the first place. It’s not like they would necessarily have had a better political career had they never become mayor. But when rising stars in Congress, such as Reps. Hakeem Jeffries and Alexandria Ocasio-Cortez, are rumored to be mulling a mayoral bid, it’s worth asking why they’d see that as a smart career move.

Substantively, the job is arguably better preparation for the presidency than serving in Congress or a statehouse. New York City has a larger budget than all but a handful of states. “New York City mayors are the most important in the country, not just because it’s the biggest city, but because it has a strong mayor,” Jackson said. “In a lot of cities, they have a commission form of government. And now the job includes the schools, which is a gigantic responsibility.”

But once they step into the presidential ring, they quickly get bloodied. The mayoral disadvantage may be a subset of the perverse fact that presidential aspirants seem to go farthest when they have the least political experience. Longtime senators such as John Kerry and Joe Biden have seen how having to cast votes and speak publicly on every major issue for decades can be used against them later, when the political winds have shifted. By contrast, recent presidents such as Ronald Reagan, George W. Bush and Barack Obama averaged around eight years in elected office before ascending to the White House. One can see the apotheosis of this trend in President Donald Trump, whose total lack of political experience afforded him the freedom to campaign as an outsider and to invent whatever position best suited him at the moment.

“Ironically, a record in government becomes an albatross for candidates,” Fuchs said. “And a lot more is known about New York City mayors than Arkansas governors. It’s easier to discredit them.”

Perhaps that’s why the mayor who outlasted de Blasio in the primary is Pete Buttigieg of South Bend, Indiana, the state’s fourth-largest city. Even he, though, has a police brutality and race relations problem.

All that being said, Bloomberg may yet defy history. New York City is no longer the crime-ridden, chaotic embodiment of urban decay, and the media mogul can claim his share of credit for the turnaround. As the parties have grown more polarized along racial and ideological lines, the dwindling number of rural white Democrats – who could be turned off by a big city mayor who hates guns – may no longer be an insurmountable force in the primaries. That’s especially true for a multibillionaire, who won’t rely on doing well in the early states to generate momentum, media coverage or donations. Bloomberg’s unusual strategy could be to skip some of the early states and spend heavily in places like Massachusetts and California before Super Tuesday.

Bloomberg is known as the ultimate data-driven technocrat, and he repeatedly declined to run as a third-party or independent candidate because he recognized he had no chance of winning. That means his advisers must have shown him some plausible path to the Democratic nomination this time. “It’s a long shot that actually has a path to victory,” Fuchs said. “(Bloomberg) doesn’t just run a vanity race, that’s why he didn’t run as an independent. He will be a much more interesting, viable candidate than people realize at this point.”

Maybe a former mayor with an infinite campaign budget will prove to be the exception – but, if history is any guide, he just may have the wrong résumé.