Gracie Mansion: Where Dreams Go To Die

It’s been said that being Mayor of New York City is the “second toughest job in America.”  Only being President is tougher.  Of course, the President doesn’t have to deal with trying to fix the subways so how tough is his job, really?

I can understand why so many New York politicians dream of being mayor.  New York City may be “ungovernable,” as John Lindsay used to put it, but it’s still the center of both America’s culture and its economy.  Being mayor means that you’re in charge of one of the most important cities in the world.  It also means becoming an instant celebrity.

The job is also a political dead end.

Since 1665, there have been over a hundred mayors of New York City.  Only two of them have gone on to higher office after serving as mayor.

DeWitt Clinton was appointed the position in 1803, after having briefly served in the U.S. Senate.  While still serving as mayor, Clinton ran for President in 1812 and came close to defeating James Madison.  Clinton would later be elected governor.

Fernando Wood was a former Congressman who was twice elected mayor, once in 1854 and again in 1860.  During the Civil War, Wood suggested that the city should secede from the United States so that it could continue to trade with the Confederacy.  Wood’s opposition to the Civil War put an end to his presidential ambitions but he was reelected to Congress after his mayoral term ended.

And that’s it.  Others have tried but none have succeeded.

In 1940, President Roosevelt reportedly considered naming Fiorello H. La Guardia to be his running mate but it’s not known how serious Roosevelt was about the idea.

In 1956, Mayor Robert F. Wagner was the Democratic nominee for the U.S. Senate but was defeated by Jacob Javits.  That same year, Wagner was briefly a candidate for the Democratic vice presidential nomination but lost to Estes Kefauver.

John V. Lindsay, who was once compared to JFK, probably could have been named Nixon’s running mate in ’68 or been appointed to Bobby Kennedy’s senate seat if he hadn’t made an enemy of Governor Nelson Rockefeller.  Instead, the Republican Lindsay ended up switching to the Democratic Party in 1971, running unsuccessfully for President in 1972, and making a final and futile grasp for political relevance by running for the U.S. Senate in 1980.  (He came in third in the primary.)

Ed Koch tried to parlay his national popularity into a run for governor in 1982 and was defeated in the primary by Mario Cuomo, whom Koch had previously defeated in the 1977 mayoral election.  Upstate voters were not as enamored with Koch as New York City was.  (And the city would later turn on Koch in 1989, rejecting him in favor of David Dinkins.)

The presidential campaigns of George B. McClellan, Jr., William Jay Gaynor, Lindsay, and Rudy Giuliani all failed to go anywhere and Mayor Bill de Blasio’s 2020 campaign has become a national joke.

And then there’s a case of Michael Bloomberg, who flirts with an improbable presidential run every four years.  Because he’s rich, Bloomberg is always taken seriously as a candidate, despite the fact that his every attempt to influence policy outside of New York has been a flop.

The most successful politician to run for Mayor of New York was someone who not only lost the election but came in a poor third, behind the winning Democrat and an insurgent socialist.  Teddy Roosevelt may have lost the 1886 mayoral election but, 15 years later, he would become President of the United States.  Would Roosevelt have ever become President if he had won that mayoral election?

Gracie Mansion is where dreams go to die.