DeWitt Clinton, mayor for ten non-consecutive annual terms starting in 1803 ending 1815. Ran for POTUS in 1812 DeWitt Clinton collected political offices like he was filling out a punch card, serving in the New York State Legislature, the U.S. Senate, and as Lieutenant Governor and Mayor of NYC. However, the biggest prize eluded him when he challenged incumbent James Madison in the presidential election of 1812. Losing one of the young country’s closest-ever elections didn't sour Clinton’s commitment to politics and he went on to serve as Governor of New York.

A. Oakey Hall, mayor 1869-1872. Didn't run, but expressed interest in presidency. Also known as “Elegant Oakey,” Abraham Oakey Hall had a reputation for fancy dress and elegant manners. His debonair appearance was one reason his friends would often speculate about his destiny for higher office — specifically the Oval Office. This was not meant to be, but Hall made a career advocating for free speech, even serving as anarchist Emma Goldman’s lawyer. However, this finely-dressed gentleman met an ignominious end, suffering a mental breakdown and absconding to London for much of his later years following his service as mayor.

George Brinton McClellan, Jr., mayor 1904-1909. His father ran against Abraham Lincoln in 1864. The 93rd mayor of NYC never ran for president himself, but he was the son of an infamous presidential candidate. McClellan Sr., a Union Civil War general, ran as a Democrat and tried to oust President Abraham Lincoln. General McClellan and President Abraham Lincoln developed a contentious relationship after McClellan failed to pursue General Robert E. Lee’s Army following the Battle of Antietam. Tensions between McClellan and Lincoln led the former to launch a doomed presidential campaign. The election led to a resounding reelection victory for Lincoln — 212 electoral votes to 21.

John Lindsay, mayor 1966-1973. Ran for POTUS 1972. John Lindsay’s first term as mayor was marred by a transit strike, teachers’ strike, and a sanitation strike, as well as a devastating blizzard that brought 15 inches of snow and extensive disruption of the city. After all that, taking the job of president must have seemed easy by comparison. So Lindsay switched from the Republican Party to the Democratic Party and began a bid for the 1972 presidential nomination. The campaign was unsuccessful and quickly abandoned. Lindsay served another term as mayor before his (literal) second act. He started an acting career by taking a role in the film Rosebud, appeared at The Tony Awards, and was a frequent guest host on ABC’s Good Morning America. In his later years, he even published a novel, The Edge.

William Jay Gaynor, mayor 1910-1913. Didn't run, but expressed interest. Nominated to the mayorship by the notorious Tammany Hall political machine, Gaynor could have settled into a comfortable life of cronyism and grift. Instead, Gaynor proved himself unbiddable and incorruptible, so much so that Tammany Hall refused to support a second-term run. His aspirations to the presidency were cut short when he was shot in the throat by a would-be assassin. While he survived the gunshot wound, the bullet remained lodged in his throat until his death from a heart attack three years later.

Michael Bloomberg, mayor 2002-2013. Ran 2020. 935 million dollars. That’s how much Michael Bloomberg spent seeking to secure the Democratic Party nomination for the 2020 presidential election. Setting the record for the most expensive U.S. presidential primary campaign, this eye-popping figure represents a small portion of Bloomberg’s fortune as the 16th richest person in the world (according to Forbes in 2020). The wealthy businessman served three terms as NYC mayor as a Republican, but registered as a Democrat in 2018. He is best known for his technocratic governing style, treating the Big Apple as a business.

Rudy Giuliani, mayor 1994-2001. Ran 2008. Infamous for his “tough on crime” policies that included stop and frisk — Rudy Giuliani embarked on a “civic cleanup” of NYC during his tenure as mayor. However, he is probably best known for serving as mayor during the September 11, 2001 terrorist attacks, which propelled him into the national spotlight. Capitalizing on the wave of public support following the attacks, Giuliani began putting out feelers for a potential run, and raising major cash. Despite being initially viewed as the front-runner, Giuliani ultimately failed to convert his popularity into votes, and the campaign collapsed. Giuliani disappeared from the public spotlight, only to reemerge as part of President Donald Trump’s legal counsel, and as a key figure in Trump’s impeachment.

Bill de Blasio, mayor 2014 to present. Ran 2020. Bill de Blasio is notable not only for being the tallest mayor in NYC history at 6’5, but also for being the first incumbent NYC mayor to run for president since John Lindsay. De Blasio joined another former NYC mayor, Michael Bloomberg, in the battle to secure the Democratic nomination for the 2020 presidential race. But after receiving consistently low poll numbers, de Blasio dropped out of the race and endorsed Bernie Sanders.