Worst mayor ever? Are you serious?

In a campaign advertisement, Rep. Max Rose tersely declared Bill de Blasio the worst mayor in New York City history. Rose joins a diverse coalition of people who have deemed de Blasio the worst — a list that includes de Blasio’s predecessor Rudolph Giuliani and Donald Trump.

Even if many New Yorkers would resist the impulse to tag the 109th mayor with that label, at this moment he appears to have few fans. In March, his approval rating was a tepid 40%, and approval of his handling of the COVID-19 epidemic plunged from 63% in May to 50% in July.

However, is de Blasio, who even after the ravages of COVID-19 runs a popular, vibrant city with crime still low by historical standards, truly the worst in New York City history?

Is he as bad a mayor as William O’Dwyer? O’Dwyer abruptly resigned in 1950, the first year of his second term, ostensibly to become ambassador to Mexico. However, this conveniently happened just as the Brooklyn district attorney was engaged in an investigation of mob influence in city government. O’Dwyer’s political ally, James Moran, was becoming a focus of the investigation.

Speculation persists that the mayor was escaping before the investigation exposed personal wrongdoing. Though O’Dwyer was never charged with any crime, his campaign manager testified the mayor received a $10,000 bribe from the mob. When the testimony became public, O’Dwyer resigned from his ambassadorship but stayed in Mexico City for about another decade.

Or is de Blasio really worse than Mayor Jimmy Walker? A product of Tammany Hall, Walker allowed various political wheeling-dealing to go on. He was a fan of partying at clubs and theaters, including with his showgirl mistress, and would even skip meetings with Gov. Franklin Roosevelt to paint the town. Various corruption scandals emerged, culminating in Walker himself testifying on gifts including European vacations and a stock account that paid him over $240,000. Facing the imminent threat of Roosevelt removing him from office, Walker resigned and moved to Europe, where he married his mistress.

Surely Fernando Wood gives de Blasio a run for his money in the competition for worst mayor. Under Wood, the city’s Municipal Police Force was so corrupt that in 1857 the state Legislature replaced it with a new Metropolitan Police Force. The mayor refused to disband the Municipals, and his arrest was ordered.

Wood occupied City Hall with 300 Municipals, and 50 Metropolitans arrived to arrest him, at which point the dueling forces brawled in the street. For a few months that year, the city had rival police forces, where members of one force would routinely release people arrested by the other, until Wood capitulated to a court order and disbanded the Municipals.

Wood’s woes were not over. Gangs decided that the dysfunctional police situation made for a good time to violently settle grievances with their rivals, as well as loot. The two police forces made little headway in stopping the violence and the state militia was deployed to restore order. Wood faced blame for the violence: the two police forces sued him and won a judgment of $250 (about $7,500 in today’s dollars), which he never paid.

As if Wood could not top these scandals, he was also a Confederate sympathizer. “With our aggrieved brethren of the Slave States, we have friendly relations and a common sympathy,” he said. When South Carolina became the first state to secede, Wood proposed to the city’s Common Council that New York City do the same, then become a sovereign nation. Wood went on to become a member of Congress, where he strongly opposed a constitutional amendment to abolish slavery.

Is de Blasio as bad a mayor as David Mathews? The last Colonial mayor, Mathews remained loyal to England, and New York’s provisional government found him guilty of plotting to kidnap and assassinate George Washington. Mathews managed to escape house arrest and became mayor yet again when the British took control of the city. Mathews then allegedly used the office to personally enrich himself, including deploying troops to plunder for him.

Just as de Blasio has many detractors in his own party, some of Mathews’ fellow Loyalists had little respect for him, with one describing the mayor as “profligate, abandoned, and dissipated, indigent, extravagant, and voluptuous.” When the British army evacuated Manhattan, Mathews fled to Nova Scotia, where he remained for the rest of his life.

Is Bill de Blasio, then, really worse than these four mayors? At the very least, he never opposed abolishing slavery or tried to assassinate a Founding Father. But even with those points in his favor, most New Yorkers will probably not have newfound respect for Hizzoner.