Was there ever a mayor worse than de Blasio?

In September, Rep. Max Rose put out a digital ad that just consisted of him yelling, “Bill de Blasio is the worst mayor in the history of New York City!” It didn’t deliver Rose a second term, but it did earn a retort from the mayor’s press secretary Bill Neidhardt, who countered that Fernando Wood, who served during the Civil War, was worse. Looking back 150+ years to find a mayor worse than your boss is certainly a take, but as the city looks down the barrel of another pandemic shutdown, and everyone’s eyes are turning to the 2021 candidates, it’s worth taking a look back at other contenders for the worst mayor we’ve ever had.

Fernando Wood (1855-1858 and 1860-1862)

Mayor Fernando Wood proposed seceding from the nation to maintain business with the South. Terrible idea, terrible mayor – even by 19th-century standards. 

Jimmy Walker (1926-1932)

Mayor Jimmy Walker (aka Beau James), who served during the Great Depression and resigned in a corruption scandal, was notorious for never getting to work before 3 p.m. Does that make Mayor Big Bird an early bird, too?

William O’Dwyer (1946-1950)

Mayor Billy O’Dwyer was caught up in a corruption scandal so huge that when he resigned, President Truman threw him a lifeboat in the form of an ambassadorship that allowed him to flee to Mexico.

Rudy Giuliani (1994-2001)

Has any modern-day Hizzoner fallenfurther from grace than the guy trying to dismantle our democracy? Some argue that Giuliani was a good mayor in his day – it’s a common refrain that he “cleaned up the city” – but beyond his well-established history of erratic behavior, the many, many New Yorkers who were unjustly detained by his stop-and-frisk policies would beg to differ.

Michael Bloomberg (2002-2013)

Sure, a lot of people call him the best of all time, crediting him with building a safe and prosperous city after 9/11, but his many detractors accuse him of crushing small business owners’ prospects, exacerbating homlessness despite his best efforts to pay homeless individuals to go anywhere but here, and dialing stop-and-frisk up to 11.