“Ladies. Gentlemen. You have eaten well. You’ve eaten Gotham’s wealth. Its spirit. Your feast is nearly over. From this moment on—none of you are safe.

It’s with this declaration of war that the Batman first made himself known to Gotham’s elite, as told in Batman: Year One. When Bruce Wayne first put on the cowl, it wasn’t to beat back wave after wave of costumed enemies, but to fight back against the long entrenched corruption of his city that was crawling up the spires of Gotham to its peaks of power. It wouldn’t do just to take on the muggers in the alleys when the politicians who ran Gotham itself were often all the more possessed by greed and cruelty. After all, as we’ve seen recently in The Batman, if the Dark Knight doesn’t bring them down, someone far more dangerous and destructive might take the task on himself.

While corruption runs deep in Gotham, perhaps no office has a greater history of villainy, cowardice and general mismanagement than that of the mayor. It’s too soon to see how the city’s newest mayor, Jayme Lawson’s idealistic Bella Reál, will shape up. But we consulted with Gotham’s most dedicated political historians to determine the worst of all of the mayors who have come before. Here, we present the most terrible mayors to ever preside over Batman’s not-so-fair city.

The Milquetoasts

Mayor Linseed
Batman, Season 1 (1966)

There’s not much we know about Mayor Linseed as a leader or policymaker, but he does stand in as the most visible example of the earliest politicians depicted in Batman stories: virtually helpless and ineffectual against the rising tide of super-crime, were it not for the aid of the Batman. Against the likes of Catwoman, Penguin and the Riddler, mayors like Linseed have one move and one move only, and that’s to call in a guy who dresses in tights and his kid sidekick to solve the problem for him. The outward embarrassment of this systemic failure is one that future mayors of Gotham would all very specifically run against, as Gotham administrators like the DC Universe’s current Gotham mayor, Christopher Nakano, seek to wrest control of their city away from costumed crimefighters. But hey, as embarrassing as it may be to put your city’s safety in the hands of an anonymous vigilante, you can’t argue with the results.

Daniel Dickerson
Detective Comics #743 – Gotham Central #12 (2000-2003)

Dandy Dan Dickerson was Gotham’s first mayor after the disaster of No Man’s Land, and he was none too well liked. Although not outwardly corrupt in the way many of his mayoral predecessors and successors were, Mayor Dickerson demonstrated a disdain for the people he was elected to govern, seeking only to gain the favor of Gotham’s wealthy elite. Like many of Gotham’s mayors, Dickerson died in office, in his case to a sniper’s bullet. Who knew the Joker was such a crack shot?

The Corrupt

Aubrey James
Gotham, Season 1 (2014)

On TV’s Gotham, Mayor James was a clear representation of the very politicians Batman spoke against in Year One—those organized crime puppets and white collar criminals who defined the city’s ruling class. Aubrey James was the active mayor the year that Thomas and Martha Wayne were murdered and ensconced deeply in the pocket of crime boss Carmine Falcone. No great criminal mastermind, James’ greatest motivation tended towards fear over ambition. James was eventually replaced in office after a mysterious disappearance—by his own kidnapper, no less. But he must have done something right, as ten years later, in the series finale, we find that James has been elected to office once more. Perhaps with Batman keeping crime in check, Mayor James’ new tenure will hew closer to the Linseeds of years past.

Hamilton Hill
Detective Comics #503Batman #381 (1985)

As Batman stories returned to focus on urban corruption as much as costumed villainy in the 1980s, Hamilton Hill arose as the original prototype for Gotham’s compromised leadership. Hill, too, was in the pocket of a powerful crime boss: Rupert Thorne, himself a city councilman. Time and again, Hill used his power as mayor to rid the city of Thorne’s enemies, replacing Commissioner Gordon for a time with the more pliable Peter Pauling, and framing Batman for the crimes of super-villains. In the comics, Batman exposed Hill’s corruption, and he was forced to resign. But on television, Hill is remembered more fondly in Batman: The Animated Series as the preoccupied but caring father who more or less does what’s best for the city when he’s able. In the future, Neo Gotham even commemorates his legacy by naming a school in his honor—Hamilton Hill High, attended by future Batman Terry McGinnis.

Sebastian Hady
Batman #693Detective Comics #951 (2009-2017)

Gotham historians find that most corrupt mayors in Gotham’s history are being manipulated or bullied by an outside party or interest. That wasn’t the case with Mayor Hady, who took office during Batman’s presumed death after Final Crisis. An inveterate manipulator and blackmailer, Hady had no scruples when it came to dealing with the likes of Penguin or Leviathan to serve his own best interests—even hiring Firefly to torch Gotham’s poorer neighborhoods so that his own real estate company could pick up the land for cheap. Hady was such a disastrous mayor that even the clandestine Court of Owls sentenced him to die. But while Nightwing saved his life that night, Hady would eventually meet his end to the League of Shadows.

The Actual Super-Villains

Theo Galavan
Gotham, Season 2 (2015)

This is the ambitious businessman we alluded to earlier who kidnapped Aubrey James in order to become the new mayor, because apparently that’s how politics work. Even among Gotham’s most unhinged characters and storylines, Galavan was always a standout. Galavan was a descendant of Gotham’s once influential Dumas family—as in, the extremist cult featured in 1990s Batman comics, the Order of St. Dumas—and returned to Gotham in order to seek revenge on the Wayne family which drove them out long ago in disgrace. After a combination of charismatic speeches and old-fashioned bullying won him the office, Galavan used his power to capture young Bruce Wayne and offer him up to his Order as a ritual blood sacrifice—only to be shot by Jim Gordon and mutilated by Oswald Cobblepot. But that wasn’t enough to kill him, as Hugo Strange reanimated his body to become the avenging dark angel Azrael. So Cobblepot tried again, this time swapping his umbrella for a rocket launcher. That one did the trick.

Oswald Chesterfield Cobblepot
The Batman Adventures #1-13 (2003-2004), Batman: Earth One (2012), Forever Evil: Arkham War (2013-2014), Gotham, Season 3 (2016)

No villain in Gotham has been as fiercely determined to run this town as Oswald Chesterfield Cobblepot, disaffectionately known as the Penguin. He first tried—and, through a populist campaign, nearly succeeded—to unseat Mayor Linseed in the ‘60s Batman TV series. His mayoral aspirations were rekindled in 1992’s Batman Returns. In the 2003 Batman Adventures tie-in comics to Batman: The Animated Series, Penguin got his wish for the first time and made Batman into Public Enemy Number One. Wildly unpopular with the people, who regularly organized protests outside of his mayoral residence, Penguin was unbothered, using his power to divert city funds to whatever causes suited his own fancy. Good news for the city’s birds, bad news for its citizens. When Batman discovered that Clock King had rigged the election in the Penguin’s favor, Cobblepot resigned from office before he could face consequences.

But across the multiverse, Oswald would find his way back into the catbird seat time and again. In the Batman: Earth One graphic novel, in Gotham, following the fall of Galavan (further entertaining the idea that somehow by physically overpowering the mayor of Gotham, you become the mayor), and even, momentarily, in main comic book continuity, while the world is overrun by villains in Forever Evil. Of course, Batman arrives to take the city back from him after he deals with the Crime Syndicate. But with Colin Farrell’s Penguin now empowered after the events of The Batman and with a new HBO Max series on the way, you never know what could be in his future…

Quincy Sharp
Batman: Arkham City (2011)

In the Arkham video game series, Warden Quincy Sharp rode a “tough on super-villains” ticket all the way from Arkham Asylum to the mayor’s office. What the public didn’t know was that Sharp himself was deluded into believing he was the reincarnated spirit of asylum founder Amadeus Arkham, and that Arkham doctor Hugo Strange was controlling him in order to enact his most dramatic psychological experiment yet: the transformation of much of Gotham into a lawless “Arkham City” where the criminally insane ran rampant. Ultimately ceding control of the city to Strange, Sharp was immediately removed from office after Batman took down Arkham City’s walls, just in time for the next crisis.

Harvey Dent
Batman: The Telltale Series (2016)

This list would be inherently flawed if we didn’t sneak Mayor Harvey Dent in at Number Two. Though usually a crusader for Gotham in his origins as a District Attorney, Harvey Dent realizes a mayoral ambition with (or without, depending on your choices) the help of his closest friend Bruce Wayne in Batman: The Telltale Series. But as a series of cascading tragedies shake Harvey’s worldview, the once-promising mayor turns on his city to lord over it as a tyrant. For his apparently sudden change of heart, Mayor Dent is dubbed “Two-Face” by the media.

The Worst of the Worst

Armand Krol
Detective Comics #647-699 (1992-1996)

Armand Krol doesn’t really have much of an evil streak. He was never on the take, never kowtowed to any crime lords if he could help it, and always had the city’s best interests at heart. Nevertheless, it was Krol’s poor decisions and leadership which led Gotham City down into the lowest point in its history. Like many of Gotham’s more effective mayors, Krol was elected on a platform of taking the city back from costumed vigilantes (a campaign which would, ironically, inspire Stephanie Brown, the Spoiler, to take action against her father the Cluemaster as a new crimefighter herself). This campaign left the city ill-equipped to handle the night of Bane’s “Knightfall,” when the city was overrun by escaped Arkham inmates and Krol himself was tortured into obeying the whims of Joker and Scarecrow. Left traumatized, but grateful for Batman’s help, Krol decided to reverse his policies and throw his full support behind the Caped Crusader.

Which, you know, would be great, except that following Knightfall, there was an entirely different Batman in town: the brutally lethal Jean-Paul Valley. Following the new Batman’s lead, Krol demanded that the GCPD follow suit as well by adopting more lethal tactics of their own. Commissioner Gordon refused this order, prompting Krol to replace him with a new commissioner, the woefully under-qualified Andy Howe. When the true Batman finally returned and tried to warn Howe of the forthcoming contagion which would soon sweep Gotham City unless prevented, Howe’s lack of an established relationship with Batman led him to disregard the warning. Soon enough, the city succumbed to a plague which would claim Krol himself and become one of the major factors contributing to Gotham’s abandonment by the United States for a full year as No Man’s Land. And so, with his dying breath, Armand Krol cemented his legacy as the Worst Mayor of Gotham City, Ever.

After such a catastrophic tenure as Krol’s, it’s hard to imagine even a super-villain who could knock him off the top of the list. Could there possibly ever be a more disastrous candidate for Gotham’s most public office? Well, maybe if Bruce Wayne ever decided to run. There’s something about that guy we just don’t trust.

The Batman, directed by Matt Reeves and starring Robert Pattinson and Zoë Kravitz, is now in theaters. Visit our official movie page for all the latest trailers, articles and news on the film!

Alex Jaffe is the author of our monthly "Ask the Question" column and writes about TV, movies, comics and superhero history for DCComics.com. Follow him on Twitter at @AlexJaffe and find him in the DC Community as HubCityQuestion.