7 Worst Things The Penguin Has Ever Done

3. He Tried To Kill Gordon's Wife

Batman fans need no introduction to Knightfall, the storyline that saw Bane break Bruce Wayne's back and instated St Dumas cultist Jean Paul Valley in the cape and cowl. One arc they may have missed, however, involved the Penguin making a particularly troublesome attempt at revenge against Gotham's finest, targeting none other than Sarah Essen - Commissioner Gordon's wife - in a horrific kidnapping.

The twist here is that Cobblepot actually turns himself in while Essen is missing, with the sole intent of mocking Gordon's inability to find her. Growing increasingly frustrated and desperate, Gotham's white knight resorts to the very methods he'd attempted to stamp out when he first joined the force, savagely beating Oswald in a vein attempt to extract the whereabouts of his wife, who Penguin claimed would die if he failed to find her.

The issue ends with Gordon taking the mobster to the GCPD roof, where he then threatens to throw him off the building altogether. Valley himself then appears, having rescued Essen while the pair were arguing and while ignoring the Bat-Signal too.

It's the way Penguin revels in Gordon's grief that's the most disturbing thing. It enshrined his status as a truly evil character, and though Valley's Batman came through in the end, if he hadn't, this would've been one of the cruellest comic arcs of all.