I think I have to go with Barbara on this one. Sarah’s death was pretty shocking, but it wasn’t as evil as crippling Barbara and leaving her for dead.
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I agree because of intent. The intent to leave Barbara alive for it to haunt her, and torture Jim is some serious evil
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That’s close, but I pick Barbra Gordon’s incident mostly because of the stuff that followed. That shot debatably wasn’t even the worst of it.
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I say Sarah- he holds a gun to a baby, then tosses it. Sarah catches him or her, but Joker doesn’t know thats going to be the case. Babies are fragile, so the whiplash may have still injured the child. And Joker rewards Sarah’s heroic act with a bullet.
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Man, I should have read your post before I voted. Great point!
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Not sure that I can co-sign this take @TheTerribleToyman. While Essen’s death at the hands of the clown was imminently tragic, ultimately GCPD LT. Sarah Essen was (most heroically) doing her job and understood the risks involved, especially in a crime saturated environment like Gotham.
On the other hand, Barbara Gordon was pretty much out of the mask gig when the maniac came calling at her apartment. My gurrrl had recently completed a successful tenure in the US Congress, and after she finished some particularly personal business with a violent assassin by the name Cormorant Barb was just beginning to suss out a new way of helping the other capes in the DC universe via her incredibly gifted understanding of computers and their potential uses in the war on crime. She was ready to relinquish her full time mantle of guardian over the city to Bruce, Jason, and Dick. She was ready to spend more time with a father that she loved so dearly right down to the bottom of her heart. She was ready to be Barbara Gordon and only Barbara Gordon. This time and forever. But none of that was known by the Joker, nor would he have cared- to him Barb was simply an avenue to get to Jim Gordon in just another of his exercises in mindless terror. And all he had to do in order to see his plan come to fruition was to wait patiently until Barb answered the door…
My gurrrl got dealt the worst of it. And in many ways to this day she’s still getting dealt the worst of it. 
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Wow, @DefinitlyNOTJackRyder, this is a tough one! As evil as killing Susan was (and it was pretty evil), I have to go with shooting Barbara as the more evil act. He shot he only to make her and Jim suffer and remind them of what he could do for the rest of their days. Great question!
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It was definitely awful what Joker did to her, but as awful as it was- she is still alive. Tormented? Sure. Struggling? Yes. But left alive is still better than shot dead.
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I agree, dead is worse 
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And she seems unafraid of joker. During black mirror, Gordon voiced his concerns about joker being free and coming to get her, and she straight up says “let him.” She’s tough as nails. Sure she has nightmares, but she’s ready for him if he ever tries that again.
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Morally, definitely killing Sara, but the shock value of attempting to kill and subsequently crippling a beloved character like Babs resonated with everyone more so it was more impactful.
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I’m sorry if this comes off rough but you do realize this is Joker’s act and sure she understands the risks but what does that have to do anything with the crime committed. I’m not saying that paralyzing Barbara wasn’t awful it was, but I just think that Sara Essen’s death is awful and doesn’t need to be iconic to be one of the number 2 most evil Joker moment
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Both are horrible, but I’m going with Sara’s option, for the same reason that @TheTerrificToyman had stated previously. While Babs may still struggle with some of the trauma, understandable, having infant babies involved… that takes it for me. I’ve also become a lot more emotional when it comes to babies these last few months, so yeah…
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