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#anyway the red robin one doesn't quite fit this list because it's way lower-stakes - no one's in physical danger
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Dick + 5 Sophie's choices ("What's it gonna be, kid?")
I tried not to copy-paste entire comics here but this is still kind of image-heavy??? Anyway Dick has a lot of trauma surrounding Sophie’s choices and it’s a recurring motif going back to the Dick and Tim Batman-and-Robin run and I’m a LITTLE BIT OBSESSED.
1. Robin: Year One 2 - Bruce vs. Judge Watkins/Meany
Two-Face is threatening both Bruce and a civilian
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Two-Face: The Batman and Judge "Let 'Em Go" Watkins. Their fates are sealed. Double death penalties. Of course, there are a few side bets open. Bruce: No... Don't play his game, Robin... Two-Face (hitting him): You've had your last words!
1a. Robin 0 - Bruce vs. Judge Watkins/Meany
Dick tells the Two-Face story to Tim; here the judge's name is Meany instead of Watkins, but it's the same story
(fun history note: this is the comic that introduced Dick's history with Two-Face - Robin Year One came out later and expanded on the story told here)
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Dick: I almost failed him. I couldn't save Meany and I nearly got Batman killed. Tim: It was a no-win situation, Nightwing. You both came out alive. That's what's important. Dick: I know you're right. But it doesn't help.
2. Detective Comics 680 - Prodigal 7 - Tim vs. civilian
Dick has to choose between saving Tim from Two-Face and saving a civilian
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Two-Face: “Well, the first Robin I ran into didn’t do so well. I put him in traction. Did my best to kill him. I could smell the fear on him. I got to him. I own him. Just like I’m gonna own Batman when he finds out I killed his new Robin. What do you think his reaction’s gonna be, kid? (Dick, as Batman, is hiding in the rafters watching. He has a flashback to childhood with Two-Face asking the same question: What’s it gonna be, kid?) Two-Face: “Here’s the game... I cut one of these lines and one of you gets crushed under a ton of paperwork.Two thousand pounds, to be exact.” (Dick shuts off the lights and attacks Two-Face directly.) Narration: No psychology. No reverse logic. He can't win by playing Dent's game. He has to make it his game. His rules.
3. Gotham Knights 11 - Tim vs. Bruce
Dick has to choose between saving Tim and saving amnesiac!Bruce
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Hugo Strange (to Dick): “It’s going to take a choice. You can take Mr. Wayne home, or you can save your little associate over here. Now, of course we all know that the Boy Wonder can take pretty good care of himself. But that's even more true of Batman over there, so as I understand it, Nightwing, your instructions are to help Robin first. [...] Dora and I will shoot on the count of three. Ready, Dora? One - two -” [...] Dick: “Robin -?” Tim: “Him.” [Tim throws off Hugo Strange while Dick saves Bruce.] Dick: "Good job, Robin." Tim: "I think we lost Hugo." Dick: "Yeah, but we didn't lose you. No thanks to me." Tim: "Oh, hey, you don't -" Dick: "Shh, take the compliment. You did everything right."
4. Nightwing 138 - Tim and Damian vs. assassins
Dick has to choose between saving Tim and Damian and saving some poisoned assassins
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Dick (internally): I have less than thirty seconds to save them. Can Damian and Tim hold out that long…? Damian (captured): So…I do embarrass myself. Tim (to Damian): Don't move - I'm almost there! Damian: And I am forced to at least thank you for trying… Dick (internally): Twenty seconds. What’s it gonna be, Dick? Save them…and sacrifice Tim and Damian? Tim: Nightwing! Dick (internally): I'm sorry, Tim...  (He runs to save the assassins.) Alfred (over the comms): Master Dick - they are leaving! Dick: Activate Tim’s tracer. Give me fifteen minutes. Alfred: Were you hurt? Dick: No. I was played.  (internally) I’m coming, Tim... I’m going to save you..
5. Red Robin 1 - Tim vs. Damian
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Tim: I don't call this "okay," Dick. Dick: He's my responsibility, now. You're not my protégé, Tim... You're my equal. My closest ally. You'll be okay. But him... Tim, you know better than anyone that left on his own, he's going to kill someone. Again. You have to understand - Tim: No. I don't. This is all I have now. [...] How can you let him wear that costume, Dick? What earth are we on that you choose him over me?
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