Do you think Hannibal sent Gideon after Alana because he was jealous of Will kissing her?
I think Hannibal, as always, was following several goals at once. The first and the major one was giving Will an opportunity to kill someone. This is Hannibal’s perpetual strategy: he creates a situation and gives a person a choice, watching how they are going to act.
In this case, he set both Gideon and Alana up to make a gift for Will. First he sent Gideon to Alana; then he told Will he’s worried about Alana getting hurt, left the car keys and the gun on the obvious places and excused himself. Will could choose to grab them and go after Gideon or stay here and wait for Jack to help. He chose the former and he pulled the trigger just like Hannibal believed he would. The only reason why Gideon lived was because Will felt too sick to aim properly.
This was Hannibal’s aim, but he also deliberately targeted Alana. I think all explanations apply here. He respected her and liked her, but I believe he also resented her somewhat for getting parts of Will’s attention. Not that Hannibal was truly jealous of her - he knew she and Will would never be compatible, but he’s possessive and he didn’t want Will to even entertain the ideas of building a life that didn’t involve him. So he didn’t mind getting rid of Alana. She was a misdirection in Will’s love life.
In addition, the opportunity was just too convenient to pass it up. In Hannibal’s eyes, everyone is disposable, including people he has genuine affection for - everyone but Will. He’s ready to kill whomever and sacrifice whatever for him, so he puts Will’s Becoming above the rest of the world.
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