Time and time again, Theo Galavan has proven that he's the most complex villain that Gotham has ever seen. And even after pushing Penguin to the breaking point by killing his mother, Gertrude Cobblepot, Galavan was elected mayor of Gotham, dodged an assassination from Penguin, and made an enemy of Detective James Gordon. Jim openly admitted that he believes Penguin's (true) story about Galavan forcing him to briefly become a mayoral assassin and firestarter.
Penguin suggested that Jim will be in his shoes soon, with someone he cares about in danger because of Galavan. Whether knowingly or not, Penguin has created one of the central mysteries of the season: which person in Gordon's life would devastate him the most to lose? And how will Galavan go about making that happen?
Bruce Wayne, who has a close relationship with Gordon, has been drawn in by Galavan, though it's unclear whether or not Jim knows about young Bruce's relationship with Silver St. Cloud, which has brought him even closer to Galavan. And the detective definitely doesn't know that Galavan's plan is to murder Bruce in order to avenge his disgraced family.
Barbara is the only person that Gordon is or was close to who's wrapped up in Galavan's schemes directly. Obviously Barbara hasn't been involved with Jim romantically for a while now, but she still feels a connection to him, either because of her own psychosis or because she's right, and it's possible that she'll marry him, like she does in the comics.
Dr. Thompkins, between her adventures in nearly catching Ed Nygma red-handed with the corpse of Kristen Kringle and her very near miss at the magic show where Barbara and Theo killed Jerome, has been constantly falling into jeopardy. And it seems like she — or at the very least, her relationship with Jim — could be in danger. Remember, Galavan knows that Jim and Lee are together, and he now knows that Jim is planning to take him down.
If Galavan targets Jim the way he did Penguin, I'm afraid that Lee could receive the same brutal treatment as poor Gertrude. Hopefully Jim can stop Theo before he uses any more innocent loved ones as part of his evil scheme.
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