Mommy's Little Monster is such an interesting episode, since it's clear that Jim Gordon's got a massive weak spot, and that is Oswald Cobblepot. It's not just that Jim knows Oswald well, he is willing to bend over backwards to believe the best of him if given the chance. When Galavan comes to the GCPD with the lie that Oswald attacked him, Jim is quick to question every suggestion that Oswald is behind all of the crimes (that Galavan was really committing).
And Galavan clocks it, it concerns him, but he assumes it's Jim's morals that are potentially impeding him, which Jim also then explains is the issue, except Jim tactfully leaves out that he's only willing to go after Oswald if he is 100% guilty, an exception he makes for no other criminal.
And Galavan tries to manipulate and dominate Jim at the end, subtly, but he does it, and immediately Jim's suspicious (which is also interesting because Galavan imploys an abusive tactic that Barbara used to use on Jim, blaming him and wearing him him down as the one to blame, to justify her own actions. So I assume he learnt that tactic from Barbara).
But at the end of the day, people don't realise Jim Gordon is not exactly as he appears, he's not a blind follower of the law, and he's not an idiot, he understands the darkness in people just as easily as he sees the good. The issue with Galavan is that he assumes Jim hasn't been worked over by the mob already, he's resentful of being "Penguin's Bitch", he assumes the relationship is antagonistic. But Jim is, for better or worse in sickness and in health, tied to Oswald, and it's one that was built on mutual benefits and trust that is nearly unbreakable. And it's directly contrasted to Silver's manipulation of Bruce, because one is falling for the facade, choosing to distrust the judgement of an old friend who isn't squeaky clean (Selina/Oswald) over the new, supposedly kind and sympathetic "friend" (Silver/Theo Galavan).
And even when it comes to being in the front of a gun and about to be murdered by Zsasz, Jim chooses Oswald.
And it's what Galavan underestimates. He underestimates the bond. He underestimates Jim Gordon being loyal to a criminal despite all evidence to the contrary. He doesn't think that when given the choice to uphold the law or let him die, Jim Gordon will choose Oswald's word over everyone else's.
The fatal flaw of villains like Galavan and Sofia Falcone is they think Jim's easy to control, easy to read, but Jim's already sold his soul to the devil, as it were, and at the end of the day, if it comes to a choice between another evil and Oswald, Jim Gordon will choose Oswald.
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