Gavin might have slipped up a bit by missing the Kingdom’s resident tiger, but from the look of things he might be one of Negan’s better lieutenants.
Gavin has always struck me as the guy on The Walking Dead who is there to do a job and nothing more. He clearly doesn’t approve but he knows he has a job to do and he does it. After “The Big Scary U” we see how Gavin ranks among the other lieutenants and given his reactions he might be the most supportive of Negan’s “people are resources” philosophy out of everyone.
Gavin’s abject horror was evident when Jared killed Benjamin at one of the supply drops. It was clear in that moment that he knew that Benjamin’s death was the shot across the bow. Not only would that event galvanize the Kingdom, it would make future dealings with them very challenging and this will not be easy to explain to Negan.
(We’re already thinking Gavin might have left quite a few things out…like the Kingdom’s resident tiger. Surely Negan will be discussing Gavin’s oversights after All Out War plays out)
More telling, though, is Gavin’s reaction to Simon and Regina’s plans to use the workers as bait. He’s also not happy when Rick arrives at the beginning of the episode. He uttered no fewer than two “Jesus Christs” in episode 805 because he knew he was in the middle of a madhouse. It’s one thing to follow orders in the field, but being trapped with a bunch of power-hungry madmen and terrified workers is a whole other issue.
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Gavin is smart enough to know things aren’t going well, and they go from bad to worse when Negan disappears. For that reason alone, Gavin is probably Negan’s biggest ally at this point because he gets it.