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Summary
Dave really underestimated Trevor's influence over Michael. In my headcanon, the whole reason Dave kept Trevor around was because he hoped- or thought -that Michael would keep Trevor under control. Following my other comics, Dave is aware of the complicated relationship between Michael and Trevor, but he probably didn’t fully grasp how bad it was, seeing as he’s only heard one side of it.
He’s frustrated here because he can see that Michael is potentially reverting back to his old, uncontrollable self. And if Michael goes down by getting arrested, Dave goes down with him. His leash is starting to slip.