Ben's just being an idiot and trying to be funny, nothing more. You thinking he's secretly pro-Trump is ridiculous.
like... listen dude, I can agree that it's not a good joke to make, it's needlessly uncomfortable and reeks of just saying anything without thinking through how it comes across
but if you seriously think that Ben secretly supports Trump or something, which would stand against like... literally anything he's ever indicated about his politics or beliefs, that's reaching so far that it's effectively made in bad faith
I think most of you are missing the second half of the conditional statements I'm making, so I'll try to lay it out more clearly.
There are, to me, two reasons a person in media would make a Trump reference in 2019. The first is to make a shitty edgy joke. The second is to dog-whistle to Trump supporters.
Ben made a shitty "lock her up" joke. He frequently makes shitty, edgy jokes, and it's as tiresome as you're probably finding me right now since I'm not properly revering Giant Bomb. For once, for this particularly shitty joke, I would have liked to see him own that he made a shitty, edgy joke about a sensitive thing (to put it mildly) and try to do better next time. But, as usual, we get silence from Ben about it because why would he acknowledge it when no one else seems terribly bothered by it?
In the absence of knowledge, there can only be speculation. Do I think that Ben Pack is actually a Trump voter? I don't think he is; after all, he signals by retweeting Alexandria Ocasio-Cortez, right. However, I personally don't save my good faith for people who think that making Trump references in 2019 is cool, edgy, or funny, and I'll side-eye anyone who does.
EDIT:
this is to say there's a third option you're missing, which is "playing off a phrase that's been burnt into your brain without thinking about why it's there"; in this case that is just, let's say, possibly irresponsible rather than intentionally being edgy
Then he's being thoughtless about the things that he says, which again, I would have liked to see him own and try to do better next time. Instead, we get another shitty, edgy joke, this time about John J. Kirby's death.