Gil is an asshole.
I think the issue is that all of the characters are deeply involved with the over all deep plot, the 'Real Game' so to speak. They are all caught up in their own personal drama and pain as well as this weird assed conspiracy with freaky lizard chicks, rogue AIs, and big world powers.
Gil, on the other hand, is a nobody. He had his drama before the game started and it's over. It wasn't very conspiratorial or anything like that either.
How that plays out is that everyone wants to walk into a meat grinder to follow the whiff of an idea that might be a plot thread for their drama with no thought to their, or others safety. Gil on the other hand is more even headed, he sees the danger (real and imagined) and wants to steer clear of it.
He's also a bully, he doesn't get into fights he can't win. But he's also self destructive so the longer he is idle the more his risk aversion goes away.
He bullies his friends because he's an asshole and it's all he knows, he's a very broken person. But don't mess with his friends. He almost killed Dunk in the bar. His intention was to go to the bar and get into a fist fight but when Dunk looked like he was going to hurt Jr Gil was moments from killing him.
Going to train rather than Amboy or whatever it's called wasn't really my goal. OOC I knew that the characters wanted to go to the bunker for whatever reasons and the Gil had zero connection with any of it. I had him throw out the plan for the train as IC it was a safer play with a more known reward and OOC I knew it would make the characters start talking about the real reasons (or lie a LOT) on wanting to go to the bunker thus making for an interesting RP scene. I honestly thought we'd be heading to the bunker by the end of it but Jr started dropping Real Game bombs which caused the whole thing to break wide open.
The Chicago thing was a meta decision (I was OOC-ly helping Dan from the conversation on the ep, he never asked me to do it but I gave him the assist anyway) but something Gil would have done. All this conspiracy crap is flying way over his head and all he knows is that someone is trying to manipulate and hurt his friends, so he wants to take them away from that but his plan is nonsense. If someone had called him out on it he wouldn't have been able to defend it.
Also, Gil really is an asshole.
