You said he looked like an idiot and justified it using Pacifista and Rayleigh as reasons. He didn't go there expecting to encounter Rayleigh and the next Pacifista, so you can't really blame him for being "unprepared" unless you're expecting him to see the future. Because they're the reason why things went down the way they did, not because of Hancock—the person he's actually supposed to be prepared for. From the looks of it, he's prepared enough for Hancock given how he dealt with her.
I said he failed to get what he wanted over being afraid to challenge Ray (as Rayleigh implied). The Pacifista and Rayleigh panic just made him look weak.
As for Boa, he was not prepared, otherwise he wouldn’t be in a situation where he wasn’t sure whether to kill her or not cause she’ll turn them to stone lol.
Just to then run away cause Ray appeared 🤣
Hisss actions are a mess.