Little Sterling Archer was dressed as Hitler for Halloween. No, he has no idea why either.
Gambling may not have been one of Archer's vices prior to this episode, but Sterling makes sure he changes that.

Archer Season 2 Episode 11 Quotes

Lana: You turned archer loose with four million dollars in a casino?
Archer: Oh, don't worry. He may be vain, selfish liar and quite possibly alcoholic man whore, but gambling is one vice Sterling doesn't have.
Malory: Guess he's too busy doing all those other awesome stuff. Thanks, mother.

Malory: I am not sharing a room with you.
Gillette: No, I'm sharing it with you and it's the last room in the hotel. Mo view but it's got two queens.
Malory: Where's the other one, greasing up in the bathroom?