Like you, I have seen these posts for years. But never once have I thought it had anything to do with gambling.
The way I take it - and the way I think it is intended - is more aligned with a common synonym for fearless: adventurous or bold or daring. Kind of like how it is used in the phrase 'fearless leader', which clearly has nothing to do with gambling.
I rarely reply because I seldom have a handle on how the game might go. But I always read what others have to say and I respect everyone who is willing to stick there neck out a bit and make their predictions on this very public forum.
AlbaNY_Ram