If there is no hope, no dreams then humanity would come to an end pretty quickly. I know I sound dramatic but it is the truth, the shirt on that guy may be as a funny statement yet every single gambler including me have objectives when playing even when someone is fully addicted they still have objectives. This guy just want to be funny in a meaningful way and that statement looks good and also give hope to people feeling hopeless which is a good thing. I like these type of guys honestly finding fun even in the middle of big losing sessions.
Admittedly, hope is an important driving force in our life. But I think the word hope is used a bit misleadingly here. If that hope repeatedly push you into an action where your losses are high then it is no longer just hope. Have you heard of near miss in slot machine? Just play one more time and maybe I'll win, that kind of feeling can keep you playing longer than real possibility.
Many gamblers say to themselves, I'm not addicted to gambling, I'm just playing to win big. It's actually a false excuse, it's not really hope, it's addiction.