I'd ask the Gambling one (I ain't played KH2 in ages!I've been on FFVI) if he's lost gambling against Setzer. Before you all go "Setzer is weak and not gambler lolz",he is actually an FFVI originated gambler,owns the airship 'Falcon',is a well-known gambler and has explosive playing cards.
In KH2 he was watered down to a presumably younger and less skilled Setzer.Evidence?Look!
http://www.ffonline.com/ff6/setzer.htm
http://www.khextreme.co.uk/kh2/kh2_characters_tt.php (Scroll down)