Friend w/ Gambling Problem

It wouldn't hurt for your friend to try. In order to do the right thing, your friend must be willing to sacrifice his image. Since the reward is incredibly greater than the risk, it is a worthwhile venture. The gambler will not likely listen to this person alone, so it might be better to do some sort of intervention.

Most importantly, do not surround him with stories of playing winning poker. A friend of mine plays a lot of poker and constantly spends time with winning players. The ease of winning has become so engrained in his head that I doubt he'll ever get it out.

[AlanBostick]

It sounds like what is called for here is what addiction and recovery specialists call an intervention.