Hmm wait, I see them as lucky and unlucky gamblers regardless of the greed issue, it is a fact that we never know what will happen at the end of the game and in the scenario of the second person you mentioned who managed to cash out his winnings I think there is certainly a possibility for him to eventually suffer the same fate as the first person who lost all his winnings if for example at that time he was too late to cash out and preferred to continue the game.

On the other hand in the context of perspective of course everyone has different assessments of the behavior and actions taken by others and in the scenario of the two people you mentioned above I think the gambler who eventually lost his winnings again can clearly be called a greedy and problematic gambler because he preferred to continue the game instead of cashing out after successfully achieving the win.

But on the other hand, I also cannot be sure that my assumption is correct because if, for example, the gambler prefers to continue playing after winning with the aim of seeking more pleasure and not to increase the amount of winnings, then in my opinion it cannot be called greed, meaning that we must first know what the person's goal is in continuing the game after winning if we want to know whether he is greedy or not.