A. Not really. Due to the high stakes and irrational risks involved, few give up their money whole-heartedly. Exceptions include when (smaller amounts of) monies go toward a charity, people are more willing to give it up as goes to a good cause anyways. Some limited recreational gambling may also be permissible as long as the context and boundaries are very clear, which they often are not. The Talmud doesn’t think much of people who gamble regularly for a living, and considers them unfit for testimony. A charity raffle and the like are exceptions where larger amounts are still kosher, because the “gambling” factor is clearly secondary. (Another issue is with the atmosphere that comes along with the territory, but that’s not about gambling itself).