Regarding Srila Prabhupada’s regulation against gambling, its very easy to understand why “direct” gambling is bad. For one, the majority is rigged against the bettor, the house always wins eventually. It is basically just thievery. Second, people often get into debt due to addiction to gambling, enter into terrible arrangements involving loan sharking, where criminal elements prey on them using a system where they are not allowed to pay off the principal of the debt and remain debtors forever.
There are many interviews you can find of people who took loans from the mob and ended up paying many times the money they owed because they won’t allow you to pay the principal in installments. You have to close the debt in full at one time, which no one is capable of. As a result you are stuck paying the weekly interest forever which builds up to many times the money you owed.
Loan sharking is perhaps more evil than gambling, and it exists in every community. In India it is often ran as pawn shops by certain castes and communities that take in people’s gold jewelery against loans, usually in low income areas. The system is rigged for them to default and lose their gold. Taking such loans is also gambling, and you eventually become a victim of the rigged system, losing far more than you borrowed.
How are any of these things good? People who gamble and become addicted get stuck in debts, which destroy families and take food away from their own children. With gambling there is always a loser, there is always a victim. Even if you gamble just among friends, one of you wins and one of you loses.
If you look into stock manipulation, which has existed for a very long time, you will find the stock market is also gambling because it too is rigged, but more subtly. Ultimately when someone is making money they are taking that money from another real person, and in these transactions there are no fundamental actual assets that they are transacting.
Should a devotee of God engage in such a corrupted activity as gambling? It’s quit obvious they shouldn’t.
What is “gambling” isn’t a solid black and white line of division, and there are various degrees, some more dangerous than others. Everything in this material world is a type of gambling, and people have to decide what risks they are willing to take without affecting their consciousness. In Srila Prabhupada’s case I believe he was even angry when someone had invested his funds in Gold, and had them liquidate it for a loss. Harikesa Swami went insane after losing huge sums of money in the Russian stock market (among other reasons). Danger at every step. Some dangers are small and some are larger.
There is the danger of getting into a purity spiral where you take things to such extremes it becomes ridiculous. For example what is intoxication? We can all agree beer and drugs are intoxication. Then some will say tea and coffee are intoxication, that’s more debatable. Other’s will spiral and say sugar or chocolate are an intoxication, maybe even cooked food. There is no limit to what someone can claim is an intoxication, but reality doesn’t always match such claims. Our aim isn’t to create an endless loop of more and more complex rules. Srila Prabhupada gave us some basic guardrails to protect us in human society from being exploited by evil addictions.

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