I'm not sure, it would probably depend on his assessment of the costs, benefits, and risks involved. In any event, I don't see the point of your question. You asserted that gambling opportunities did not exist in the ancestral environment; that's not so.

That's just decision making under uncertainty. I was talking about proper gambling, such as buying lottery tickets. My point is that you need some high-level ("System 2") processing to associate the action of buying a ticket to the scenario of winning vast riches, since these are not the sort of things that existed in the ancestral environment.
But if you understand probability, then your System 2 should not make that association.

Given army1987's comment I suppose it is possible to get that association from social conditioning before you understand probability.

I think you are pretty unusual; my impression is that most people daydream as far as I know.

On further reflection I think I overstated my claim. I do speculate/daydream about fictional scenarios, and I find it rewarding (I used to that more often as a child, but I still do it).

Therefore I suppose it is possible to counterfactually pretend to having won the lottery using suspension of disbelief in the same way as when enjoing or creatiing a work of fiction. But in this case, you don't actually need to buy a ticket, you can just pretend to have bought one!

But let me ask you this: Do you agree that there a decent number of people like me who are not gambling addicts but still occasionally buy lottery tickets?

Yes.

If you agree, then what do you think is the motivation?

Habit created by social conditioning looks like a plausible answer.