Past, Present, and Future
One of the baffling things about our existence is the one-dimensionality of time.
For all we see ourselves as having free will, souls, and consciousness, the past extends behind us in a single line. There are no multiple pasts. There is only one. I'm not talking about conflicting narratives of the past, or course. I am assuming that only one thing actually happened, even if we all view the event differently.
The same applies to our future. There may be multiple possible futures, but in actuality there is only one future. The possibility space extends like a cone into which our present travels as a bead on a wire. Someone with infinite knowledge of the present should be able to follow the path through to the future, assuming that infinite knowledge includes what leads people to choose their own actions. Our choices affect the path, but in the end, only one reality will exist, another point on the fading line of our history.
All of this assumes that one could, somehow, outside of time, view the present moment traveling along this path. Free will makes the choice. But there is knowledge that only one choice can eventually be made. That is our future.
Judaism sees the giver of charity as more blessed than the recipient. The logic is a little tortuous, I must say.
The recipient is already destined to receive or not receive the gift. What isn't destined is how the recipient will or won't get it. Each person is already destined to have or not have their money. What isn't destined is how they will be gaining or losing it.
A giver of charity is utilizing a precious moment to give away money that he was going to lose anyway to someone who was going to get it anyway. In essence, he simply makes the choice to be the vessel for the transaction. That makes the gift a blessing for the giver. The recipient was going to get the money anyway, and the giver was going to lose the money anyway. But the giver acquired an opportunity to gain a blessing in the process.
In this way, charity's ideals play with the strange concepts of both free-will and destination at the same time.
Levels of Charity
The Rambam speaks of eight levels of charity:
The highest level is to invest in a person so that they they are able to overcome poverty.
This level may require no giving at all on the part of the giver; all that may be required is a loan. In fact, it may even result in the giver gaining a profit as a result. (Note that it has to really be an investment, and not simply a loan with interest, which is forbidden.) The net result is an end to the need for charity and no one had to be embarrassed as a result.
The next level is where neither the giver nor recipient know each other.
The next level is where the giver knows the recipient, but the recipient does not know the giver. In this way, the recipient will not be embarrassed if he ever meets the giver.
The next level is where the recipient knows the giver, but the giver does not know the recipient. In this way, the giver will not be tempted to feel haughty if he ever meets the recipient.
For the remaining levels, all parties know each other.
The next level is when the giver gives before being asked.
The next level is when the giver gives as much as needed when he is asked.
The next level is when the giver gives less than is needed, but does so cheerfully.
The last level is giving less than is needed and resentfully. Which is still better than not giving at all.
I don't know how often one has the opportunity to do the highest level of charity, but I suspect that it is more often than it would appear.
P.S. I could probably relate all this to trading and negotiation in games, but I won't.