How to understand free will in Judaism? Does free will in Judaism have limits? What are these limits?
God willed for man to have free will, so that we can be “Godly”, which was the greatest gift that He can altruistically give. That being said, if man chooses something which is clearly counterproductive or if it contradicts the Godly plan, He is obviously “smart” enough to know how to maneuver in a way that man’s choice doesn’t mess things up (for ourselves!). Like a chess master who, despite his opponent’s free will, knows exactly how to react and counter-react to fit his needs (just that regarding our topic, we and God are “on the same side”). Or like a caring parent who wants to teach his child independence, yet lovingly watches over and sometimes intervenes. It’s also true that part of maturity is to choose to accept the truth from others (e.g. G-d, rabbis, and parents…) who are more intelligent and experienced (something difficult for adolescents and egoists!). In other words, our "will" isn't totally free, for we didn't choose our height, genetics or into which generation or family to be born, rather this is our Godly fate and job which is for us to destine and grow through our choices, which should be beneficially guided with the help of others. With Love of Israel, Rabbi Ari Shvat