Here's a problem for versions of freewill theism that affirm God's omniscience (i.e. foreknowledge, counterfactual knowledge):
At this point we may picture God as an unlucky gambler. He confronted a range of options. Some were mediocre: no free creatures, or at least no significant freedom. Others offered Him a gamble on how His creatures would use their freedom. If He gambled, He might lose. Or He might win: His free creatures might freely shun all evil, and that would be very good indeed. Wisely weighing the prospects of winning and losing, He chose to gamble. He lost. Lost rather badly, to judge by the newspapers; but we don’t really know quite how much worse it could have been. Tough luck, God!
(Our commiseration for God’s bad luck seems scarcely consonant with worship of Him as a Supreme Being. However, the mysteries of the Trinity may go some way to reconcile dissonant stances toward one and the same God.)
Be that as it may, the picture of God as an unlucky gambler is wrong. Or anyway it is heterodox, which is the same for present purposes. For it overlooks God’s foreknowledge. An ordinary gambler makes a decision under uncertainty; he doesn’t know how any of the gambles on offer would turnout. When he finds out he has lost, it’s too late to change his mind. He can only regret having gambled as he did. God, however, does know the outcome of at least one of His options: namely, the one that He will in fact actualize. He knows all along just what He will and won’t do, and just how His free creatures will respond. So if He gambles and loses, He knows all along that He will lose. If He regrets His gamble, His regret does not come too late - it comes as early as early can be. Then nothing forces Him to go ahead with it. He has the power, and it is not too late, to actualize some other option instead.
You may well protest: if He did switch to some other option, how would He gain the foreknowledge that made Him regret His original choice? - Fair enough. My point should be put as a reductio against the supposition that God is an unlucky gambler who regrets His gamble. Suppose for reductio that God actualizes a certain option 0 ; and 0 turns out badly; and the prospect for some other option is better than 0 is when 0 turns out badly. Then God knows by foreknowledge that 0 turns out badly, so He prefers some other option to 0. Then He actualizes another option instead of 0 .Contradiction.
God is not, we may conclude, an unlucky gambler who regrets His gamble. He may yet be an unlucky gambler who does not regret His gamble, even though He lost. How might that be?
God might know that the gamble He lost still, even when lost, surpasses the expected valueI5of all the other gambles He might have tried instead, as well as the mediocre options in which He doesn’t gamble at all. That could be so if He lost, but much less badly than He might have done. He would have no cause for regret if He took one of the gambles with the best expected value (or near enoughI6)and the actual outcome was no worse than the expected value. But on this hypothesis gambling on significant freedom is a much more dangerous game than we would have suspected just on the basis of the evil-doing that actually happens. That makes it all the harder to believe that freedom is worth the risk.
Or instead, God might not regret the gamble He lost because, somehow, He knows that if He had tried any other gamble, He would still have lost, and lost at least as badly as He actually did.