No, I don't quite think that choices are least free when they have most consequences. I think they are least free when the pressure on the person choosing to choose one way or the other is greatest. Actually, even that isn't quite right. Let me make a mathematical analogy, since you're a mathmo :-). Suppose you flip a biased coin. The entropy of the result -- the average amount of information in it -- is - p log p - (1-p) log (1-p), which is biggest when p = 1/2 and tiny when p is very close to 0 or 1. But if the coin actually comes up the unexpected way, the amount of information in *that* result is very large. Similarly: a choice made under strong pressure is, on average, not very free; if you actually manage to make the "unexpected" choice then it's a more-than-averagely free choice, but usually you don't and on balance it ends up being less free. I actually think the analogy with entropy is quite close, but I'm prepared to be persuaded that there's a major problem with it :-).
Large consequences aren't quite the same thing as high pressure. Firstly, because we care more about some consequences than others. In those compelling fictional moments of choice, the usual setup is that the hero has a lot of pressure on him (it's usually him rather than her) to choose the "wrong" way. So he ends up choosing the right way despite the pressure, which is why it feels like a particularly big and genuinely-chosen choice. Secondly, because there are other forms of pressure; for instance, force of habit (can our hero resist the urge for another cigarette when the smoke may be seen by the enemy?), social norms (can our hero work together with a member of the tribe he's been brought up to hate?), moral constraints (can our hero kill an innocent child in cold blood when it's the only way to save the galaxy?), bodily demands (can our hero keep going despite the tiredness and hunger? can he resist the seductions of the voluptuous enemy agent?), and so on.
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Large consequences aren't quite the same thing as high pressure. Firstly, because we care more about some consequences than others. In those compelling fictional moments of choice, the usual setup is that the hero has a lot of pressure on him (it's usually him rather than her) to choose the "wrong" way. So he ends up choosing the right way despite the pressure, which is why it feels like a particularly big and genuinely-chosen choice. Secondly, because there are other forms of pressure; for instance, force of habit (can our hero resist the urge for another cigarette when the smoke may be seen by the enemy?), social norms (can our hero work together with a member of the tribe he's been brought up to hate?), moral constraints (can our hero kill an innocent child in cold blood when it's the only way to save the galaxy?), bodily demands (can our hero keep going despite the tiredness and hunger? can he resist the seductions of the voluptuous enemy agent?), and so on.